ドデカヒドロ-3a,6,6,9a-テトラメチルナフト[2,1-b]フラン

ドデカヒドロ-3a,6,6,9a-テトラメチルナフト[2,1-b]フラン 化学特性,用途語,生産方法

• 化学的特性

  3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan is a crystalline autoxidation product of ambrein with a typical ambergris odor. It is prepared from (?)-sclareol, a diterpene alcohol obtained from extraction of clary sage plants. Oxidative degradation to a lactone (“sclareolide”), hydrogenation of the latter to the corresponding diol, and dehydration yield the title compound.

• 天然物の起源

  Reported found in clary sage oil.

• 製造方法

  Racemic sclareolide can be prepared by cyclization of homofarnesic acid in the presence of SnCl4 as a catalyst . Pure diastereomers are obtained by acid cyclization of (E)- and (Z)-4-methyl-6-(2,6,6-trimethylcyclohex-l(2)-enyl)-3- hexen-1-ol, prepared from 2-methyl-4-(2,6,6-trimethylcyclohex-l(2)-enyl)-2- butenal [394]. If the racemic sclareolide mixture is resolved into its enantiomers, the (–)-oxide may also be obtained by a totally synthetic route

• 製品名

  Compound starting from natural sclareol: Ambermore, Ambermore-DL, Ambermore-EX (Aromor), Ambrox® Super (Firmenich), Ambroxan® (Kao), Ambroxide (Symrise); compound starting from homofarnesic acid derivatives: Ambrox® DL (Firmenich); compound starting from 2-methyl- 4-(2,6,6-trimethylcyclohex-l(2)enyl)-2-butenal: Cetalox® (Firmenich), Cetalor (Aromor).

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