Dichloroacetic acid, 3-phenylpropyl ester | 87228-47-5

• 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: Dichloroacetic acid, 3-phenylpropyl ester
• 英文别名: 3-phenylpropyl 2,2-dichloroacetate
• CAS: 87228-47-5
• 化学式: C₁₁H₁₂Cl₂O₂
• 分子量: 247.121
• InChiKey: MQJYPHGGFSABDL-UHFFFAOYSA-N

物化性质

• 沸点：
  331.4±32.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Dichloroacetic acid, 3-phenylpropyl ester 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以254 mg的产率得到3-苯丙醇
  参考文献：
  名称：

  Using N-Nitrosodichloroacetamides to Conveniently Convert Linear Primary Amines into Alcohols

  摘要：

  The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.

  DOI：

  10.1080/00397911.2015.1061672
• 作为产物：
  描述：

  以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 Dichloroacetic acid, 3-phenylpropyl ester
  参考文献：
  名称：

  Using N-Nitrosodichloroacetamides to Conveniently Convert Linear Primary Amines into Alcohols

  摘要：

  The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.

  DOI：

  10.1080/00397911.2015.1061672

文献信息

• A FACILE SYNTHESIS OF CARBOXYLIC ESTERS AND CARBOXAMIDES BY THE USE OF 1,1′-DIMETHYLSTANNOCENE AS A CONDENSING REAGENT
  作者：Teruaki Mukaiyama、Junji Ichikawa、Masatoshi Asami

  DOI：10.1246/cl.1983.683

  日期：1983.5.5

  Various carboxylic esters or carboxamides are prepared in good yields under nearly neutral conditions from equimolar amounts of free carboxylic acids and alcohols or amines, respectively, by the use of 1,1′-dimethylstannocene as a condensing reagent.

  多种羧酸酯或酰胺可在近中性条件下，通过使用1,1'-二甲基二锡烷作为缩合剂，从等摩尔量的游离羧酸与醇或胺分别反应，以良好产率制备得到。
• MUKAIYAMA, TERUAKI;ICHIKAWA, JUNJI;ASAMI, MASATOSHI, CHEM. LETT., 1983, N 5, 683-686
  作者：MUKAIYAMA, TERUAKI、ICHIKAWA, JUNJI、ASAMI, MASATOSHI

  DOI：——

  日期：——
• Using <i>N</i>-Nitrosodichloroacetamides to Conveniently Convert Linear Primary Amines into Alcohols
  作者：Nicholas S. MacArthur、Linshu Wang、Blaine G. McCarthy、Charles E. Jakobsche

  DOI：10.1080/00397911.2015.1061672

  日期：2015.9.2

  The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.