[1]naphthyl-carbamic acid-[1-(4-chloro-phenyl)-ethyl ester] | 858462-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [1]naphthyl-carbamic acid-[1-(4-chloro-phenyl)-ethyl ester]
• 英文别名: [1]Naphthyl-carbamidsaeure-[1-(4-chlor-phenyl)-aethylester]；1-(Naphthyl-(1)-carbamoyloxy)-1-(4-chlor-phenyl)-aethan
• CAS: 858462-79-0
• 化学式: C₁₉H₁₆ClNO₂
• 分子量: 325.795
• InChiKey: YVBHQOOFAGHIBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [1]naphthyl-carbamic acid-[1-(4-chloro-phenyl)-ethyl ester] 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.5h， 以3.21 g的产率得到methyl naphthalen-1-yl carbamic acid 1-(4-chlorophenyl)ethyl ester
  参考文献：
  名称：

  N to C Aryl Migration in Lithiated Carbamates: α-Arylation of Benzylic Alcohols

  摘要：

  We report a new mode of reactivity displayed by lithiated O-benzyl carbamates carrying an N-aryl substituent: upon lithiation, the N-aryl group is transferred cleanly from N to C. An arylation of the carbamate results, providing a route to alpha,alpha-arylated secondary or tertiary alcohols. We also report density functional theory calculations supporting the proposal that arylation proceeds through a dearomatizing attack on the aromatic ring, a significantly lower energy pathway than the 1,2-acyl transfer observed with related N-alkyl carbamates.

  DOI：

  10.1021/ja808959e
• 作为产物：
  描述：

  1-(4-氯苯基)乙醇 、 1-Alapha-萘异氰酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 [1]naphthyl-carbamic acid-[1-(4-chloro-phenyl)-ethyl ester]
  参考文献：
  名称：

  N to C Aryl Migration in Lithiated Carbamates: α-Arylation of Benzylic Alcohols

  摘要：

  We report a new mode of reactivity displayed by lithiated O-benzyl carbamates carrying an N-aryl substituent: upon lithiation, the N-aryl group is transferred cleanly from N to C. An arylation of the carbamate results, providing a route to alpha,alpha-arylated secondary or tertiary alcohols. We also report density functional theory calculations supporting the proposal that arylation proceeds through a dearomatizing attack on the aromatic ring, a significantly lower energy pathway than the 1,2-acyl transfer observed with related N-alkyl carbamates.

  DOI：

  10.1021/ja808959e

文献信息

• 48. Insecticidal activity and chemical constitution. Part I. Chlorinated p-chloroethylbenzenes
  作者：D. Woodcock

  DOI：10.1039/jr9490000203

  日期：——