(-)-(R)-γ-ionone | 24190-32-7

• 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: (-)-(R)-γ-ionone
• 英文别名: (-)-γ-ionone；γ-ionone；(+)-γ-Ionon；(-)-gamma-Ionone；(E)-4-[(1R)-2,2-dimethyl-6-methylidenecyclohexyl]but-3-en-2-one
• CAS: 24190-32-7
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: SFEOKXHPFMOVRM-GUOLPTJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  (-)-(R)-γ-ionone 在 bis-triphenylphosphine-palladium(II) chloride 水 、 三正丁基氢锡 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以72%的产率得到(-)-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：

  (6R,9R)-γ-ionol acetate 在 氢氧化钾 、 manganese(IV) oxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 4.0h， 以81%的产率得到(-)-(R)-γ-ionone
  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

• Oritani, Takayuki; Yamashita, Kyohei, Agricultural and Biological Chemistry, 1987, vol. 51, # 5, p. 1271 - 1276
  作者：Oritani, Takayuki、Yamashita, Kyohei

  DOI：——

  日期：——
• ——
  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.