2-azido-propionyl chloride | 55689-46-8

• 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: 2-azido-propionyl chloride
• 英文别名: α-azidopropionyl chloride；2-Azidopropanoyl chloride
• CAS: 55689-46-8
• 化学式: C₃H₄ClN₃O
• 分子量: 133.537
• InChiKey: FSWYXCKDYOIJDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-azido-propionyl chloride 、 D-氨基葡萄糖盐酸盐 在 sodium hydroxide 作用下， 生成 2-((Ξ)-2-azido-propionylamino)-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  Bertho; Meier, Justus Liebigs Annalen der Chemie, 1932, vol. 495, p. 113,115, 119

  摘要：

  DOI：
• 作为产物：
  描述：

  2-叠氮丙酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 2-azido-propionyl chloride
  参考文献：
  名称：

  三取代氮丙啶的催化不对称合成

  摘要：

  描述了一种由亚胺和重氮化合物直接不对称催化合成三取代氮丙啶的方法。虽然未活化的亚胺对重氮碳被二取代的 α-重氮羰基化合物没有反应性，但 N-Boc 亚胺与 α-重氮酯和 α-重氮-N-酰基恶唑烷酮反应生成具有优异非对映选择性和对映选择性的三取代氮丙啶。

  DOI：

  10.1021/ja203754p

文献信息

• Freudenberg; Eichel; Leutert, Chemische Berichte, 1932, vol. 65, p. 1183,1190
  作者：Freudenberg、Eichel、Leutert

  DOI：——

  日期：——
• Freudenberg; Keller, Chemische Berichte, 1938, vol. 71, p. 334
  作者：Freudenberg、Keller

  DOI：——

  日期：——
• Dynamic Enzymatic Resolution of Thioesters
  作者：Pil-Je Um、Dale G. Drueckhammer

  DOI：10.1021/ja980445b

  日期：1998.6.1

  A detailed investigation of several issues related to the enzymatic resolution of thioesters under conditions of continuous racemization of substrate was conducted. The kinetic acidity of the alpha-protons of a series of alpha-substituted propionate thioesters was studied. It was found that the rate of alpha-proton exchange could be enhanced as much as 20-fold by variation of the thiol moiety, increasing the range of compounds to which enzymatic dynamic resolution may be applied. The relative rates of hydrolysis of ethyl butyrate and ethyl thiobutyrate by several enzymes commonly used in enzymatic resolution were determined. All of the enzymes studied exhibited similar rates of thioester and oxoester hydrolysis except for the esterase from pig liver, which showed very low activity in thioester hydrolysis. Dynamic resolution of the propargyl and trifluoroethyl thioesters of alpha-phenylpropionate was conducted using subtilisin Carlsberg as a catalyst. These examples demonstrated that enzymatic dynamic resolution can be applied even when the rate of alpha-proton exchange and the enantioselectivity of the enzyme are fairly low. A dynamic enzymatic transesterification procedure was demonstrated in the resolution of the trifluoroethyl thioester of alpha-(2,4-dichlorophenoxy)propionate, and product was obtained in 93% ee. This work helps expand and define the scope of enzymatic dynamic resolution of thioesters.
• Mono-α-aminoacyl and Mono-α-dipeptide Triglycerides
  作者：W. Frederick Huber

  DOI：10.1021/ja01606a036

  日期：1955.1
• Wieland,T.; Hennig,H.J., Chemische Berichte, 1960, vol. 93, p. 1236 - 1246
  作者：Wieland,T.、Hennig,H.J.

  DOI：——

  日期：——