JPS6289675A - Clathrate complex including glycidyl compound - Google Patents
Clathrate complex including glycidyl compoundInfo
- Publication number
- JPS6289675A JPS6289675A JP23068885A JP23068885A JPS6289675A JP S6289675 A JPS6289675 A JP S6289675A JP 23068885 A JP23068885 A JP 23068885A JP 23068885 A JP23068885 A JP 23068885A JP S6289675 A JPS6289675 A JP S6289675A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- glycidyl
- formula
- group
- glycidyl compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 glycidyl compound Chemical class 0.000 title claims abstract description 11
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 21
- 238000006116 polymerization reaction Methods 0.000 abstract description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 10
- 239000013078 crystal Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 1
- KDSVXIGJVLFKOE-UHFFFAOYSA-N 2-(ethylsulfanylmethyl)oxirane Chemical compound CCSCC1CO1 KDSVXIGJVLFKOE-UHFFFAOYSA-N 0.000 description 1
- QYYCPWLLBSSFBW-UHFFFAOYSA-N 2-(naphthalen-1-yloxymethyl)oxirane Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1CO1 QYYCPWLLBSSFBW-UHFFFAOYSA-N 0.000 description 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JMSRBKPMLUGHCR-UHFFFAOYSA-N bromohydrin Chemical compound BrC[C]1CO1 JMSRBKPMLUGHCR-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UDWJHJCNPWCOTJ-UHFFFAOYSA-N isosidol Natural products CC(=O)OC1CCC2(C)C3CCC4CC3(C=C4C)C(O)CC2C1(C)CO UDWJHJCNPWCOTJ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- URYGFDRDSYOMTO-UHFFFAOYSA-N oxiran-2-ylmethyl 2-naphthalen-1-yloxyacetate Chemical compound C=1C=CC2=CC=CC=C2C=1OCC(=O)OCC1CO1 URYGFDRDSYOMTO-UHFFFAOYSA-N 0.000 description 1
- JUVGLPRIQOJMIR-UHFFFAOYSA-N oxiran-2-ylmethyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OCC1CO1 JUVGLPRIQOJMIR-UHFFFAOYSA-N 0.000 description 1
- JKXONPYJVWEAEL-UHFFFAOYSA-N oxiran-2-ylmethyl acetate Chemical compound CC(=O)OCC1CO1 JKXONPYJVWEAEL-UHFFFAOYSA-N 0.000 description 1
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- YLNSNVGRSIOCEU-UHFFFAOYSA-N oxiran-2-ylmethyl butanoate Chemical compound CCCC(=O)OCC1CO1 YLNSNVGRSIOCEU-UHFFFAOYSA-N 0.000 description 1
- YEARBAZDKOUUAM-UHFFFAOYSA-N oxiran-2-ylmethyl naphthalene-1-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)OCC1CO1 YEARBAZDKOUUAM-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- QNAJAJLBHMMOJB-UHFFFAOYSA-N oxiran-2-ylmethyl propanoate Chemical compound CCC(=O)OCC1CO1 QNAJAJLBHMMOJB-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- FNEXYKFLYBHKOC-JHMJXZSVSA-N sidol Chemical compound C1C[C@H](C2)C(=C)C[C@@]32[C@@H](O)C[C@@H]2[C@](COC(=O)C)(O)[C@H](OC(C)=O)CC[C@@]2(C)[C@@H]31 FNEXYKFLYBHKOC-JHMJXZSVSA-N 0.000 description 1
- OWFBYNFTXVLIMJ-UHFFFAOYSA-N sidol Natural products CC(=O)OC1CCC2(C)C3CCC4CC3(CC4=C)C(O)CC2C1(C)CO OWFBYNFTXVLIMJ-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
Landscapes
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（発明の技術分野）
本発明はグリシジル化合物を取り込んで生成する、安定
であると共に容易にグリシジル化合物を放出できるグリ
シジル化合物取り込み鏡体（いわゆる包接化合物）に関
する。DETAILED DESCRIPTION OF THE INVENTION (Technical Field of the Invention) The present invention relates to a glycidyl compound-incorporating mirror (a so-called clathrate compound) that is produced by incorporating a glycidyl compound and is stable and can easily release the glycidyl compound.
