8-exo-methoxybicyclo[4.2.0]oct-2-ene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-exo-methoxybicyclo[4.2.0]oct-2-ene
• 英文别名: (1R,6S,8S)-8-methoxybicyclo[4.2.0]oct-2-ene
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: IZIQVQGYJCFVMR-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-exo-methoxybicyclo[4.2.0]oct-2-ene 生成 1,3-环己二烯
  参考文献：
  名称：

  Effect of a Methoxy Substituent on the Vinylcyclobutane Carbon Migration

  摘要：

  Over the temperature range 250-300 degrees C, 8-exo-methoxybicyclo[4.2.0]oct-2-ene (1a) undergoes a [1,3] sigmatropic rearrangement to 5-exo- and 5-endo-methoxybicyclo[2.2.2]oct-2-enes, 2a and 2b, respectively, with a clear preference for the si product: si/sr = 3.2. Both 1a and its 8-endo epimer 1b experience appreciable epimerization and fragmentation. A long-lived intermediate with weakly interacting diradical centers, one of which is stabilized by a methoxy substituent, can account for all such observations.

  DOI：

  10.1021/jo0621017
• 作为产物：
  描述：

  8-methoxybicyclo[4.2.0]oct-2-en-7-one 在 potassium tert-butylate 、 肼 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 8-exo-methoxybicyclo[4.2.0]oct-2-ene
  参考文献：
  名称：

  Effect of a Methoxy Substituent on the Vinylcyclobutane Carbon Migration

  摘要：

  Over the temperature range 250-300 degrees C, 8-exo-methoxybicyclo[4.2.0]oct-2-ene (1a) undergoes a [1,3] sigmatropic rearrangement to 5-exo- and 5-endo-methoxybicyclo[2.2.2]oct-2-enes, 2a and 2b, respectively, with a clear preference for the si product: si/sr = 3.2. Both 1a and its 8-endo epimer 1b experience appreciable epimerization and fragmentation. A long-lived intermediate with weakly interacting diradical centers, one of which is stabilized by a methoxy substituent, can account for all such observations.

  DOI：

  10.1021/jo0621017

文献信息

• Effect of a Methoxy Substituent on the Vinylcyclobutane Carbon Migration
  作者：Phyllis A. Leber、Celina C. Lasota、Neil A. Strotman、Gloria S. Yen

  DOI：10.1021/jo0621017

  日期：2007.2.1

  Over the temperature range 250-300 degrees C, 8-exo-methoxybicyclo[4.2.0]oct-2-ene (1a) undergoes a [1,3] sigmatropic rearrangement to 5-exo- and 5-endo-methoxybicyclo[2.2.2]oct-2-enes, 2a and 2b, respectively, with a clear preference for the si product: si/sr = 3.2. Both 1a and its 8-endo epimer 1b experience appreciable epimerization and fragmentation. A long-lived intermediate with weakly interacting diradical centers, one of which is stabilized by a methoxy substituent, can account for all such observations.