dictyopterene D | 29837-20-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: dictyopterene D
• 英文别名: (1R,2S)-1-ethenyl-2-[(1E,3Z)-hexa-1,3-dienyl]cyclopropane
• CAS: 29837-20-5；33967-69-0；50265-44-6；50265-46-8；50265-58-2；69575-73-1；69575-74-2；74709-22-1；75044-23-4；77210-41-4；77255-13-1；99438-20-7；99438-21-8；103833-89-2
• 化学式: C₁₁H₁₆
• 分子量: 148.248
• InChiKey: IUJUNEVKAIOLIM-WWYZZQEXSA-N

物化性质

• 沸点：
  197.8±15.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  dictyopterene D 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：

  2,4-戊二烯酸 在 lithium aluminium tetrahydride 、 sodium acetate 、 sodium hexamethyldisilazane 、 pyridinium chlorochromate 作用下， 以 乙醚 、 氘代氯仿 、 二氯甲烷 、 二氯甲烷-D2 为溶剂， 反应 78.5h， 生成 dictyopterene D
  参考文献：
  名称：

  Facile synthesis of fucoserratene and the (.+-.)-dictyopterenes B, D, and D' (= ectocarpene): constituents of marine brown algae

  摘要：

  DOI：

  10.1021/ja00539a024

文献信息

• Facile synthesis of fucoserratene and the (.+-.)-dictyopterenes B, D, and D' (= ectocarpene): constituents of marine brown algae
  作者：Manfred P. Schneider、Michael Goldbach

  DOI：10.1021/ja00539a024

  日期：1980.9
• 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.