3-acetamido-3-phenylpropanamide | 110425-61-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-acetamido-3-phenylpropanamide
• 英文别名: 3-acetylamino-3-phenyl-propionic acid amide；3-Acetylamino-3-phenyl-propionsaeure-amid；(+/-)-3-Acetamino-3-phenyl-propionamid
• CAS: 110425-61-1
• 化学式: C₁₁H₁₄N₂O₂
• mdl: MFCD24388157
• 分子量: 206.244
• InChiKey: GGVSJDCMJGLIRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R/S)-3-(acetylamino)-3-phenylpropanoic acid 在 硫酸 、 氨 作用下， 生成 3-acetamido-3-phenylpropanamide
  参考文献：
  名称：

  Rodionow; Kiselewa, Zhurnal Obshchei Khimii, 1948, vol. 18, p. 1905,1908

  摘要：

  DOI：

文献信息

• Transamidation reactions of β-lactams: A synthesis of (±)-dihydroperiphylline
  作者：Leslie Crombie、Raymond C.F. Jones、David Haigh

  DOI：10.1016/s0040-4039(00)85157-6

  日期：1986.1

  Whereas ammonolysis of -(halogenoalkyl)azetidin-2-ones affords medium ring azalactams transamidation, large or strained rings are not isolated, acyclic β-amino-amides being produced; two successive transamidative ring expansions from 4-phenyla-zetidin-2-one give a synthesis of (±)-dihydroperiphylline.

  -（卤代烷基）氮杂环丁烷-2-酮的氨解提供中等环的氮杂内酰胺转酰胺基作用，而没有分离出大的或应变的环，产生了无环的β-氨基酰胺。由4-苯基α-zetidin-2-one连续两次转酰胺基扩环，合成了（±）-二氢茶碱。
• Begley, Michael J.; Crombie, Leslie; Haigh, David, Journal of the Chemical Society. Perkin transactions I, 1993, # 17, p. 2027 - 2046
  作者：Begley, Michael J.、Crombie, Leslie、Haigh, David、Jones, Raymond C. F.、Osborne, Steven、Webster, Richard A. B.

  DOI：——

  日期：——
• Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870
  作者：Varsha Chhiba、Moira L. Bode、Kgama Mathiba、Wendy Kwezi、Dean Brady

  DOI：10.1016/j.molcatb.2011.12.005

  日期：2012.4

  A range of beta-aminonitriles (3-amino-3-phenylpropanenitrile and derivatives) were synthesised by reaction of various benzonitriles with acetonitrile and subsequent reduction of the resulting acrylonitrile products. These compounds were hydrolysed to the corresponding amides using the nitrile biocatalytic activity of Rhodococccus rhodochrous ATCC BAA-870. Results showed that the nitrile hydratase enzyme was enantioselective for these compounds, in particular 3-amino-3-p-tolylpropanenitrile and 3-amino-3-(4-methoxyphenyl)propanenitrile and the corresponding amides (up to 85% in one case). The reactions were performed at pH 9.0 after initial attempts at pH 7.0 were unsuccessful, most likely as a result of protonation of the 3-amino group at the lower pH. (C) 2012 Elsevier B.V. All rights reserved.
• Rodionow; Sworykina, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1948, p. 330,334, 338
  作者：Rodionow、Sworykina

  DOI：——

  日期：——
• CROMBIE L.; JONES R. C. F.; HAIGH D., TETRAHEDRON LETT., 27,(1986) N 42, 5151-5154
  作者：CROMBIE L.、 JONES R. C. F.、 HAIGH D.

  DOI：——

  日期：——