（従来技術）
有機化合物間の取り込み鏡体は既にいくつか知られてお
り、これらの鏡体については取り込まれた化合物（ゲス
ト（ｑｔＪｅｓｔ）化合物）の反応性が自由な時の状態
の反応性と異なることに興味がもたれている。また一方
、化合物の精製中通を目的としてこの種の錯体を利用し
ようとする試みもめる。(Prior art) Some mirrors for incorporating organic compounds are already known, and for these mirrors, the reactivity of the incorporated compound (guest (qtJest) compound) is different from the reactivity of the free state. I'm interested in different things. On the other hand, attempts are also being made to utilize this type of complex for the purpose of purifying compounds.
本発明者らは１，１，６．６−テトラフェニルヘキサ−
２，４−ジイン−１，６−シオールをホスト（ｈｏｓｔ
）化合物として種々の化合物と結晶性の錯体を形成させ
たことを既に報告したげｅｔｒａｈｅｄｒｏｎしｅｔｔ
、 １９６８，３６９５ 、１９８１，２２，３８
６５、 Ｊ、ｃｈｅｍ、Ｓｏｃ、Ｊｐｎ １９８３，
２３９）。しかしながら、本発明のようなフェノール誘
導体とグリシジル化合物との組合せによる取込み錯体に
ついては全く知られていない。グリシジル化合物は有機
合成化学上重要な中間体であり、また高分子合成化学に
おいても重要なモノマーでおる。これらのグリシジル化
合物は種類によっては高純度で得ることは必ずしも容易
ではない。またグリシジル化合物の重合反応における取
込み鏡体の効果も新規なポリマ〜を製造する上で非常に
関心がもたれるところである。The present inventors have obtained 1,1,6,6-tetraphenylhex-
2,4-diyne-1,6-thiol as host
) It has already been reported that etrahedron formed crystalline complexes with various compounds.
, 1968, 3695 , 1981, 22, 38
65, J, chem, Soc, Jpn 1983,
239). However, an uptake complex formed by a combination of a phenol derivative and a glycidyl compound as in the present invention is not known at all. Glycidyl compounds are important intermediates in organic synthesis chemistry, and are also important monomers in polymer synthesis chemistry. Depending on the type of these glycidyl compounds, it is not always easy to obtain them with high purity. Furthermore, the effect of the incorporated mirror in the polymerization reaction of glycidyl compounds is of great interest in the production of new polymers.
（発明の目的）
本発明は有機合成化学上各種の応用が考えられる、特に
高純度の中間体もしくは重合田七ツマ−としてのグリシ
ジル化合物を得るための、または新しい反応性を示す中
間体もしくは重合田七ツマ−としての新規なグリシジル
化合物取り込み錯体を提供することを目的とする。(Objective of the Invention) The present invention has various applications in organic synthetic chemistry, particularly for obtaining glycidyl compounds as highly pure intermediates or polymerization compounds, or for producing intermediates or polymers that exhibit new reactivity. The purpose of the present invention is to provide a novel glycidyl compound-incorporating complex.
（発明の構成）
本発明は、下記一般式（Ｉ）で示されるグリシジル化合
物
す
（但し、（Ｉ＞式において、Ｒは水素原子又はメチル基
を表わす。Ｘはヒドロキシ基、アルコキシ基、アシル基
、アシルオキシ基、アルコキシカルボニル曇、シアノ基
及びアルキルチオ基から選ばれる基又はハロゲン原子を
表わす。）と下記式（ｎ）で示される１、１−ビス （
ｐ−ヒドロキシフェニル）−シクロヘキサンとによって
形成されてなるグリシジル化合物取り込み錯体て必る。(Structure of the Invention) The present invention relates to a glycidyl compound represented by the following general formula (I) (wherein R represents a hydrogen atom or a methyl group, and X represents a hydroxy group, an alkoxy group, an acyl group). , an acyloxy group, an alkoxycarbonyl cloud, a cyano group, and an alkylthio group, or a halogen atom) and 1,1-bis (
(p-hydroxyphenyl)-cyclohexane.
