ethyl N-(2-(1-benzyloxycarbonylamino-1-methylethyl)phenyl)carbamate | 229326-22-1

• 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 N-(2-(1-benzyloxycarbonylamino-1-methylethyl)phenyl)carbamate
• 英文别名: benzyl N-[2-[2-(ethoxycarbonylamino)phenyl]propan-2-yl]carbamate
• CAS: 229326-22-1
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: KMPLTJRJYYAQKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl N-(2-(1-benzyloxycarbonylamino-1-methylethyl)phenyl)carbamate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以100%的产率得到ethyl N-(2-(1-amino-1-methylethyl)phenyl)carbamate
  参考文献：
  名称：

  Study of biscarbamates derived from 2-aminobenzylamines as models for alcohol prodrugs

  摘要：

  Unsubstituted N-arylcarbamate of title compound does not cyclize to the corresponding cyclic urea: with ROH liberation, under mild conditions (40 degrees C). Substitution of the benzylic position by two methyl groups promotes slow cyclisation while N-methylation of the N-aryl carbamate has a more important effect. Relative cyclisation rates are in agreement with barrier heights obtained from ab initio calculations. The calculations also suggest that the highest cyclisation rate of the latter is a consequence of the steric hindrance caused by the N-methyl substituent. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00139-8
• 作为产物：
  描述：

  2-(1-amino-1-methylethyl)aniline hydrochloride 在 三乙胺 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 ethyl N-(2-(1-benzyloxycarbonylamino-1-methylethyl)phenyl)carbamate
  参考文献：
  名称：

  Study of biscarbamates derived from 2-aminobenzylamines as models for alcohol prodrugs

  摘要：

  Unsubstituted N-arylcarbamate of title compound does not cyclize to the corresponding cyclic urea: with ROH liberation, under mild conditions (40 degrees C). Substitution of the benzylic position by two methyl groups promotes slow cyclisation while N-methylation of the N-aryl carbamate has a more important effect. Relative cyclisation rates are in agreement with barrier heights obtained from ab initio calculations. The calculations also suggest that the highest cyclisation rate of the latter is a consequence of the steric hindrance caused by the N-methyl substituent. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00139-8