2-丙酰苯基二乙基氨基甲酸酯 | 211449-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-丙酰苯基二乙基氨基甲酸酯
• 英文名称: 2-propionylphenyldiethylcarbamate
• 英文别名: (2-propanoylphenyl) N,N-diethylcarbamate
• CAS: 211449-25-1
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: ARPRUDIZUBQMPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-丙酰苯基二乙基氨基甲酸酯 在 水 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以50%的产率得到水杨酸
  参考文献：
  名称：

  A Baker–Venkataraman retro-Claisen cascade delivers a novel alkyl migration process for the synthesis of amides

  摘要：

  A simple extension of the carbamoyl Baker-Venkataraman rearrangement has been developed. If residual water in the reaction is not strictly excluded a Baker-Venkataraman retro-Claisen cascade takes place, giving amide products, in which an alkyl group apparently migrates between two functionalities of the substrate. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.077
• 作为产物：
  描述：

  2'-羟基苯丙酮 、 N,N-二乙基氯甲酰胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以32%的产率得到2-丙酰苯基二乙基氨基甲酸酯
  参考文献：
  名称：

  A Baker–Venkataraman retro-Claisen cascade delivers a novel alkyl migration process for the synthesis of amides

  摘要：

  A simple extension of the carbamoyl Baker-Venkataraman rearrangement has been developed. If residual water in the reaction is not strictly excluded a Baker-Venkataraman retro-Claisen cascade takes place, giving amide products, in which an alkyl group apparently migrates between two functionalities of the substrate. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.077

文献信息

• Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins
  作者：Alexey V. Kalinin、Alcides J.M. da Silva、Claudio C. Lopes、Rosangela S.C. Lopes、Victor Snieckus

  DOI：10.1016/s0040-4039(98)00977-0

  日期：1998.7

  A new carbamoyl Baker-Venkataraman rearrangement (4) which allows a general synthesis of substituted 4-hydroxycoumarins 8 in 43-82% overall yields is described; the intermediate arylketones 6 are efficiently prepared (59-91% yields) via a Directed ortho Metalation - Negishi cross coupling protocol from arylcarbamates 5 and the overall sequence provides a regiospecific anionic Friedel-Crafts complement for the construction of ortho-acyl phenols and coumarins. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A Baker–Venkataraman retro-Claisen cascade delivers a novel alkyl migration process for the synthesis of amides
  作者：Dana Ameen、Timothy J. Snape

  DOI：10.1016/j.tetlet.2015.02.077

  日期：2015.4

  A simple extension of the carbamoyl Baker-Venkataraman rearrangement has been developed. If residual water in the reaction is not strictly excluded a Baker-Venkataraman retro-Claisen cascade takes place, giving amide products, in which an alkyl group apparently migrates between two functionalities of the substrate. (C) 2015 Elsevier Ltd. All rights reserved.