本発明においてゲスト化合物となるグリシジル化合物と
しては、グリシドール、エピクロルヒドリン、エビブロ
モヒドリン、β−メチルエピクロルヒドリン、アリルグ
リシジルエーテル。Glycidyl compounds serving as guest compounds in the present invention include glycidol, epichlorohydrin, shrimp bromohydrin, β-methylepichlorohydrin, and allyl glycidyl ether.
ブチルグリシジルエーテル、フェニルグリシジルエーテ
ル、０−メチルフェニルグリシジルエーテル、ナフチル
グリシジルエーテル、酢酸グリシジル、プロピオン酸グ
リシジル、酪酸グリシジル、安息香酸グリシジル、ケイ
皮酸グリシジル、アクリル酸グリシジル、メタクリル酸
グリシジル、ナフトエ酸グリシジル、ナフトキシ酢酸グ
リシジル、エチルグリシジルチオエーテル、ω−エポキ
シ酪酸エチルなどが挙げられる。Butyl glycidyl ether, phenyl glycidyl ether, 0-methylphenyl glycidyl ether, naphthyl glycidyl ether, glycidyl acetate, glycidyl propionate, glycidyl butyrate, glycidyl benzoate, glycidyl cinnamate, glycidyl acrylate, glycidyl methacrylate, glycidyl naphthoate, Examples include glycidyl naphthoxyacetate, ethylglycidylthioether, and ethyl ω-epoxybutyrate.
本発明においてホスト化合物となる（■）式化合物は既
に知られており、シクロヘキサンとフェノールを酸触媒
で縮合させることによって容易にＩＡ造できる［Ｊ、Ａ
ｍ、Ｃｈｅｍ、Ｓｏｃ、 ６１１７８５（１９３９月
。The compound of the formula (■) which serves as the host compound in the present invention is already known, and IA can be easily produced by condensing cyclohexane and phenol with an acid catalyst [J, A
m, Chem, Soc, 611785 (1939.
本発明において（Ｉ）式化合物と（ＩＩ）式化合物から
鏡体を形成させるには、これら両者を直接混合してもよ
いし、溶媒を用いて反応させてもよい。溶媒としては脂
肪族炭化水素類、芳香族炭化水素類、エーテル類の単独
もしくはこれらの混合物が適当である。反応温度や反応
時間は上記（１）式、（■）式の化合物の組合わせによ
って異なるが、通常室温乃至溶媒の還流温度の範囲が適
当でおる。反応時間は鏡体形成による沈澱によって容易
に定められる。In the present invention, in order to form a mirror body from the compound of formula (I) and the compound of formula (II), the two may be directly mixed or may be reacted using a solvent. Suitable solvents include aliphatic hydrocarbons, aromatic hydrocarbons, and ethers alone or in mixtures thereof. The reaction temperature and reaction time vary depending on the combination of the compounds of formulas (1) and (■), but are usually in the range of room temperature to the reflux temperature of the solvent. The reaction time is easily determined by precipitation due to mirror formation.
錯体は使用する（Ｉ）式化合物と（ＩＩ）式化合物の組
合わせによって異なるが、通常（１）式化合物と（ｎ）
式化合物のモル比が３１〜１．３の割合の化合物として
生成する。The complex differs depending on the combination of the formula (I) compound and the formula (II) compound used, but it usually consists of the formula (1) compound and (n).
It is produced as a compound having a molar ratio of the formula compound from 31 to 1.3.
得られた鏡体は同感結晶であり、これを再結晶によって
精製することが可能である。またこの鏡体を加熱蒸溜、
極性溶媒による置換、クロマトグラフィーなどの手段に
よって分解させて特異な性質を有するグリシジル化合物
を取り出すこともてきる。The obtained mirror body is a sympathic crystal, which can be purified by recrystallization. In addition, this mirror body is heated and distilled,
Glycidyl compounds with unique properties can also be extracted by decomposition by means such as substitution with polar solvents and chromatography.
