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Germacrone alcoholization and biological resolution method

A biological and rhododendron technology, applied in the field of rhododendron ketolization and bio-separation, can solve problems such as unseen and unseen

Inactive Publication Date: 2017-02-08
王际菊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, there have been no reports on the synthesis of ​3,6-diethyl-2,5-dimethylcyclohex-2-en-1-ol, nor have there been reports on the two optically different Construct R​-3,6-diethyl-2,5-dimethylcyclohex-2-en-1-ol and S​-3,6-diethyl-2,5-dimethylcyclo Report on the Synthesis and Resolution of Hex-2-en-1-ol

Method used

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  • Germacrone alcoholization and biological resolution method

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Embodiment 1

[0012] 1) At 0°C, add 250ml of anhydrous methanol and 18g of rhododendron into a single-necked flask. After stirring for 15 minutes, add 12g of sodium borohydride. After feeding, seal the flask with a balloon and keep it at 0°C for 3 hours. TLC detects Rhododendron The ketone reaction is complete, stop the reaction; quench sodium borohydride with dilute hydrochloric acid solution until no more bubbles emerge, distill off methanol and extract with 100ml dichloromethane three times, combine dichloromethane, dry and concentrate to obtain -3 , 17.8 g of 6-diethyl-2,5-dimethylcyclohex-2-en-1-ol, the yield was 98.0%.

[0013] 2) Add 60ml of toluene and 9.1g of ​3,6-diethyl-2,5-dimethylcyclohex-2-en-1-ol in a constant temperature shaker with a 200ml blue cap bottle as the reaction vessel , 11g of p-chlorophenol acetate, 0.6g of porcine pancreatic lipase PPL, and 1.5g of acid resin D006. After feeding, the temperature was raised to 45°C for reaction. After 12 hours, ​-3,6-diethyl-2, ...

Embodiment 2

[0019] 1) At 0°C, add 1000ml of anhydrous methanol and 180g of rhododendron to a single-necked flask, stir for 20 minutes, then add 150g of sodium borohydride. After feeding, seal the flask with a balloon and keep it at 0°C for 4 hours. TLC detects rhododendron The ketone reaction is complete, stop the reaction; dilute the sodium borohydride with hydrochloric acid solution until there are no more bubbles, distill the methanol and extract with 300ml ethyl acetate three times, combine the ethyl acetate, dry and concentrate to get -3 , 178.9 g of 6-diethyl-2,5-dimethylcyclohex-2-en-1-ol, the yield was 98.3%.

[0020] 2) In a constant temperature shaker, with a 1000ml blue cap bottle as a reaction vessel, add 700ml of toluene, 91g of 3,6-diethyl-2,5-dimethylcyclohex-2-en-1-ol, 110g p-Chlorophenol acetate, 9g porcine pancreatic lipase PPL, 18g acid resin D006, after feeding, raise the temperature to 40°C for reaction, after 12 hours, detect​-3,6-diethyl-2,5-dimethyl Cyclohexa-2-en...

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Abstract

The invention discloses a germacrone alcoholization and biological resolution method. The method comprises the following steps: by taking germacrone extracted from cedar branches and leaves as a raw material, carrying out reduction with sodium borohydride to obtain a compound II, carrying out enzymatic kinetic resolution reaction on the compound II to obtain a compound III and a compound IV, or carrying out dynamic kinetic resolution to obtain a compound III of which the yield is more than 90%, and hydrolyzing the compound III to obtain a compound V. According to the invention, a latent chiral ketone group in germacrone is further changed to a chiral hydroxyl center so as to carry out further resolution. The method disclosed by the invention has the characteristics of simple operation, high product yield, good optical purity and the like.

Description

technical field [0001] The present invention relates to a method for the reductive alcoholization of latent chiral ketones and the biological resolution of alcohols, in particular to the preparation of 3,6-diethyl-2,5-dimethylcyclohexyl-2- En-1-ols were further subjected to an enzyme-catalyzed dynamic kinetic resolution method. Background technique [0002] Rhododendron has a warm honey-like aroma with notes of dried flowers. Addition of 2-3% will produce the effect of ionone. When added to 10%, it can reconcile floral and woody notes. Especially suitable For honey-sweet floral fragrance formula. At the same time, it is also a latent chiral ketone compound, which can be further reduced and alcoholized to become a chiral alcohol compound with a chiral center. [0003] However, there have been no reports on the synthesis of ​3,6-diethyl-2,5-dimethylcyclohex-2-en-1-ol, nor have there been reports on the two optically different Construct R​-3,6-diethyl-2,5-dimethylcyclohex-2-...

Claims

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Application Information

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IPC IPC(8): C07C29/143C07C27/02C07C29/92C07C35/18C12P7/62C12P41/00
CPCC07C29/143C07C29/095C07C29/92C12P7/62C12P41/005C07C35/18
Inventor 王际菊
Owner 王际菊
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