JPS62201880A - 4,5,6-tri-alkyl-isobenzofuran - Google Patents
4,5,6-tri-alkyl-isobenzofuranInfo
- Publication number
- JPS62201880A JPS62201880A JP4356786A JP4356786A JPS62201880A JP S62201880 A JPS62201880 A JP S62201880A JP 4356786 A JP4356786 A JP 4356786A JP 4356786 A JP4356786 A JP 4356786A JP S62201880 A JPS62201880 A JP S62201880A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- tri
- isobenzofuran
- present
- formula
- 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.)
- Pending
Links
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は光記録用媒体として有用な９ｔ、、ｔ、ｔ −
トリーアルキル−インベンゾフラン類に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention provides 9t, t, t-
It relates to trialkyl-inbenzofurans.
近年、有機系化合物を用いた光記録に関する研究が活発
に行なわれている。In recent years, research on optical recording using organic compounds has been actively conducted.
光記録の方式としては多くの方式があるが、現在層も有
望と考えられている方式のうちの１つとして、フォトク
ロミック化合物を用いる方式がある。There are many optical recording methods, and one of the methods currently considered to be promising is a method using a photochromic compound.
即ち、下式の様にムなる化合物に特定の波長νを持つ光
を照射しＢなる化合物とする。That is, as shown in the following formula, compound B is irradiated with light having a specific wavelength ν to form compound B.
この際、下記の２つの条件
■ Ｂが安定に存在する事
■ ＡとＢの吸収が異る事
が満足？れれば、波長νの光で記録し、これをＡとＢと
を識別する事が可能な波長の光で走査して、その反射光
の変化を検知する事によ〕、読み出しが可能となる。In this case, are the following two conditions satisfied? ■ B exists stably ■ Absorption of A and B is different? If so, it would be possible to read out the information by recording it with light of wavelength ν, scanning it with light of a wavelength that makes it possible to distinguish between A and B, and detecting changes in the reflected light. .
本発明者は、かさ高い置換基で歪ませた縮合多環（複素
）芳香族化合物について研究を行なつｆｅｅｌ ｇ、
ｊ、６−トリーアルキル−イソベンゾフランが、上記の
様なフォトクロミック性を示し、光記録用媒体としての
使用が期待される事を知得し１本発明を完成するに到つ
な。The present inventor conducts research on fused polycyclic (hetero) aromatic compounds distorted with bulky substituents.
Having learned that j,6-trialkyl-isobenzofuran exhibits the above-mentioned photochromic properties and is expected to be used as an optical recording medium, we have completed the present invention.
即ち１本発明の要旨は弐ｍ
（式中、Ｒ，Ｒ及びＲは同一又は異っていてもよいアル
キル基を表わす。）
で示されるｇ、ｊ、４− ）リーアルキルーインベンゾ
フランに存する。That is, the gist of the present invention resides in g, j, 4-) arykyl-inbenzofuran represented by 2m (in the formula, R, R and R represent an alkyl group which may be the same or different).
以下本発明を説明するに１本発明のダ、ｊ、４−トリー
アルキル−イソ−ベンゾフランは１例えば、次の様な反
応式に従って製造する事ができる。The present invention will be explained below. The da,j,4-trialkyl-iso-benzofuran of the present invention can be produced, for example, according to the following reaction formula.
即？ｔ％ −２１−？１ｇ−） ！Ｊ−フルキルーシク
ロペンタジェノン（１）とアセチレンジカルボン酸ジメ
チルエステルとを１例えば？Ｏ℃で一時間程度反応嘔せ
てｊ、（ｌ、！ −）リーアルキルー７タル酸ジメチル
エステルを得、さらに、こｎｔ”エーテル中すチウムア
ルミナムヒドリド（ｂ１豆ａ４）に作用させて！、４ｔ
、！ −）リーアルキルー／、−２−ビスヒドロキシメ
チルベンゼン（Ａ） ｔ−得る。これを塩化メチレン中
無水クロム酸ピリジン錯塩で酸化することにより／−ヒ
ドロキシ−ｇ、ｊ、６−）リーアルキル−／、！−ジヒ
ドロインベンゾフラン（Ｂ）を得、これを加熱脱水する
ことによりダ、！。Immediately? t% -21-? 1g-)! For example, J-furkyl-cyclopentagenone (1) and acetylene dicarboxylic acid dimethyl ester? Reaction was carried out for about an hour at 0°C to obtain (l,! -) lyalkyl-7talic acid dimethyl ester, which was then reacted with sodium aluminum hydride (b1 bean a4) in ether.4t
,! -) Realkyl-/,-2-bishydroxymethylbenzene (A) t-obtained. By oxidizing this with anhydrous chromic acid pyridine complex salt in methylene chloride, /-hydroxy-g,j,6-)lyalkyl-/,! -Dihydroinbenzofuran (B) is obtained and dehydrated by heating. .