（発明の効果）
本発明の鏡体は新規な化合物であり、安定性に優れると
共に通常の手段によって特異な性質をもった有用なグリ
シジル化合物を極めて容易に放出することができる。(Effects of the Invention) The mirror of the present invention is a novel compound that has excellent stability and can extremely easily release useful glycidyl compounds with unique properties by ordinary means.
（実施例）
実施例１
１．１−ビス（ｐ−ヒドロキシフェニル〉−シクロヘキ
サン２．ＯｇをグＩＪシドール２０ｍ１に加熱溶解し、
その後室温で１２時間放置したところ無色針状結晶２．
２０が析出した。この結晶は融点１７５〜１８１°Ｃで
原料化合物のモル比が１．１の錯体であることが確めら
れた。(Example) Example 1 2.0 g of 1.1-bis(p-hydroxyphenyl>-cyclohexane was dissolved in 20 ml of GuIJ Sidol by heating,
After that, it was left to stand at room temperature for 12 hours, resulting in colorless needle crystals.
20 was precipitated. It was confirmed that this crystal was a complex with a melting point of 175 to 181°C and a molar ratio of the raw material compound to 1.1.
実施例２〜５
表１に示すグリシジル化合物を用いた以外は実施例１と
同様にして錯体を製造した。なあ、これらの錯体はいず
れも分解のため融点か不明確でおった。Examples 2 to 5 Complexes were produced in the same manner as in Example 1 except that the glycidyl compounds shown in Table 1 were used. Incidentally, the melting points of all these complexes were unclear due to decomposition.
表 １
上記実施例１〜５によって得られた鏡体の赤外線吸収ス
ペクトルを第１図〜第５図に示した。Table 1 The infrared absorption spectra of the mirror bodies obtained in Examples 1 to 5 above are shown in FIGS. 1 to 5.
第１図〜第５図はそれぞれ実施例１〜実施例５によって
１ｑられた錯体の赤外線吸収スペクトルである。FIGS. 1 to 5 are infrared absorption spectra of the complexes prepared by 1q according to Examples 1 to 5, respectively.
Claims (1)
II）で示される１，１−ビス（ｐ−ヒドロキシフェニル
）−シクロヘキサンとによつて形成されてなるグリシジ
ル化合物取り込み錯体。 ▲数式、化学式、表等があります▼（ I ） （但し、（ I ）式において、Ｒは水素原子又はメチル
基を表わす。Ｘはヒドロキシ基、アルコキシ基、アシル
基、アシルオキシ基、アルコキシカルボニル基、シアノ
基及びアルキルチオ基から選ばれる基又はハロゲン原子
を表わす。）▲数式、化学式、表等があります▼（II）[Claims] A glycidyl compound represented by the following general formula (I) and the formula (
II) and 1,1-bis(p-hydroxyphenyl)-cyclohexane. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (However, in formula (I), R represents a hydrogen atom or a methyl group. X represents a hydroxy group, an alkoxy group, an acyl group, an acyloxy group, an alkoxycarbonyl group, Represents a group selected from a cyano group and an alkylthio group or a halogen atom.) ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ (II)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23068885A JPH0643409B2 (en) | 1985-10-16 | 1985-10-16 | Glycidyl compound incorporation complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23068885A JPH0643409B2 (en) | 1985-10-16 | 1985-10-16 | Glycidyl compound incorporation complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6289675A true JPS6289675A (en) | 1987-04-24 |
| JPH0643409B2 JPH0643409B2 (en) | 1994-06-08 |
Family
ID=16911750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23068885A Expired - Fee Related JPH0643409B2 (en) | 1985-10-16 | 1985-10-16 | Glycidyl compound incorporation complex |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0643409B2 (en) |
-
1985
- 1985-10-16 JP JP23068885A patent/JPH0643409B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0643409B2 (en) | 1994-06-08 |
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