Method for synthesizing (E,E) Geranyl linalool

A kind of technology of geranyl linalool and synthesis method, which is applied in the field of synthesis, can solve problems such as lack of practical application value

Inactive Publication Date: 2007-11-14
CHENGDU UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Recently, Svatos synthesized (3R)- and (3S)-geranyllinalool from geranyl bromide and L-configuration or D-configuration citramalic acid through 7 steps, but the method used a large amount of cuprous cyanide , dic

Method used

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  • Method for synthesizing (E,E) Geranyl linalool
  • Method for synthesizing (E,E) Geranyl linalool
  • Method for synthesizing (E,E) Geranyl linalool

Examples

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Embodiment 1

[0030] 1) Synthesis of (E)-tertiary nerolidol tetrahydropyranyl ether

[0031]

[0032] (E)-Nerolidol (20.0g, 90mmol) and PPTS (1.58g, 3mmol) were added to dry dichloromethane (90mL), and dihydropyran (10.10g, 120mmol) was added dropwise under stirring After the dropwise addition, continue to stir overnight at room temperature, pour into a separatory funnel, add water to shake, let stand, separate the organic phase, extract the aqueous phase with dichloromethane (60mL) three times, combine the organic phases, and use anhydrous magnesium sulfate for the organic phase Dry and concentrate under reduced pressure to remove the solvent with a yield of 97%. IR and 1H NMR spectra showed that the structure of the product was correct.

[0033] 2) (E, E)-12-hydroxynerolidol tetrahydropyranyl ether

[0034]

[0035] SeO2 (0.666g, 6mmol) and 75% t-BuOOH (7.2g, 60mmol) were dissolved in 30mL of CH2Cl2, slowly added dropwise with CH2Cl2 solution (40mL) of geraniol tetrahydropyranyl e...

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Abstract

This invention relates to synthetic method of a ( E, E) - geranyl linalool. The invention takes (E) - nerolidol as raw material. The hydroxyl is shield by dihydropyrane, gain ( E) - nerolidol tetrahydropyrane aether; selenium dioxide and teri-butyl hydroperoxide selectively oxidize the anti-form methyl of ( E) - nerolidol tetrahydropyrane aether to gain anti-form allyl position hydroxylated oxidative product ( E, E) - 12 - hydroxy nerolidol tetrahydropyrane aether, transit halogenating reaction to gain ( E, E) - 12 - halogeno- nerolidol tetrahydropyrane aether, then take reaction with isopropyl methyl ketone that is selectively divested one proton by diisopropyl amido lithium, generate ( 6E, 10E) - 2, 6, 10, 14 - tetramethyl - 14 - ( tetrahydropyrane - 2 - oxygen) -16 - 6, 10, 15 - triene - 3 - ketone, use sodium borohydride to reduce to gain ( 6E, 10E) - 2, 6, 10, 14 - tetramethyl - 14 - ( tetrahydropyrane - 2 - oxygen) -16 - 6, 10, 15 - triene - 3 - alcohol, takes reaction with sulfonyl chloride or sulphonic acid ester with alkali presence to gain ( 6E, 10E) - 2, 6, 10, 14 - tetramethyl - 14 - ( tetrahydropyrane - 2 oxygen) -16 - 6, 10, 15 - triene - 3 - alcoholic sulphonic acid ester, then divide sulphonic acid ester group under base catalysis to gain ( E, E) - geranyl linalool tetrahydropyrane aether, and by deprotection to gain ( E, E) - geranyl linalool. ˕For the configuration of ( E) - nerolidol 3 position tertiary carbon is not influenced in the course of reaction, if use ( E) - nerolidol that has optical activity as raw material, should gain optical active ( E, E) - geranyl linalool. ((E, E)-geranyl linalool can replace Teprenone and such type medicament intermediate, natural product intermediate, insect pheromone and spice etc.

Description

technical field [0001] The invention relates to a synthesis method of (E, E)-geranyl linalool. Background technique [0002] (E,E)-Geranyllinalool ((E,E)-Geranyllinalool, (6E,10E)-3,7,11,15-Tetramethyl-hexadeca-1,6,10,14-tetraen-3-ol ) is a straight-chain diterpenoid, and its molecular structural formula is: [0003] [0004] (E,E)-Geranyllinalool is an important intermediate of chain diterpenoids and natural products, a bioactive compound and a fragrance-fixing component of spices. [0005] (E, E)-geranyllinalool reacts with methyl acetoacetate under the catalysis of aluminum isopropoxide to obtain the gastric mucosal protective agent teprenone, which will be the most convenient synthesis method for teprenone. Geranyl linalool undergoes a one-step rearrangement to obtain geranyl nerolidol. (E, E)-geranyllinalool can also be used as insect pheromone and insect natural insecticide. It is also a fragrance-fixing component of high-end fragrances. Therefore, (E, E)-geran...

Claims

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Application Information

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IPC IPC(8): C07C33/02C07C29/44C07C29/00
Inventor 曾庆乐
Owner CHENGDU UNIVERSITY OF TECHNOLOGY
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