(1S,2S)-2-[(1E,3Z)-1,3-己二烯-1-基]环丙烷甲醛 | 197579-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 中文名称: (1S,2S)-2-[(1E,3Z)-1,3-己二烯-1-基]环丙烷甲醛
• 英文名称: Cyclopropanecarboxaldehyde, 2-(1,3-hexadienyl)-, [1S-[1alpha,2alpha(1E,3Z)]]-(9CI)
• 英文别名: (1S,2S)-2-[(1E,3Z)-hexa-1,3-dienyl]cyclopropane-1-carbaldehyde
• CAS: 197579-08-1
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: GVUBFZQUXOQYAR-HCXXOREESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-[(1E,3Z)-1,3-己二烯-1-基]环丙烷甲醛 在 sodium hydride 、 二甲基亚砜 作用下， 反应 0.05h， 生成 dictyopterene D'
  参考文献：
  名称：

  Pericyclic reactions in nature: Synthesis and Cope rearrangement of thermolabile bis-alkenylcyclopropanes from female gametes of marine brown algae (Phaeophyceae)

  摘要：

  The biosyntheses of the 6-substituted cyclohepta-1,4-dienes dictyotene (1), ectocarpene (2), desmarestene (3), vinylcycloheptadiene (4) and lamoxirene (5) involve a spontaneous Cope rearrangement of thermolabile bis-alkenylcyclopropane precursors like 16, 10, 26 and 30. The unstable precursors and the rearranged cycloheptadienes were synthesised from the chiral 2-iodovinylcyclopropane 12 using Pd-0 or Cu-1 catalysed approaches. Activation parameters of the Cope rearrangements were determined. Bioassays with pre-ectocarpene 10 established the thermolabile cyclopropane (1R,2R)-10, rather than the cyclohepta-1,4-diene(6S)-2, as the genuine pheromone of the brown alga Ectocarpus siliculosus. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00886-7
• 作为产物：
  描述：

  Acetic acid (1S,2S)-((1E,3Z)-2-hexa-1,3-dienyl)-cyclopropylmethyl ester 在 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 3.42h， 生成 (1S,2S)-2-[(1E,3Z)-1,3-己二烯-1-基]环丙烷甲醛
  参考文献：
  名称：

  Pericyclic reactions in nature: Synthesis and Cope rearrangement of thermolabile bis-alkenylcyclopropanes from female gametes of marine brown algae (Phaeophyceae)

  摘要：

  The biosyntheses of the 6-substituted cyclohepta-1,4-dienes dictyotene (1), ectocarpene (2), desmarestene (3), vinylcycloheptadiene (4) and lamoxirene (5) involve a spontaneous Cope rearrangement of thermolabile bis-alkenylcyclopropane precursors like 16, 10, 26 and 30. The unstable precursors and the rearranged cycloheptadienes were synthesised from the chiral 2-iodovinylcyclopropane 12 using Pd-0 or Cu-1 catalysed approaches. Activation parameters of the Cope rearrangements were determined. Bioassays with pre-ectocarpene 10 established the thermolabile cyclopropane (1R,2R)-10, rather than the cyclohepta-1,4-diene(6S)-2, as the genuine pheromone of the brown alga Ectocarpus siliculosus. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00886-7

文献信息

• Pericyclic reactions in nature: Synthesis and Cope rearrangement of thermolabile bis-alkenylcyclopropanes from female gametes of marine brown algae (Phaeophyceae)
  作者：Georg Pohnert、Wilhelm Boland

  DOI：10.1016/s0040-4020(97)00886-7

  日期：1997.10

  The biosyntheses of the 6-substituted cyclohepta-1,4-dienes dictyotene (1), ectocarpene (2), desmarestene (3), vinylcycloheptadiene (4) and lamoxirene (5) involve a spontaneous Cope rearrangement of thermolabile bis-alkenylcyclopropane precursors like 16, 10, 26 and 30. The unstable precursors and the rearranged cycloheptadienes were synthesised from the chiral 2-iodovinylcyclopropane 12 using Pd-0 or Cu-1 catalysed approaches. Activation parameters of the Cope rearrangements were determined. Bioassays with pre-ectocarpene 10 established the thermolabile cyclopropane (1R,2R)-10, rather than the cyclohepta-1,4-diene(6S)-2, as the genuine pheromone of the brown alga Ectocarpus siliculosus. (C) 1997 Elsevier Science Ltd.