JPH0142250B2 - - Google Patents

Info

Publication number: JPH0142250B2
Authority: JP; Japan
Prior art keywords: tricyclo; ene; endo; formula; decane
Prior art date: 1981-12-21
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.): Expired

Application number

JP20674581A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58109429A (ja

Inventor

Naotake Takaishi

Yoshiaki Fujikura

Yoshiaki Inamoto

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Kao Corp

Original Assignee

Kao Corp

Priority date (The priority date 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 date listed.)

1981-12-21

Filing date

1981-12-21

Publication date

1989-09-11

1981-12-21 Application filed by Kao Corp filed Critical Kao Corp

1981-12-21 Priority to JP20674581A priority Critical patent/JPS58109429A/ja

1983-06-29 Publication of JPS58109429A publication Critical patent/JPS58109429A/ja

1989-09-11 Publication of JPH0142250B2 publication Critical patent/JPH0142250B2/ja

Status Granted legal-status Critical Current

Links

AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000000034 method Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
239000003205 fragrance Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
235000019568 aromas Nutrition 0.000 description 2
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
YKNMBTZOEVIJCM-UHFFFAOYSA-N dec-2-ene Chemical compound CCCCCCCC=CC YKNMBTZOEVIJCM-UHFFFAOYSA-N 0.000 description 1
GVRWIAHBVAYKIZ-UHFFFAOYSA-N dec-3-ene Chemical compound CCCCCCC=CCC GVRWIAHBVAYKIZ-UHFFFAOYSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000002304 perfume Substances 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000007070 tosylation reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fats And Perfumes (AREA)

JP20674581A 1981-12-21 1981-12-21 新規トリシクロ〔５．２．１．０↑２，↑６〕デセン Granted JPS58109429A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP20674581A JPS58109429A (ja)	1981-12-21	1981-12-21	新規トリシクロ〔５．２．１．０↑２，↑６〕デセン

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP20674581A JPS58109429A (ja)	1981-12-21	1981-12-21	新規トリシクロ〔５．２．１．０↑２，↑６〕デセン

Publications (2)

Publication Number	Publication Date
JPS58109429A JPS58109429A (ja)	1983-06-29
JPH0142250B2 true JPH0142250B2 (pl)	1989-09-11

Family

ID=16528389

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP20674581A Granted JPS58109429A (ja)	1981-12-21	1981-12-21	新規トリシクロ〔５．２．１．０↑２，↑６〕デセン

Country Status (1)

Country	Link
JP (1)	JPS58109429A (pl)

1981
- 1981-12-21 JP JP20674581A patent/JPS58109429A/ja active Granted

Also Published As

Publication number	Publication date
JPS58109429A (ja)	1983-06-29

Publication	Publication Date	Title
Kabalka et al.	1975	New mild conversion of ketones to the corresponding methylene derivatives
JP2022036968A (ja)	2022-03-08	３－ヒドロキシ－３，６－ジメチルヘキサヒドロベンゾフラン－２－オンおよびその誘導体の製造
Kuehne et al.	1973	Cyclopropylamines as intermediates in a new method for alkylation of aldehydes and ketones
Cope et al.	1963	Proximity Effects. XXXIV. Solvolysis of cis-Bicyclo [6.1. 0] nonane
US3318945A (en)	1967-05-09	Cyclododecadiene carboxylic acid esters
US3770836A (en)	1973-11-06	Cyclopropyl cyclohexanes
Aaron et al.	1968	Synthesis of the eight stereoisomers of a tetrahydrocannabinol congener
US3718696A (en)	1973-02-27	Process for the preparation of macrocyclic compounds and novel compounds produced thereby
JPH0246590B2 (pl)	1990-10-16
Franzus et al.	1968	Synthesis of exo, exo-5, 6-dideuterio-syn-7-acetoxy-norbornene and exo, exo-k, 6-dideuterio-2-norbornene
Chaco et al.	1962	Azo and Hydrazo Aliphatic Acid Derivatives. I. Alkylazoformic Acid Esters1
US4011269A (en)	1977-03-08	Process for the preparation of sesquiterpenic derivatives
JP2558329B2 (ja)	1996-11-27	水素化方法
JPS58109429A (ja)	1983-06-29	新規トリシクロ〔５．２．１．０↑２，↑６〕デセン
Taylor	1972	Convenient synthesis of barrelene
Matsumoto et al.	1971	The Stereochemistry of Nucleophilic Addition. I. The Reformatsky Reaction of 2-Methyl-and 2-Ethylcyclohexanones
KR850000046B1 (ko)	1985-02-14	1rs, 4sr, 5rs-4-(4,8-디메틸-5-히드록시-7-노넨-1-일)-4-메틸-3,8-디옥사비시클로[3.2.1]옥탄-1-아세트산의 전합성 방법
JPH045656B2 (pl)	1992-02-03
JPH056600B2 (pl)	1993-01-26
Harding et al.	1978	Studies on allenes as participants in cationic π-cyclizations
Gutsche et al.	1967	Ring enlargements. XII. N-Nitrosolactams as ring-enlargement reagents
Tsukasa	1989	A new synthesis of rosefuran
JPS62482A (ja)	1987-01-06	プロスタサイクリン類
EP0297510B1 (en)	1992-03-18	Bornane-3-spiro-1'-cyclopentane derivatives and perfumery compositions containing them
House et al.	1965	Perhydroindan Derivatives. VI. Derivatives of 1, 1a, 2, 3, 4, 4a-Hexahydrofluorene-2, 9-dione1