methyl 1-(4-chlorophenyl)-1-phenyl acetate

• 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: methyl 1-(4-chlorophenyl)-1-phenyl acetate
• 英文别名: methyl (2R)-2-(4-chlorophenyl)-2-phenylacetate
• 化学式: C₁₅H₁₃ClO₂
• 分子量: 260.72
• InChiKey: RFEJSDKMRLRIMA-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,4-环己二烯 、 methyl 2-(4-chlorophenyl)-2-diazoacetate 在 Rh₂((S)-N-(dodecylbenzenesulfonyl)prolinate)4 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 正己烷 、 苯 为溶剂， 反应 2.0h， 生成 methyl 1-(4-chlorophenyl)-1-phenyl acetate 、 methyl 1-(4-chlorophenyl)-1-phenyl acetate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Diarylacetates and 4,4-Diarylbutanoates. A Formal Asymmetric Synthesis of (+)-Sertraline

  摘要：

  The intermolecular C-H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N (dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4)) can be effectively carried out on cyclohexadienes, leading to the asymmetric synthesis of diarylacetates. The reaction of vinyldiazoacetates with cyclohexadienes results in an unprecedented carbenoid reaction that is formally a combined C-H insertion/Cope rearrangement. The synthetic utility of this novel transformation was demonstrated by its utilization in a formal asymmetric synthesis of (+)-sertraline.

  DOI：

  10.1021/ol9905699

文献信息

• Catalytic Asymmetric Synthesis of Diarylacetates and 4,4-Diarylbutanoates. A Formal Asymmetric Synthesis of (+)-Sertraline
  作者：Huw M. L. Davies、Douglas G. Stafford、Tore Hansen

  DOI：10.1021/ol9905699

  日期：1999.7.1

  The intermolecular C-H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N (dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4)) can be effectively carried out on cyclohexadienes, leading to the asymmetric synthesis of diarylacetates. The reaction of vinyldiazoacetates with cyclohexadienes results in an unprecedented carbenoid reaction that is formally a combined C-H insertion/Cope rearrangement. The synthetic utility of this novel transformation was demonstrated by its utilization in a formal asymmetric synthesis of (+)-sertraline.