丙氨酸,N-氯-2-甲基- | 98022-90-3

• 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
• 中文名称: 丙氨酸,N-氯-2-甲基-
• 英文名称: N-chloro-alpha-aminoisobutyric acid
• 英文别名: 2-(Chloroamino)-2-methylpropanoic acid
• CAS: 98022-90-3
• 化学式: C₄H₈ClNO₂
• 分子量: 137.566
• InChiKey: JDWHRUJSFVABTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙氨酸,N-氯-2-甲基- 以 水 为溶剂， 以41%的产率得到丙酮
  参考文献：
  名称：

  Concerted Grob Fragmentation in N-Halo-.alpha.-amino Acid Decomposition

  摘要：

  The Grob fragmentation of N-halo-alpha-amino acids in aqueous solution has been studied, being first order in N-halo-alpha-amino acid and pH-independent. The substituents on the C-2 and N atoms strongly affect the reaction rate. Structure reactivity correlations for C-2 substituents provide rho* values of -3.9 and -4.1 for N-Cl and N-Br compounds, respectively. The same correlations for N substituents lead to rho* values of -2.1 and -1.9 for N-Cl and N-Br compounds. The transition state (TS) can be generally described as product-like, its structure and characteristics being significantly affected by the substituents on the C-2 and an the N atoms. In conclusion, the reaction is a DEDN concerted and slightly nonsynchronous two-stage process.

  DOI：

  10.1021/jo00095a048
• 作为产物：
  描述：

  2-甲基丙氨酸 在 氯 作用下， 生成 丙氨酸,N-氯-2-甲基-
  参考文献：
  名称：

  α-amino acids chlorination in aqueous media

  摘要：

  The reaction of chlorination of alpha-amino acids for 6 < pH < 11 has been studied. The reaction is an aliphatic electrophilic substitution, the rate determining step being the transfer of the chlorine atom between the HOCl oxygen and the nitrogen of the alpha-amino acid free amino group.

  DOI：

  10.1016/s0040-4020(01)80525-1

文献信息

• α-amino acids chlorination in aqueous media
  作者：X.L. Armesto、M.L. Canle、J.A. Santaballa

  DOI：10.1016/s0040-4020(01)80525-1

  日期：1993.1

  The reaction of chlorination of alpha-amino acids for 6 < pH < 11 has been studied. The reaction is an aliphatic electrophilic substitution, the rate determining step being the transfer of the chlorine atom between the HOCl oxygen and the nitrogen of the alpha-amino acid free amino group.
• Awad, Riad; Hussain, Anwar; Crooks, Peter A., Journal of the Chemical Society. Perkin transactions II, 1990, # 7, p. 1233 - 1238
  作者：Awad, Riad、Hussain, Anwar、Crooks, Peter A.

  DOI：——

  日期：——
• Concerted Grob Fragmentation in N-Halo-.alpha.-amino Acid Decomposition
  作者：X. L. Armesto、M. Canle L.、M. Losada、J. A. Santaballa

  DOI：10.1021/jo00095a048

  日期：1994.8

  The Grob fragmentation of N-halo-alpha-amino acids in aqueous solution has been studied, being first order in N-halo-alpha-amino acid and pH-independent. The substituents on the C-2 and N atoms strongly affect the reaction rate. Structure reactivity correlations for C-2 substituents provide rho* values of -3.9 and -4.1 for N-Cl and N-Br compounds, respectively. The same correlations for N substituents lead to rho* values of -2.1 and -1.9 for N-Cl and N-Br compounds. The transition state (TS) can be generally described as product-like, its structure and characteristics being significantly affected by the substituents on the C-2 and an the N atoms. In conclusion, the reaction is a DEDN concerted and slightly nonsynchronous two-stage process.
• Kinetic study of the chlorine transfer fromN-chlorosuccinimide to amino compounds
  作者：J. M. Antelo、F. Arce、J. Crugeir、M. Paraj�

  DOI：10.1002/(sici)1099-1395(199708)10:8<631::aid-poc924>3.0.co;2-w

  日期：1997.8

  A kinetic study of the reactions of N-chlorosuccinimide (NCS) with glycine (Gly), sarcosine (Sar), 2-methylalanine (2MA), proline (Pro) and pyrrolidine (Pyr) was carried out, The reactions were found to be first order with respect to both NCS and the amine or amino acid and order - 1 in proton concentration, In order to calculate the experimental activation parameters, the effect of temperature on the reaction rates was studied, The ionic strength and buffer concentration were found to have no effect on the rate constant, A reaction mechanism involving Cl+ transfer from NCS to the amine or amino acid to form an N-chloro compound is proposed. (C) 1997 by John Wiley & Sons, Ltd.