8-chloro-8-methylbicyclo[4.2.0]oct-2-en-7-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-chloro-8-methylbicyclo[4.2.0]oct-2-en-7-one
• 英文别名: (1R,6S)-8-chloro-8-methylbicyclo[4.2.0]oct-2-en-7-one
• 化学式: C₉H₁₁ClO
• 分子量: 170.639
• InChiKey: VLZGLBMWFFQNQR-PMDVUHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-chloro-8-methylbicyclo[4.2.0]oct-2-en-7-one 在 四甲基乙二胺 、 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 生成 8-exo-Methylbicyclo<4.2.0>oct-2-en-7-one 、 8-endo-Methylbicyclo<4.2.0>oct-2-en-7-one
  参考文献：
  名称：

  Thermal Reactions of 8-Methylbicyclo[4.2.0]oct-2-enes:  Competitive Diradical-Mediated [1,3] Sigmatropic, Stereomutation, and Fragmentation Processes

  摘要：

  At 275 degrees C, 8-exo-methylbicyclo[4.2.0]oct-2-ene (1a) undergoes a [1,31 sigmatropic rearrangement to 5-methylbicyclo[2.2.2]oct-2-enes, of which the orbital symmetry-allowed si product is only marginally favored over the forbidden sr product; that is, si/sr is 2.4. Accompanying the [1,31 shift are significant amounts of epimerization and fragmentation. The 8-endo epimer 1b, which yields no [1,31 product, experiences primarily direct fragmentation and secondarily epimerization. A diradical intermediate can account for all such observations.

  DOI：

  10.1021/jo051505g
• 作为产物：
  描述：

  2-氯丙酰氯 、 1,3-环己二烯 在 三乙胺 作用下， 以 氯仿 为溶剂， 以63%的产率得到8-chloro-8-methylbicyclo[4.2.0]oct-2-en-7-one
  参考文献：
  名称：

  Thermal Reactions of 8-Methylbicyclo[4.2.0]oct-2-enes:  Competitive Diradical-Mediated [1,3] Sigmatropic, Stereomutation, and Fragmentation Processes

  摘要：

  At 275 degrees C, 8-exo-methylbicyclo[4.2.0]oct-2-ene (1a) undergoes a [1,31 sigmatropic rearrangement to 5-methylbicyclo[2.2.2]oct-2-enes, of which the orbital symmetry-allowed si product is only marginally favored over the forbidden sr product; that is, si/sr is 2.4. Accompanying the [1,31 shift are significant amounts of epimerization and fragmentation. The 8-endo epimer 1b, which yields no [1,31 product, experiences primarily direct fragmentation and secondarily epimerization. A diradical intermediate can account for all such observations.

  DOI：

  10.1021/jo051505g

文献信息

• US4927963A
  申请人：——

  公开号：US4927963A

  公开（公告）日：1990-05-22