N-chloro-L-valine | 52316-70-8

• 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: N-chloro-L-valine
• 英文别名: N-chlorovaline；N-Cl-Valine；Chlorovaline；(2S)-2-(chloroamino)-3-methylbutanoic acid
• CAS: 52316-70-8
• 化学式: C₅H₁₀ClNO₂
• 分子量: 151.593
• InChiKey: YQYBDANXQKBAKJ-BYPYZUCNSA-N

物化性质

• 沸点：
  240.9±42.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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-chloro-L-valine 在 hydroxide 作用下， 以 水 为溶剂， 生成 2-氧代-3-甲基丁酸
  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
• 作为产物：
  描述：

  L-缬氨酸 在 次氯酸 作用下， 生成 N-chloro-L-valine
  参考文献：
  名称：

  General base catalysis in the decomposition ofN-Cl-Valine in aqueous solution

  摘要：

  AbstractThis article analyzes the kinetics of the decomposition of N‐Cl‐Valine in aqueous solution, which is formed rapidly by chlorination of Valine with sodium hypochlorite. A general‐base catalyzed process not yet described is reported. The experimental evidence shows two competitive decomposition paths: an unimolecular concerted fragmentation process (k = (1.8 ± 0.1) · 10−4 s−1 at 298 K) and the other one is an E2 elimination process whose importance increases with pH and depends on the nature and the concentration of the bases present in the medium. © 1994 John Wiley & Sons, Inc.

  DOI：

  10.1002/kin.550261008

文献信息

• 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：——
• US7265140B2
  申请人：——

  公开号：US7265140B2

  公开（公告）日：2007-09-04
• [EN] HCV NUCLEOSIDE INHIBITOR<br/>[FR] INHIBITEUR NUCLÉOSIDIQUE DU HCV
  申请人：MEDIVIR AB

  公开号：WO2008043704A1

  公开（公告）日：2008-04-17

  [EN] 4-Amino-1-((2R,3S,4S,5R)-5-azido-4hydroxy-5-hydroxymethyl-3-methyl-tetrahyclrofuran-2- yl)-1 H-pyrimidin-2-one(22) are hepatitis C (HCV) polymerase inhibitors. Also disclosed are compositions and methods for inhibiting HCV and treating HCV-mediated diseases, processes for making the compounds and synthetic intermediates employed in the process.
  [FR] La présente invention concerne des 4-amino-1-((2R,3S,4S,5R)-5-azido-4-hydroxy-5-hydroxyméthyl-3-méthyl-tétrahydrofuran-2-yl)-1-H-pyrimidin-2-one(22) qui sont des inhibiteurs de la polymérase du virus de l'hépatite C (HCV). L'invention concerne également des compositions et des procédés permettant d'inhiber le HCV et de traiter les maladies induites par le HCV, des procédés de fabrication des composés et les intermédiaires synthétiques utilisés dans les procédés.
• [EN] PRODRUGS TO THYROID HORMONE ANALOGS<br/>[FR] PROMÉDICAMENTS POUR ANALOGUES DE L'HORMONE THYROÏDIENNE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2009037172A1

  公开（公告）日：2009-03-26

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts and esters thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as obesity, hyperlipidemia, hypercholesterolemia and diabetes and other related disorders and diseases, and may be useful for other diseases such as NASH, atherosclerosis, cardiovascular diseases, hypothyroidism, thyroid cancer and other disorders and diseases related thereto.
• 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.