6-vinylcyclohepta-1,4-diene | 92340-53-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 6-vinylcyclohepta-1,4-diene
• 英文别名: 6-Ethenylcyclohepta-1,4-diene
• CAS: 92340-53-9
• 化学式: C₉H₁₂
• 分子量: 120.194
• InChiKey: WGZPMONOKKDYNV-UHFFFAOYSA-N

物化性质

• 沸点：
  161.4±40.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (1S,2R)-1-((E)-Buta-1,3-dienyl)-2-vinyl-cyclopropane 生成 6-vinylcyclohepta-1,4-diene
  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

• Novel C₉and C₁₁Hydrocarbons from the Brown Alga<i>Cutleria multifida</i>; Sigmatropic and Electrocyclic Reactions in Nature. Part VI
  作者：Jürgen Keitel、Iris Fischer-Lui、Wilhelm Boland、Dieter G. Müller

  DOI：10.1002/hlca.19900730806

  日期：1990.12.12

  the marine brown alga Cutleria multifida produces trace amounts of the C9H12 hydrocarbon 7-melhylcycloocta-1,3,5-triene (8) and its valence tautomer 7-methylbicyclo[4.2.0]octa-2,4-diene, A second novel C9H12 hydrocarbon is 6-vinyicyclo-hepta-1,4-diene (9), a lower homologue of ectocarpene (5). Among the C11H16 hydrocarbons, 7-((1E/Z)-prop-l-enyl)cycloocta-1,4-diene (10/11) is found for the first time

  除了已知的C 11 H 16烃多芬（4），uc蒽（2）和外果皮（5）外，海生褐藻多菌种还产生痕量的C 9 H 12烃7-甲基环辛基1,3， 5-三烯（8）及其价互变异构体7-甲基双环[4.2.0] octa-2,4-二烯，第二种新型C 9 H 12烃是6-乙烯基环庚-1,4-二烯（9），较低的外果皮同源物（5）。在C 11 H 16烃中，7-（（1 E /Ž） -丙-1-烯基）环辛-1,4-二烯（10 / 11）被发现首次。所有新产品的结构均已通过合成和光谱数据证实。新烃的生物合成8 - 11显然与这导致主要产物giffordene（途径7），（6小号）-ectocarpene（（6-小号） - 5），和（4 - [R，5 - [R ）-紫杉烯（（4 R，5 R）-2）。某些不耐热的初级产物的连续反应通过 电环闭合，3,3-σ重排或1,7σH移。
• KEITEL, JURGEN;FISCHER-LUI, IRIS;BOLAND, WILHELM;MULLER, DIETER G., HELV. CHIM. ACTA, 73,(1990) N, C. 2101-2112
  作者：KEITEL, JURGEN、FISCHER-LUI, IRIS、BOLAND, WILHELM、MULLER, DIETER G.

  DOI：——

  日期：——
• 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.