7-bromo-7-(cyclopenta-1,4-dienyl)bicyclo[4.1.0]hept-3-ene | 270595-32-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 7-bromo-7-(cyclopenta-1,4-dienyl)bicyclo[4.1.0]hept-3-ene
• 英文别名: 7-Bromo-7-cyclopenta-1,4-dien-1-ylbicyclo[4.1.0]hept-3-ene
• CAS: 270595-32-9
• 化学式: C₁₂H₁₃Br
• 分子量: 237.139
• InChiKey: WLXULHQCKRHOHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  7-bromo-7-(cyclopenta-1,4-dienyl)bicyclo[4.1.0]hept-3-ene 在 aluminum oxide 作用下， 以 乙醚 、 正戊烷 为溶剂， 以89%的产率得到7-(cyclopenta-2,4-dienylidene)bicyclo[4.1.0]hept-3-ene
  参考文献：
  名称：

  摘要：

  A new general pathway to the parent cross-conjugated hydrocarbons heptafulvene (1) (Scheme 3), sesquifulvalene (2) (Scheme 4), and heptafulvalene (3) (Scheme 5 has been explored, starting with essay available 7,7-dibromobicyclo[4.1.0]hept-3-ene (13). Promising precursors have been synthesized by halo/lithio exchange of 1,1-dibromocyclopropane 13 --> 14, followed by methylation (--> 1), cyclopentadienylation (-->2) and CuCI2-induced 'carbene dimerization' (--> 3) of the carbenoid 14 So far the main obstacle of all three sequences (cf: Schemes 3, 4, and 5) is the final base-induced dehydrobromination of precursors 17, 24 and 27, which should be investigated in more detail.

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<562::aid-hlca562>3.0.co;2-m
• 作为产物：
  描述：

  1-(7-bromobicyclo[4.1.0]hept-3-en-7-yl)cyclopent-2-en-1-ol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.0h， 以91.5%的产率得到7-bromo-7-(cyclopenta-1,4-dienyl)bicyclo[4.1.0]hept-3-ene
  参考文献：
  名称：

  摘要：

  A new general pathway to the parent cross-conjugated hydrocarbons heptafulvene (1) (Scheme 3), sesquifulvalene (2) (Scheme 4), and heptafulvalene (3) (Scheme 5 has been explored, starting with essay available 7,7-dibromobicyclo[4.1.0]hept-3-ene (13). Promising precursors have been synthesized by halo/lithio exchange of 1,1-dibromocyclopropane 13 --> 14, followed by methylation (--> 1), cyclopentadienylation (-->2) and CuCI2-induced 'carbene dimerization' (--> 3) of the carbenoid 14 So far the main obstacle of all three sequences (cf: Schemes 3, 4, and 5) is the final base-induced dehydrobromination of precursors 17, 24 and 27, which should be investigated in more detail.

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<562::aid-hlca562>3.0.co;2-m