1-(7-bromobicyclo[4.1.0]hept-3-en-7-yl)cyclopent-2-en-1-ol | 270595-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(7-bromobicyclo[4.1.0]hept-3-en-7-yl)cyclopent-2-en-1-ol
• 英文别名: 1-(7-Bromo-7-bicyclo[4.1.0]hept-3-enyl)cyclopent-2-en-1-ol
• CAS: 270595-31-8
• 化学式: C₁₂H₁₅BrO
• 分子量: 255.155
• InChiKey: XMLSSNDMKAJLGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(7-bromobicyclo[4.1.0]hept-3-en-7-yl)cyclopent-2-en-1-ol 在 aluminum oxide 、 对甲苯磺酸 作用下， 以 乙醚 、 正戊烷 、 苯 为溶剂， 反应 3.0h， 生成 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：

  2-环戊烯酮 、 7,7-二溴-二环[4.1.0]庚-3-烯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以90%的产率得到1-(7-bromobicyclo[4.1.0]hept-3-en-7-yl)cyclopent-2-en-1-ol
  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

文献信息

• ——
  作者：Xiaoming Li、Markus Neuenschwander

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

  日期：2000.3.15

  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.