Ethyl 2,2-bis(3-iodopropyl)-2-phenylpentanoate | 152668-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 2,2-bis(3-iodopropyl)-2-phenylpentanoate
• 英文别名: ethyl 5-iodo-2-(3-iodopropyl)-2-phenylpentanoate
• CAS: 152668-20-7
• 化学式: C₁₆H₂₂I₂O₂
• 分子量: 500.158
• InChiKey: FHCQNFJSHHXRRI-UHFFFAOYSA-N

物化性质

• 沸点：
  422.8±45.0 °C(predicted)
• 密度：
  1.688±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Ethyl 2,2-bis(3-iodopropyl)-2-phenylpentanoate 在 三哌啶氧膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以84%的产率得到cis-5-Phenylbicyclo<3.3.0>octan-1-ol
  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)-2-phenyl-4-pentenoate 在 dimethyl sulfide borane 、 sodium acetate 、 一氯化碘 、 sodium iodide 、 环己烯 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 Ethyl 2,2-bis(3-iodopropyl)-2-phenylpentanoate
  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