8-phenyl-8-chloro-2-oxa-cis-bicyclo<4.2.0>octan-7-one | 131376-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 8-phenyl-8-chloro-2-oxa-cis-bicyclo<4.2.0>octan-7-one
• 英文别名: 8-phenyl-8-chloro-2-oxa-cis-bicyclo[4.2.0]octan-7-one；(1S,6R,8R)-8-chloro-8-phenyl-2-oxabicyclo[4.2.0]octan-7-one
• CAS: 131376-04-0；139757-89-4；150851-54-0
• 化学式: C₁₃H₁₃ClO₂
• 分子量: 236.698
• InChiKey: RKZXLFDWUFYWSF-DRZSPHRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-phenyl-8-chloro-2-oxa-cis-bicyclo<4.2.0>octan-7-one 在 水 、 lithium perchlorate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以25%的产率得到4-(3''-Hydroxypropyl)-2,5-diphenyl-5-(3'-hydroxy-3'-carboxytetrahydropyran-2'-yl)-2-cyclopenten-1-one
  参考文献：
  名称：

  Stereochemistry. 83. Unusual rearrangements in cage compounds due to proximity effects

  摘要：

  The strained keto diol 5 underwent an unexpected rearrangement in the presence of H2O-TEA-CH3CN at 20-degrees-C to afford two isomeric products 6 and 7. The latter two compounds undergo further conversion to carboxy keto diol 8. The structures of 6-8 were elucidated by heterero COSY experiments and in the case of 6 by X-ray diffraction. The transformation of 5 to 6 and 7 is interpreted as involving an unusual retroaddition of a benzylic anion to a cyclobutanone 5 --> 10. This is facilitated by subsequent readdition of this anion to another proximally located ketone with formation of a cyclopropanol 11, which is immediately converted to 6 and 7.

  DOI：

  10.1021/jo00073a031
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 DL-2-氯-2-苯基乙酰氯 在 TEA 作用下， 反应 1.0h， 以75%的产率得到8-phenyl-8-chloro-2-oxa-cis-bicyclo<4.2.0>octan-7-one
  参考文献：
  名称：

  Proximity effects in fused cyclobutanones. Facile formation of cage systems

  摘要：

  Chlorbicyclooctanone 3 on reaction with H2O-Et3N in acetonitrile at 20-degrees-C produced in high yield four complex dimeric compounds 4-7. The novel structures produced by C-C bond formation between tertiary centers were revealed by NMR and X-ray diffraction. Pathways leading from 4 or its diastereomer 14 to cage compounds 5-7 indicate the importance of proximity effects in these transformations.

  DOI：

  10.1021/jo00034a045

表征谱图