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Synthesis process of trans-menthyl-2, 8-diene-1-ol

A synthetic technique, a menthyl-based technique, which is applied in the field of synthetic technique of trans-menthol-2,8-dien-1-ol, can solve problems such as not seen, and achieve the effect of improving chiral purity and yield

Active Publication Date: 2019-05-10
JIANGSU JIMING PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for limonene, a compound with a diolefin structure, the use of biocatalysis to prepare high-position (1,2-position) selectivity and cis-trans-selective epoxidation of limonene has not been reported, let alone the use of biocatalysis to prepare high Purity 1,2-epoxylimonene, and then a literature report on the synthesis of high-purity trans-menthyl-2,8-dien-1-ol

Method used

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  • Synthesis process of trans-menthyl-2, 8-diene-1-ol
  • Synthesis process of trans-menthyl-2, 8-diene-1-ol
  • Synthesis process of trans-menthyl-2, 8-diene-1-ol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] A kind of synthetic technique of trans-menthyl-2,8-dien-1-ol, it comprises the steps:

[0041] (1) Add Humicolasp. lipase 48g to the mixed system of (+)-limonene 1.2Kg, purified water 4L and myristic acid 205g, and then slowly pump in 1.1L of 30% hydrogen peroxide at 23°C to control The pumping time is 16 hours. After the pumping, continue to react for 2 hours to stop the reaction, add a 16.7% sodium sulfite aqueous solution to quench, extract with methyl tert-butyl ether, separate liquids twice, combine the obtained organic phases, and sequentially use saturated Sodium bicarbonate aqueous solution and washing with water, and finally the organic phase after washing with water was distilled under reduced pressure to obtain 761 g of trans-1,2-epoxylimonene (purity 91.4%, yield 57%; cis-1,2-epoxylimonene content 1.6 %).

[0042] (2) Under the protection of nitrogen, mix 843g of diphenyl diselenide and 7.6L of absolute ethanol, the temperature drops to 8°C, add 234g of sod...

Embodiment 2

[0047] A kind of synthetic technique of trans-menthyl-2,8-dien-1-ol, its difference with embodiment 1 is:

[0048] (1) Add Humicolasp. lipase 600g to the mixed system of (+)-limonene 1.2Kg, purified water 4L and myristic acid 205g, then slowly pump in 1.1L of 30% hydrogen peroxide at 23°C to control The pumping time is 16 hours. After the pumping, continue to react for 2 hours to stop the reaction, add a 16.7% sodium sulfite aqueous solution to quench, extract with methyl tert-butyl ether, separate liquids twice, combine the obtained organic phases, and sequentially use saturated Sodium bicarbonate aqueous solution and water washing, finally obtain 745g trans 1,2-epoxy limonene (purity 90.1%, yield 56%; cis 1,2-epoxy limonene 1.8% );

[0049] (3) Finally, 501 g of trans-menthyl-2,8-dien-1-ol was obtained (purity 95.0%, ee% 99.0%,

[0050] de% 99.1%).

[0051] The overall yield of the reaction from compound 2 (1,2-epoxylimonene) to compound 5 (trans-menthyl-2,8-dien-1-ol) wa...

Embodiment 3

[0054] A kind of synthetic technique of trans-menthyl-2,8-dien-1-ol, its difference with embodiment 1 is:

[0055] (1) Add Humicolasp. lipase 48g to the mixed system of (+)-limonene 1.2Kg, purified water 4L and myristic acid 205g, and then slowly pump in 2.2L of 30% hydrogen peroxide at 23°C to control The pumping time is 24 hours. After the pumping, continue to react for 2 hours to stop the reaction, add 16.7% sodium sulfite aqueous solution to quench, extract with methyl tert-butyl ether, separate liquid twice, combine the obtained organic phases, and sequentially use saturated Sodium bicarbonate aqueous solution and water washing, finally obtain 776g trans-1,2-epoxylimonene (purity 89.2%, yield 54%; cis-1,2-epoxylimonene 2.3% );

[0056] (3) Finally, 516 g of trans-menthyl-2,8-dien-1-ol was obtained (purity 97.0%, ee% 98.4%, de% 98.9%).

[0057] The overall yield of the reaction from compound 2 (1,2-epoxylimonene) to compound 5 (trans-menthyl-2,8-dien-1-ol) was 65%.

[0...

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Abstract

The invention belongs to the technical field of preparation of trans-menthyl-2, 8-diene-1-ol, and particularly relates to a synthesis process of trans-menthyl-2, 8-diene-1-ol. The synthesis process comprises the following steps: (1) taking limonene as a raw material, and carrying out lipase catalytic oxidation to prepare 1, 2-epoxy limonene; (2) ring-opening the 1, 2-epoxy limonene in the presenceof sodium borohydride and diphenyl diselenide to form limonene selenide; (3) forming selenium oxide under the action of an oxidizing agent by the limonene selenide and then carrying out elimination reaction to prepare the trans-menthyl-2, 8-diene-1-ol. According to the invention, the 1, 2-epoxy limonene is firstly prepared by a lipase catalysis method with high chiral selectivity, the purity of areaction intermediate is improved without a complex purification process, and the chiral purity of the final product trans-menthyl-2, 8-diene-1-ol is further improved.

Description

technical field [0001] The invention belongs to the technical field of preparation of trans-menthyl-2,8-dien-1-ol, and specifically relates to a synthesis process of trans-menthyl-2,8-dien-1-ol. Background technique [0002] Cannabidiol (CBD for short) is the main chemical component in the medicinal plant cannabis. It is extracted from the female cannabis plant and is a non-addictive component in cannabis. It has anti-spasmodic, anti-anxiety, anti-inflammatory, and pain-relieving pharmacological effects. [0003] CBD can not only help control the consumption of GABA neurotransmitter, suppress brain excitation, reduce seizures, but also help improve the efficacy of other anti-epileptic drugs. It can even effectively eliminate the hallucinogenic effect of tetrahydrocannabinol (THC) on the human body, known as the "anti-marijuana compound". [0004] Clinical studies have shown that cannabidiol has a significant effect on the treatment of Lennox-Gastaut syndrome and Dravet synd...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/00C07C35/18C07C391/02C12P17/02
Inventor 陈剑戈李斌峰张喜通
Owner JIANGSU JIMING PHARMA TECH
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