trans-2-(5-Chloro-3-pentenyl)cyclopentanone | 152668-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2-(5-Chloro-3-pentenyl)cyclopentanone
• 英文别名: 2-[(E)-5-chloropent-3-enyl]cyclopentan-1-one
• CAS: 152668-07-0
• 化学式: C₁₀H₁₅ClO
• 分子量: 186.681
• InChiKey: BEXLMOVTDKXDAW-HNQUOIGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  trans-2-(5-Chloro-3-pentenyl)cyclopentanone 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以35%的产率得到trans-5-(5-Chloro-3-pentenyl)-5-pentanolide
  参考文献：
  名称：

  Intramolecular nucleophilic acyl substitution reactions of halo-substituted esters and lactones. New applications of organosamarium reagents

  摘要：

  Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium(II) iodide as the reductive coupling agent. Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the presence of a catalytic quantity of iron(III) complexes. Thus a comprehensive series of halo substituted esters were cyclized in excellent yield to the corresponding 4-, 5-, and 6-membered carbocycles. The reaction is extremely mild and selective as demonstrated by experiments wherein alkyl chlorides, acetals, and olefins remain completely intact under the reaction conditions. In addition to introducing a convenient procedure for preparing stereodefined spirocyclic systems, a new ring expansion sequence has been developed that appears extremely general for the preparation of various ring systems.

  DOI：

  10.1021/jo00077a053
• 作为产物：
  描述：

  Ethyl 2-(3-chloropropyl)-4-pentenoate 在 tris(dibenzoylmethano)iron(III) 、 对甲苯磺酸 盐酸 、 samarium diiodide 、 sodium hydride 、 二异丁基氢化铝 、 臭氧 、 三乙胺 、 sodium iodide 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 33.5h， 生成 trans-2-(5-Chloro-3-pentenyl)cyclopentanone
  参考文献：
  名称：

  Intramolecular nucleophilic acyl substitution reactions of halo-substituted esters and lactones. New applications of organosamarium reagents

  摘要：

  Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium(II) iodide as the reductive coupling agent. Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the presence of a catalytic quantity of iron(III) complexes. Thus a comprehensive series of halo substituted esters were cyclized in excellent yield to the corresponding 4-, 5-, and 6-membered carbocycles. The reaction is extremely mild and selective as demonstrated by experiments wherein alkyl chlorides, acetals, and olefins remain completely intact under the reaction conditions. In addition to introducing a convenient procedure for preparing stereodefined spirocyclic systems, a new ring expansion sequence has been developed that appears extremely general for the preparation of various ring systems.

  DOI：

  10.1021/jo00077a053