Asymmetric induction catalytic synthesis method for L-muscone

A technique of inducing catalysis and synthesis methods, applied in asymmetric synthesis, organic chemistry methods, chemical instruments and methods, etc., can solve problems that have not been reported in the literature, and achieve high optical purity, mild reaction conditions, and high economic benefits

Inactive Publication Date: 2010-10-20
DALIAN ZHAOYI BIOLOGY KETONE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the artificial synthesis method of L-MUSCONE we use has not been reported in the literature at home and abroad.

Method used

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  • Asymmetric induction catalytic synthesis method for L-muscone
  • Asymmetric induction catalytic synthesis method for L-muscone
  • Asymmetric induction catalytic synthesis method for L-muscone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (1): Synthesis of N-(3-methyl-cyclopentadecenyl)benzylamine

[0043] A water separator was installed in the three-necked flask. Condenser. dryer. After the thermometer is installed, add: benzene, MUSCONE, and amine in turn. The ratio of the material is: 100ml.5.2g (0.02mol). 2.5g (0.02mol). ) p-toluenesulfonic acid, continue to heat up to the reflux temperature to remove the moisture in the reaction to: 0.5-5ppm. use Na 2 CO 3 10%. Washing with aqueous solution, washing with water until neutral; anhydrous MgSO 3 Dry and evaporate the solvent under reduced pressure to obtain the crude product and purify it by column chromatography;

[0044] The product is:

[0045] Slightly yellow to yellow oily liquid 4.5g, yield 71.40%.

[0046] vmax(film)1644 -1 (C=N)

[0047] HNMR:

[0048] (CDCl 3 ): δ0.933~0.973 (3HlJ 66 h 3 CH 3 ): 1.231~1.44226H (d CH2-: 4.47 (2H brsCH 2 N): 7.13 (5H mph)

[0049] MF: C 23 h 37 Nmw: 327

[0050] N-(3-Methyl-cyclopentadecenyl)b...

Embodiment 2

[0071] 1): Synthesis of N-(3-methyl-cyclopentadecenyl)benzylamine

[0072] Put benzene, MUSCONE and amine into the container in turn, the ratio of the three materials is 5L:1mol:1mol; after stirring for 10min at 17~25°C, add p-toluenesulfonic acid after heating up to 60°C, p-toluenesulfonic acid and The mol ratio of MUSCONE is 1: 0.08; Continue to heat up to reflux temperature, remove the moisture in the reaction to: 0.5-5ppm; Use Na 2 CO 3 10%. Aqueous solution washing, water washing neutral; anhydrous MgSO 3 Dry and evaporate the solvent under reduced pressure to obtain the crude product and purify it by column chromatography to obtain N-(3-methyl-cyclopentadecenyl)benzylamine;

[0073] 2): Synthesis of L-MUSCONE

[0074] Described second step reaction is specifically: reactor uses N 2 After replacement, add C in sequence 2 h 5 OH, N-(3-methyl-cyclopentadecenyl)benzylamine, CH 2 Cl 2 and [RuC 12 .[(R)-BINAP] 2 ET 3 Access to H 2 The material ratio is 28L: 1.2mol:...

Embodiment 3

[0076] 1): Synthesis of N-(3-methyl-cyclopentadecenyl)benzylamine

[0077] Put benzene, MUSCONE and amine into the container in turn, the ratio of the three materials is 5L:1mol:1mol; after stirring for 10min at 17~25°C, add p-toluenesulfonic acid after heating up to 60°C, p-toluenesulfonic acid and The mol ratio of MUSCONE is 1: 0.08; Continue to heat up to reflux temperature, remove the moisture in the reaction to: 0.5-5ppm; Use Na 2 CO 3 10wt%.CH 2 Cl 2 Concentrate, wash and extract to neutral; anhydrous MgSO 3 Dry and evaporate the solvent under reduced pressure to obtain the crude product and purify it by column chromatography to obtain N-(3-methyl-cyclopentadecenyl)benzylamine;

[0078] 2): Synthesis of L-MUSCONE

[0079] Described second step reaction is specifically: reactor uses N 2 After replacement, add C in sequence 2 h 5 OH, N-(3-methyl-cyclopentadecenyl)benzylamine, CH 2 Cl 2 and [RuC 12 .[(R)-BINAP] 2 ET 3 Access to H 2; The material ratio is 32L: ...

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Abstract

The invention discloses an asymmetric induction catalytic synthesis method for L-muscone. The L-muscone is prepared by performing asymmetric induction catalytic synthesis on N-3-methyl-cyclopentadecane alkenyl benzylamine which is obtained by asymmetrically converting a racemate compound for multiple times and used as raw materials in the presence of an organo-transition metal complex inducing catalyst. The method has the prominent advantages of high economic benefit, simple synthesis process and low synthesis temperature.

Description

technical field [0001] The invention belongs to the development and research technology of artificial synthetic substitutes of endangered wild animals and plants, and specifically relates to a method for organic chemical synthesis of L-MUSCONE (L-Muscone). Background technique [0002] Musk (shè) incense is the secretion of the glandular sac between the navel and genitals of male musk deer. It is granular or massive after drying, and has a special aroma and bitter taste. Musk is a very rare and rare medicinal material. Among natural musk The main bioactive ingredient and aroma center is muscone. There are 298 kinds of patent medicines in my country’s Chinese patent medicine catalog that need to be compatible with musk. One out of every 23 pharmaceutical factories in China’s more than 6,000 pharmaceutical factories will use this raw material. Wan", "Niuhuang Qingxin Wan", "Yunnan Baiyao", "Pianzihuang" and "Mayinglong Musk Ointment" from Yunnan Pharmaceutical Factory. In 200...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/385C07C45/71C07C45/51C07B53/00B01J31/22
Inventor 王亚龙陈深坤
Owner DALIAN ZHAOYI BIOLOGY KETONE TECH
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