６−ドリーアルキル−イソベンシフランをイｑる事がで
きる。6-Dolyalkyl-isobensifuran can be obtained.
かくして得られる本発明の＜１．１．６− ）リーアル
キルーインベンゾフランはフォトクロミック性を示し、
かかる性質を利用し走光学記録用媒体としての使用が期
待される。The <1.1.6-) aryalkyl-inbenzofuran of the present invention thus obtained exhibits photochromic properties,
Utilizing such properties, it is expected to be used as a media for optical scanning recording.
以下実施例により本発明の詳細な説明する。 The present invention will be explained in detail below with reference to Examples.
実施例／
ｇ、ｊ、Ｇ −）ソーｔ−ブチル−イソベンゾフランの
合成
混合物を２０℃で／、６時間加熱し九後１反応混合物を
シリカゲルカラムクロマトで分離精製し。Example/g, j, G-) A synthesis mixture of so-t-butyl-isobenzofuran was heated at 20°C for 6 hours, and then the reaction mixture was separated and purified using silica gel column chromatography.
３．４ｔ、ｊ−トリーｔ−ブチル−フタル酸ジメチルｚ
ステル０．ｒ ｆ （／、ｊ’Ｊ’ｍｍｏｌ 、 ７
０％ ）を得意〇これをエーテル−２０１ｄ中０．２３
？ （４ｊｍｍｏｌ）のＬ１ムＩ１．Ｈ４と室温で２
時間反応させ、常法により処理し虎後、カラムクロマト
グラムによシ分離精製し０．３’ｌ ｆ （／、／ｍｍ
ｏｌ、 １０％のジオール（Ａ）を得な。ＡＯ，ｊｔｆ
ｆｌｏｄの塩化メチレンに溶解させ、ここへ乾燥塩化メ
チレンに溶かしな無水クロム酸ピリジン錯塙を／、Ｊｍ
ｍｏ１加え室温で７時間反応させな。反応混合物をその
ままシリカゲルカラム（ヘキサン／酢酸エチル−４ｔ／
／）で処理しＢ （６１ｒｑ、 ０．２２ ｍｍｏｌ、
２０ ％）を得た。3.4t, j-tri-t-butyl-dimethyl phthalate z
Stell 0. r f (/, j'J'mmol, 7
0%) Good at this ether - 0.23 in 201d
? (4jmmol) of L1muI1. H4 and 2 at room temperature
After reacting for an hour and treating in a conventional manner, it was separated and purified by column chromatography to give a concentration of 0.3'l f (/,/mm
ol, obtain 10% diol (A). AO, jtf
Dissolve flod in methylene chloride, and add chromic anhydride pyridine complex dissolved in dry methylene chloride/, Jm
Add mo1 and let it react at room temperature for 7 hours. The reaction mixture was directly transferred to a silica gel column (hexane/ethyl acetate-4t/
/) and B (61 rq, 0.22 mmol,
20%).
これを片方を封じなガラス管に入れ減圧下加熱しｕ、ｚ
、ｔ−トリーｔ−ブチルイソベンゾフラン（ｊ Ｏｔｑ
、 ０．／７６ ｍｍｏｌ、 １０％）を昇華させて精
製し虎。Place this in a glass tube with one end sealed and heat under reduced pressure u, z
, t-tri-t-butylisobenzofuran (j Otq
, 0. /76 mmol, 10%) was purified by sublimation.
