(2E/Z)-2,3,4,4-tetramethylpent-2-enoic acid | 357650-22-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E/Z)-2,3,4,4-tetramethylpent-2-enoic acid
• 英文别名: 2,3,4,4-Tetramethylpent-2-enoic acid；2,3,4,4-tetramethylpent-2-enoic acid
• CAS: 357650-22-7
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: MRVKYSXMRPYSKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-propenyl lithium 、 (2E/Z)-2,3,4,4-tetramethylpent-2-enoic acid 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 以8%的产率得到(2E,5E)-5,6,7,7-tetramethylocta-2,5-dien-4-one
  参考文献：
  名称：

  5,6,7-Trimethylocta-2,5-dien-4-one − A Suspected Odorant with Surprising Olfactory Properties

  摘要：

  5,6,7-Trimethylocta-2,5-dien-4-one (3) was suspected of being a trace component smelling of damascone in a crude complex reaction product. Although this trace component eventually turned out to be the constitutional isomer 2-methyl-3-isopropylhepta-2,5-dien-4-one (4), the title compound 3 was found to possess even superior fruity, rosy odor characteristics, reminiscent of apples, plums, raisins and other dried fruits, and these odor characteristics are, surprisingly, due mainly to its (5Z)-isomer. The synthesis of 3 commenced with the preparation of 1-ethoxyprop-1-yne (11) from 2-chloro-1,1-diethoxyethane (9). Borontrifluoride-catalyzed addition of methyl isopropyl ketone (10) to 11 provided ethyl 2,3,4-trimethylpent-2-enoate (8), which was transformed into the target molecule 3 by Grignard reaction with propen-1-ylmagnesium bromide and in situ enolization. Further derivatives 13-16 provide more insight into the structure-odor correlation of damascone-type odorants, and the use of 3 in perfumery is illustrated by a composition formula of a demonstration perfume.

  DOI：

  10.1002/1099-0690(200106)2001:12<2363::aid-ejoc2363>3.0.co;2-e
• 作为产物：
  描述：

  (2E/Z)-ethyl 2,3,4,4-tetramethylpent-2-enoate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以70%的产率得到(2E/Z)-2,3,4,4-tetramethylpent-2-enoic acid
  参考文献：
  名称：

  5,6,7-Trimethylocta-2,5-dien-4-one − A Suspected Odorant with Surprising Olfactory Properties

  摘要：

  5,6,7-Trimethylocta-2,5-dien-4-one (3) was suspected of being a trace component smelling of damascone in a crude complex reaction product. Although this trace component eventually turned out to be the constitutional isomer 2-methyl-3-isopropylhepta-2,5-dien-4-one (4), the title compound 3 was found to possess even superior fruity, rosy odor characteristics, reminiscent of apples, plums, raisins and other dried fruits, and these odor characteristics are, surprisingly, due mainly to its (5Z)-isomer. The synthesis of 3 commenced with the preparation of 1-ethoxyprop-1-yne (11) from 2-chloro-1,1-diethoxyethane (9). Borontrifluoride-catalyzed addition of methyl isopropyl ketone (10) to 11 provided ethyl 2,3,4-trimethylpent-2-enoate (8), which was transformed into the target molecule 3 by Grignard reaction with propen-1-ylmagnesium bromide and in situ enolization. Further derivatives 13-16 provide more insight into the structure-odor correlation of damascone-type odorants, and the use of 3 in perfumery is illustrated by a composition formula of a demonstration perfume.

  DOI：

  10.1002/1099-0690(200106)2001:12<2363::aid-ejoc2363>3.0.co;2-e

文献信息

• 5,6,7-Trimethylocta-2,5-dien-4-one − A Suspected Odorant with Surprising Olfactory Properties
  作者：Philip Kraft、Caroline Denis、Walter Eichenberger

  DOI：10.1002/1099-0690(200106)2001:12<2363::aid-ejoc2363>3.0.co;2-e

  日期：2001.6

  5,6,7-Trimethylocta-2,5-dien-4-one (3) was suspected of being a trace component smelling of damascone in a crude complex reaction product. Although this trace component eventually turned out to be the constitutional isomer 2-methyl-3-isopropylhepta-2,5-dien-4-one (4), the title compound 3 was found to possess even superior fruity, rosy odor characteristics, reminiscent of apples, plums, raisins and other dried fruits, and these odor characteristics are, surprisingly, due mainly to its (5Z)-isomer. The synthesis of 3 commenced with the preparation of 1-ethoxyprop-1-yne (11) from 2-chloro-1,1-diethoxyethane (9). Borontrifluoride-catalyzed addition of methyl isopropyl ketone (10) to 11 provided ethyl 2,3,4-trimethylpent-2-enoate (8), which was transformed into the target molecule 3 by Grignard reaction with propen-1-ylmagnesium bromide and in situ enolization. Further derivatives 13-16 provide more insight into the structure-odor correlation of damascone-type odorants, and the use of 3 in perfumery is illustrated by a composition formula of a demonstration perfume.