endo-7-Chlor-exo-7-carboxynorcaran | 18688-20-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: endo-7-Chlor-exo-7-carboxynorcaran
• CAS: 18688-20-5
• 化学式: C₈H₁₁ClO₂
• 分子量: 174.627
• InChiKey: WFELEHIEGFJXPC-UQWHLADISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  endo-7-Chlor-exo-7-carboxynorcaran 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以2.71 g的产率得到methyl endo-7-chlorobicyclo[4.1.0]heptane-7-carboxylate
  参考文献：
  名称：

  SmI₂-Promoted Reformatsky-Type Reaction and Acylation of Alkyl 1-Chlorocyclopropanecarboxylates

  摘要：

  In the presence of HMPA in THF, highly stereoselective Sml(2)-promoted substitutions of alkyl 1-chlorocyclopropanecarboxylates 1 using various ketones, aldehydes (Reformatsky-type reaction), and acyl chlorides (acylation) proceeded to give trans-adducts (2 or 5) in good to high yield with excellent trans-stereoselectivity (trans-add/cis-add = > 99/1). The Reformatsky-type reaction of 1 with aldehydes and unsymmetrical ketones proceeded with moderate diastereoselectivity (re-face-adduct/si-face-adduct = 60/40-75/25).

  DOI：

  10.1021/ol8022038
• 作为产物：
  描述：

  endo-7-chlorobicyclo[4.1.0]heptane-7-carbaldehyde 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 endo-7-Chlor-exo-7-carboxynorcaran
  参考文献：
  名称：

  SmI₂-Promoted Reformatsky-Type Reaction and Acylation of Alkyl 1-Chlorocyclopropanecarboxylates

  摘要：

  In the presence of HMPA in THF, highly stereoselective Sml(2)-promoted substitutions of alkyl 1-chlorocyclopropanecarboxylates 1 using various ketones, aldehydes (Reformatsky-type reaction), and acyl chlorides (acylation) proceeded to give trans-adducts (2 or 5) in good to high yield with excellent trans-stereoselectivity (trans-add/cis-add = > 99/1). The Reformatsky-type reaction of 1 with aldehydes and unsymmetrical ketones proceeded with moderate diastereoselectivity (re-face-adduct/si-face-adduct = 60/40-75/25).

  DOI：

  10.1021/ol8022038