分子ｊｉ Ｃ２ｏＨｓｏｏ 測定値 ２♂ｔ、２３
０／ｇ計算値 コ／４．２２り乙３
’Ｈ−ＭＭＲ（ＣＤｓＣＮ） δ 乙♂ｊ （
ｑ、 −ＩＨ）６、り６ （ｏ、 ／Ｈ’）
／、ｓｊ （ｓ、 タＨ）
／、３７ （ｓ、 ？Ｈ）
ｔ、３９ｔ （ｓ、 ワＨ）
前記実施例に順じて得られる”＃−ｊｌ’ Ｉ”）−
アルキル−イソベンゾフランにアセトニトリル中−７０
℃で高圧水銀灯硫酸調水溶液透過光を照射する事により
定量的収率で下記式〔…〕で表わされる安定なバレン誘
漕体を得る事ができな。Molecule ji C2oHsoo Measured value 2♂t, 23
0/g calculated value Ko/4.22 ri Otsu 3 'H-MMR (CDsCN) δ Otsu♂j (
q, -IH)6, ri6 (o, /H') /, sj (s, taH) /, 37 (s, ?H) t, 39t (s, waH) According to the above example Obtained "#-jl'I")-
Alkyl-isobenzofuran-70 in acetonitrile
By irradiating a high-pressure mercury lamp with transmitted light from a sulfuric acid aqueous solution at ℃, it was not possible to obtain a stable barene dicarbonate represented by the following formula [...] in quantitative yield.
参考例
ｇ、ｒ、６−） ＩＪ −ｔ−７’チルイソベンゾフラ
ン２０ｍｇを０．３ｄの重アセトニトリルに溶解し、コ
ルク製のｎｍｒサンプル管に脱気封管し、硫酸銅溶液フ
ィルターを用いて間圧水銀灯（３００Ｗ）装置に！分間
かざした後、溶媒を留去して定量的収率でバレン訪導体
を得た。電子スペクトルを測定した結果、出発物質にお
いて認められ九ＪＪＯｎｍの極大吸収が完全に消失した
。Reference examples g, r, 6-) 20 mg of IJ-t-7' thylisobenzofuran was dissolved in 0.3 d of deuterated acetonitrile, degassed and sealed in a cork nmr sample tube, and dissolved using a copper sulfate solution filter. For pressure mercury lamp (300W) equipment! After standing for a minute, the solvent was distilled off to obtain the barene conductor in quantitative yield. As a result of measuring the electronic spectrum, the maximum absorption of 9JJOnm observed in the starting material completely disappeared.
分子量 ０．Ｈ８ｏＯ測定値 ２／４．２２？り！計算
値 コ／乙、ココ２６３
’Ｈ−ＨＭＲ（ＣＤ（：！ｆｉ２） δ ／、２
／ （ｎ、 ／７Ｈ）／、２？（ｓ、 タ１Ｋ）
２．０／（ｓ、 ／Ｈ）
４．７／（ｓ、 、２Ｈ）
〔発明の効果〕
本発明のｕ、ｊ、１ａ−）ソーアルキル−インベンゾフ
ラン類は、情報材料分野１例えば光記録用媒体としての
使用が期待される。Molecular weight 0. H8oO measurement value 2/4.22? the law of nature! Calculated value Ko/Otsu, Koko263'H-HMR(CD(:!fi2) δ/, 2
/ (n, /7H)/, 2? (s, ta 1K) 2.0/(s, /H) 4.7/(s, , 2H) [Effects of the invention] The u, j, 1a-) so-alkyl-inbenzofurans of the present invention are Material Field 1: For example, it is expected to be used as an optical recording medium.
Claims (1)
ても良いアルキル基を表わす。） で示される４，５，６−トリ−アルキル−イソベンゾフ
ラン類。(1) The following general formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼…………[I] (In the formula, R^1, R^2 and R^3 may be the same or different. 4,5,6-tri-alkyl-isobenzofurans represented by (representing an alkyl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4356786A JPS62201880A (en) | 1986-02-28 | 1986-02-28 | 4,5,6-tri-alkyl-isobenzofuran |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4356786A JPS62201880A (en) | 1986-02-28 | 1986-02-28 | 4,5,6-tri-alkyl-isobenzofuran |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62201880A true JPS62201880A (en) | 1987-09-05 |
Family
ID=12667320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4356786A Pending JPS62201880A (en) | 1986-02-28 | 1986-02-28 | 4,5,6-tri-alkyl-isobenzofuran |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62201880A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010524865A (en) * | 2007-04-19 | 2010-07-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Process for the preparation of substituted pentacenes |
-
1986
- 1986-02-28 JP JP4356786A patent/JPS62201880A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010524865A (en) * | 2007-04-19 | 2010-07-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Process for the preparation of substituted pentacenes |
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