S-2-氯戊酸 | 32644-12-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: S-2-氯戊酸
• 英文名称: (S)-2-chloropentanoic acid
• 英文别名: S-2-chlorovaleric acid；(2S)-2-chloropentanoic acid
• CAS: 32644-12-5
• 化学式: C₅H₉ClO₂
• 分子量: 136.578
• InChiKey: WZZRDRYYUVHLRD-BYPYZUCNSA-N

物化性质

• 沸点：
  219.3±13.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  8
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  S-2-氯戊酸 在 正丁基锂 、 sodium azide 、 dimethyl sulfide borane 、 palladium 10% on activated carbon 、 palladium on activated charcoal 、 氢气 、 三乙酰氧基硼氢化钠 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -70.0~135.0 ℃ 、344.75 kPa 条件下， 反应 84.58h， 生成 (R,S′)-5-(1-hydroxy-2-((1-(4-methoxyphenyl)pentan-2-yl)amino)ethyl)benzene-1,3-diol
  参考文献：
  名称：

  Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β2-adrenergic receptor

  摘要：

  The beta(2)-adrenergic receptor (beta(2)-AR) agonist [H-3]-(R,R')-methoxyfenoterol was employed as the marker ligand in displacement studies measuring the binding affinities (K-i values) of the stereoisomers of a series of 4'-methoxyfenoterol analogs in which the length of the alkyl substituent at alpha' position was varied from 0 to 3 carbon atoms. The binding affinities of the compounds were additionally determined using the inverse agonist [H-3]-CGP-12177 as the marker ligand and the ability of the compounds to stimulate cAMP accumulation, measured as EC50 values, were determined in HEK293 cells expressing the beta(2)-AR. The data indicate that the highest binding affinities and functional activities were produced by methyl and ethyl substituents at the alpha' position. The results also indicate that the K-i values obtained using [H-3]-(R,R')methoxyfenoterol as the marker ligand modeled the EC50 values obtained from cAMP stimulation better than the data obtained using [H-3]-CGP-12177 as the marker ligand. The data from this study was combined with data from previous studies and processed using the Comparative Molecular Field Analysis approach to produce a CoMFA model reflecting the binding to the beta(2)-AR conformation probed by [H-3]-(R,R')-4'-methoxyfenoterol. The CoMFA model of the agonist-stabilized beta(2)-AR suggests that the binding of the fenoterol analogs to an agonist-stabilized conformation of the beta(2)-AR is governed to a greater extend by steric effects than binding to the [H-3]-CGP-12177-stabilized conformation(s) in which electrostatic interactions play a more predominate role. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.030
• 作为产物：
  描述：

  L-正缬氨酸 在 盐酸 、 sodium nitrite 作用下， 反应 15.0h， 生成 S-2-氯戊酸
  参考文献：
  名称：

  琥珀木香：具有不同结构的酒精具有常见的嗅觉特征和对映异构体的明显差异

  摘要：

  只有一个的四个可能的反式的重要香料醇的异构体Norlimbanol ®（1）具有非常强的琥珀木质气味，异构体1A用（1' - [R，3小号，6'小号）绝对构型。它的对映异构体1B几乎无味，没有琥珀色木质特征，而非对映异构体1C和1D则较弱，只有最敏感的人才能察觉。同样是真实的全系列的感性类似物1，包括β-烷氧基醇。这些醚属于两个结构类别：[（2,2,6-三甲基环己基）氧基]-（参见3、4和16）或{[2-（叔丁基）环己基]氧基}烷-2-醇衍生物（见19和20 ;表）。允许各个羟基化侧链良好重叠的叠加模型为这两种类型的共有感知特性提供了初步的解释（图5）。亲脂性环己烷部分在该模型中仅表现出最小的重叠，表明相当大的分子可能具有相同的气味。（S）-配置β可通过对映酮的对映选择性还原，方便地大规模获得-烷氧基醇（方案9）。

  DOI：

  10.1002/hlca.200490237

文献信息

• Asymmetric Synthesis of 2-chloro- and 2-bromo-alkanoic acids by halogenation of α-D-glucofuranose-derived silyl ketene acetals
  作者：P Angibaud、J.L Chaumette、J.R Desmurs、L Duhamel、G Plé、J.Y Valnot、P Duhamel

  DOI：10.1016/0957-4166(95)00251-j

  日期：1995.8

  2-chloro-alkanoic acids 6 and 7 have been obtained the diastereoselective halogenation of chiral silyl ketene acetals 3a-f, and subsequent saponification of the resulting crude esters. Examples characterized by e.e. values up to 95% are reported. The diastereoface selectivity is independent of the silyl ketene acetal configuration.

  光学活性的（S）-2-溴-和2-氯-链烷酸6和7已经获得了手性甲硅烷基烯酮缩醛3a-f的非对映选择性卤化，随后将所得的粗酯皂化。报告了以ee值高达95％为特征的示例。非对映体的选择性与甲硅烷基烯酮缩醛构型无关。
• Enzymatic Hydrolysis and Selective Racemisation Reactions of α-Chloro Esters
  作者：Louise Haughton、Jonathan M. J. Williams

  DOI：10.1055/s-2001-13395

  日期：——

  The kinetic resolution of a-chloro esters was effected with good selectivity using CLEC (Cross-Linked Enzyme Crystals) enzymes. The selective racemisation of a-chloro esters in the presence of alpha -chloro acids enabled a successful dynamic kinetic resolution reaction to be performed.

  使用 CLEC（交联酶晶体）酶以良好的选择性实现α-氯酯的动力学拆分。在存在 α-氯酸的情况下，α-氯酯的选择性外消旋作用能够进行成功的动态动力学拆分反应。
• Asymmetric Transformation of 2-Phenyl- and 2-Chloroalkanoic Acids<i>via</i>Chiral Oxazolines
  作者：Saizo Shibata、Hajime Matsushita、Hajime Kaneko、Masao Noguchi、Masahiko Saburi、Sadao Yoshikawa

  DOI：10.1246/bcsj.55.3546

  日期：1982.11

  Asymmetric transformation of racemic 2-phenyl- and 2-chloroalkanoic acids via oxazolines into the corresponding optically active acids was investigated using (S)-phenylalaninol as a chiral auxiliary. The asymmetric transformation was performed by metalation of the oxazolines with butyllithium followed by protonation of the resulting lithiooxazolines. 2-Phenyl- and 2-chloroalkanoic acids were obtained in the optical yields of 29–53% and 45–73%, respectively, by the acidic hydrolysis of the chiral oxazolines thus formed. The mechanism of the asymmetric transformation was discussed.

  以（S）-苯丙氨醇为手性助剂，研究了外消旋2-苯基-和2-氯烷酸通过恶唑啉转化为相应光学活性酸的不对称转化。通过用丁基锂对恶唑啉进行金属化，然后对生成的锂氧唑啉进行质子化，实现了不对称转化。通过手性恶唑啉的酸性水解，分别获得了光学收率29-53%和45-73%的2-苯基-和2-氯烷酸。讨论了不对称转化的机理。
• Heppke, G.; Loetzsch, D.; Sharma, N. K., Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 241, p. 275 - 288
  作者：Heppke, G.、Loetzsch, D.、Sharma, N. K.、Demus, D.、Diele, S.、et al.

  DOI：——

  日期：——
• EP1981831A2
  申请人：——

  公开号：EP1981831A2

  公开（公告）日：2008-10-22