(6R,9R)-γ-ionol acetate | 315208-24-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (6R,9R)-γ-ionol acetate
• 英文别名: [(E,2R)-4-[(1R)-2,2-dimethyl-6-methylidenecyclohexyl]but-3-en-2-yl] acetate
• CAS: 315208-24-3
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: WCACCDKNSQRHFQ-JWEWWIMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6R,9R)-γ-ionol acetate 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 水 、 三正丁基氢锡 、 氯化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 (-)-γ-dihydroionone
  参考文献：
  名称：

  摘要：

  The synthesis of enantiometically pure (+)- and (-)-gamma -ionone 3 is reported. The first step in the synthesis is the diastereoisomeric enrichment of 4-nitrobenzoate derivatives or racemic gamma -ionol 12. The enantioselective lipase-mediated kinetic acetylation of gamma -ionol 13b afforded the acetate 14 and the alcohol 15, which are suitable precursors of the desired products (-)- and (+)-3, respectively. The olfactory evaluation of the gamma -ionone isomers shows a great difference between the two enantiomers both in fragrance response and in detection threshold. The selective reduction of (-)-3 and (+)-3 to the gamma -dihydroionones (-)-(R)-16 and (+)-(S)-17, respectively, allowed us to assign unambiguously the absolute configuration of the gamma -ionones.

  DOI：

  10.1002/1522-2675(20001004)83:10<2761::aid-hlca2761>3.0.co;2-9
• 作为产物：
  描述：

  γ-cyclocitral 在 吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 Lipase PS (Pseudomonas cepacia) 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 82.0h， 生成 (6R,9R)-γ-ionol acetate
  参考文献：
  名称：

  摘要：

  The synthesis of enantiometically pure (+)- and (-)-gamma -ionone 3 is reported. The first step in the synthesis is the diastereoisomeric enrichment of 4-nitrobenzoate derivatives or racemic gamma -ionol 12. The enantioselective lipase-mediated kinetic acetylation of gamma -ionol 13b afforded the acetate 14 and the alcohol 15, which are suitable precursors of the desired products (-)- and (+)-3, respectively. The olfactory evaluation of the gamma -ionone isomers shows a great difference between the two enantiomers both in fragrance response and in detection threshold. The selective reduction of (-)-3 and (+)-3 to the gamma -dihydroionones (-)-(R)-16 and (+)-(S)-17, respectively, allowed us to assign unambiguously the absolute configuration of the gamma -ionones.

  DOI：

  10.1002/1522-2675(20001004)83:10<2761::aid-hlca2761>3.0.co;2-9

文献信息

• ——
  作者：Claudio Fuganti、Stefano Serra、Alessandro Zenoni

  DOI：10.1002/1522-2675(20001004)83:10<2761::aid-hlca2761>3.0.co;2-9

  日期：2000.10.4

  The synthesis of enantiometically pure (+)- and (-)-gamma -ionone 3 is reported. The first step in the synthesis is the diastereoisomeric enrichment of 4-nitrobenzoate derivatives or racemic gamma -ionol 12. The enantioselective lipase-mediated kinetic acetylation of gamma -ionol 13b afforded the acetate 14 and the alcohol 15, which are suitable precursors of the desired products (-)- and (+)-3, respectively. The olfactory evaluation of the gamma -ionone isomers shows a great difference between the two enantiomers both in fragrance response and in detection threshold. The selective reduction of (-)-3 and (+)-3 to the gamma -dihydroionones (-)-(R)-16 and (+)-(S)-17, respectively, allowed us to assign unambiguously the absolute configuration of the gamma -ionones.