[1]naphthyl-carbamic acid-(1-phenyl-ethyl ester) | 119994-28-4

• 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-phenyl-ethyl ester)
• 英文别名: α-Naphthyl-carbamidsaeure-dl-α-phenaethylester；[1]Naphthyl-carbamidsaeure-(1-phenyl-aethylester)；1-phenylethyl N-naphthalen-1-ylcarbamate
• CAS: 119994-28-4
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: ZTZHHYAALZEMIS-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C
• 沸点：
  420.6±24.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [1]naphthyl-carbamic acid-(1-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3.19 g的产率得到methyl naphthalen-1-yl carbamic acid 1-phenylethyl 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：

  苏合香醇 、 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-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

• Potapov, V. M.; Panova, G. V.; Pekshueva, E. G., Journal of general chemistry of the USSR, 1981, vol. 51, # 6, p. 1027 - 1030
  作者：Potapov, V. M.、Panova, G. V.、Pekshueva, E. G.

  DOI：——

  日期：——
• N to C Aryl Migration in Lithiated Carbamates: α-Arylation of Benzylic Alcohols
  作者：Jonathan Clayden、William Farnaby、Damian M. Grainger、Ulrich Hennecke、Michele Mancinelli、Daniel J. Tetlow、Ian H. Hillier、Mark A. Vincent

  DOI：10.1021/ja808959e

  日期：2009.3.18

  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.