N-Cl-(L)-Leucine

• 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-(L)-Leucine
• 英文别名: Chloroleucine；(2S)-2-(chloroamino)-4-methylpentanoic acid
• 化学式: C₆H₁₂ClNO₂
• 分子量: 165.62
• InChiKey: ASVRUJBTDNHQMI-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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-(L)-Leucine 在 hydroxide 作用下， 以 水 为溶剂， 生成 4-甲基-2-氧代戊酸
  参考文献：
  名称：

  Concerted base-promoted elimination in the decomposition ofN-halo amino acids

  摘要：

  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.

  DOI：

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

文献信息

• [EN] METHODS AND COMPOSITIONS FOR THE TREATMENT OF PAIN<br/>[FR] MÉTHODES ET COMPOSITIONS POUR LE TRAITEMENT DE LA DOULEUR
  申请人：HELLER ADAM

  公开号：WO2010017405A1

  公开（公告）日：2010-02-11

  The invention features methods, kits, and compositions for the treatment of pain.

  本发明涉及用于治疗疼痛的方法、试剂盒和组合物。
• Nitrenium ions in N-chloro-?-amino acids decomposition?
  作者：X. L. Armesto、M. Canle L.、M. Losada、J. A. Santaballa

  DOI：10.1002/kin.550250102

  日期：1993.1

  AbstractThis article deals with the kinetics of decomposition of four isomers: NCl‐(L)‐2‐Aminohexanoic acid, NCl‐(L)‐Leucine, NCl‐(L)‐Isoleucine, and NCl‐(L)‐tert‐Leucine, in mild acid and basic aqueous solution. An alternative mechanism for this process which takes place through a nitrenium‐like ion transition state is proposed. This mechanism is in consonance with the experimental data and with those available from the literature. © 1993 John Wiley & Sons, Inc.
• METHODS AND COMPOSITIONS FOR THE TREATMENT OF PAIN
  申请人：Heller, Adam

  公开号：EP2120555A1

  公开（公告）日：2009-11-25
• Methods and compositions for the treatment of pain
  申请人：Heller Adam

  公开号：US20080287866A1

  公开（公告）日：2008-11-20

  The invention features methods, kits, and compositions for the treatment of pain.
• US3943628A
  申请人：——

  公开号：US3943628A

  公开（公告）日：1976-03-16