N-Cl-α-Alanine | 70303-54-7

• 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: N-Cl-α-Alanine
• 英文别名: N-chloro-L-alanine；N-chloroalanine；N-Cl-Ala；chloro-L-alanine；(2S)-2-(chloroamino)propanoic acid
• CAS: 70303-54-7
• 化学式: C₃H₆ClNO₂
• 分子量: 123.539
• InChiKey: TYZYNGFWGHGRBZ-REOHCLBHSA-N

物化性质

• 沸点：
  237.2±42.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  7
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Cl-α-Alanine 以 水 为溶剂， 以77%的产率得到乙醛
  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：

  L-丙氨酸 在 次氯酸 作用下， 生成 N-Cl-α-Alanine
  参考文献：
  名称：

  N Reactivity vs. O reactivity in aqueous chlorination

  摘要：

  AbstractNitrogenated compounds react with hypochlorous acid yielding N‐chloro compounds. In principle, α‐amino acids chlorination may take place on the oxygen of the carboxylic group or on the nitrogen of the amino group. In this framework, we discuss the different reactivities of nitrogen and oxygen towards chlorine, and come to the conclusion that the nitrogen is the preferred reaction site in α‐amino acids chlorination. © 1994 John Wiley & Sons, Inc.

  DOI：

  10.1002/kin.550261108

文献信息

• Manufacturing processes for Se-methyl-L-selenocysteine
  申请人：Sami Labs Limited

  公开号：US06794537B1

  公开（公告）日：2004-09-21

  Convenient processes are described for the synthesis of L-Se-methyselenocysteine from chloroalanine derivatives. The process is easily extendable to other selenium substituted amino acids. DL-Se-methyselenocysteine is easily obtained by a benzaldehyde-catalyzed racemization of L-Se-methyselenocysteine.

  方便的方法用于从氯丙氨酸衍生物合成L-Se-甲硒氨酸。该过程易于扩展到其他硒取代的氨基酸。通过苯甲醛催化的L-Se-甲硒氨酸的外消旋化反应，容易获得DL-Se-甲硒氨酸。
• Concerted base-promoted elimination in the decomposition ofN-halo amino acids
  作者：X. L. Armesto、M. Canle、M. V. Garc�a、M. Losada、J. A. Santaballa

  DOI：10.1002/(sici)1099-1395(199608)9:8<552::aid-poc820>3.0.co;2-r

  日期：1996.8

  N-Chloroamino acids are unstable in aqueous solution and decompose through different pathways depending on the reaction conditions, yielding precursors of carcinogenic and/or mutagenic compounds, One of these pathways is a 1,2-elimination process, which has scarcely received any attention and for which no systematic analysis is available, The process is first order relative to the N-chloroamino acid and to that of hydroxide ion, The use of 2,2,2-trifluoroethanol and 1,1,1,3,3,3-hexafluoropropan-2-ol buffer solutions established that the process is general-base catalysed, The reaction rate is affected by the presence of a methyl group on the nitrogen atom and the nature of the leaving group, The results show an important steric effect due to the alkyl substituents on the alpha-carbon. With bulky alkyl substituents on the a-carbon, and in particular in the case of N-alkylamino acids, the catalytic effect increases as the base strength decreases. To characterize the transition state, Bronsted's beta and beta(lg) were used. A More O'Ferrall-Jencks diagram shows the transition state structure changing from carbanion like to nitrenium-like, a large perpendicular effect being evident, The reaction proceeds through a concerted mechanism A(xh)D(H)D(N) instead of the stepwise A(xh)D(H) double dagger+D-N proposed earlier.
• 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：——
• Pressure and pH dependence of the kinetics of decarboxylative dechlorination of N-chloro-l-alanine
  作者：Michael C. Brown、Jason M. Lepree、Kenneth A. Connors

  DOI：10.1002/(sici)1097-4601(1996)28:11<791::aid-kin1>3.0.co;2-i

  日期：——

  The kinetics of decarboxylative dechlorination of N-chloroalanine were studied at 25 degrees in aqueous HCl solutions covering the pH range 1.4 to 2.8. These data were compared with literature results, and were interpreted in terms of first-order reactions of the cationic, uncharged, and anionic forms of the reactant. Pressure effect studies on the reaction of the anionic species yielded a volume of activation estimate of + 50 +/- 3 cm(3) mol(-1). This result is consistent with a concerted fragmentation process. (C) 1996 John Wiley & Sons.
• 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.