methyl naphthalen-2-yl carbamic acid 1-phenylethyl ester | 1118917-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl naphthalen-2-yl carbamic acid 1-phenylethyl ester
• CAS: 1118917-22-8
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: ZOFHAOWMQVFBMA-UHFFFAOYSA-N

物化性质

• 沸点：
  451.0±24.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 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：
  0.15
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl naphthalen-2-yl carbamic acid 1-phenylethyl ester 在 仲丁基锂 作用下， 以 四氢呋喃 、 1,3,4-trimethylimidazolidin-2-one 、 环己烷 为溶剂， 以57%的产率得到methylcarbamic acid 1-naphthalen-2-yl-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：

  1-phenylethyl naphthalen-2-ylcarbamate 、 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403 mg的产率得到methyl naphthalen-2-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