(S)-2-(4-chlorophenyl)-4-pentenoic acid | 494802-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-(4-chlorophenyl)-4-pentenoic acid
• 英文别名: (2S)-2-(4-chlorophenyl)pent-4-enoic acid
• CAS: 494802-93-6
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: LLSZDJYYZJMKEO-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-chlorophenyl)-4-pentenoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (S)-2-(4-Chloro-phenyl)-pent-4-enoic acid methylamide
  参考文献：
  名称：

  Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 2: structure–activity relationships for substituted 2-aryl-1-[ N -(methyl)- N -(phenylsulfonyl)amino]-4-(piperidin-1-yl)butanes

  摘要：

  (2S)-2-(3,4-二氯苯基)-1-[N-(甲基)-N-(苯基亚砜)氨基]-4-[螺(2,3-二氢苯并噻吩-3,4'-哌啶-1'-基)]丁烷 S-氧化物 (3) 已被鉴定为一种具有强效 CCR5 拮抗活性的先导结构化合物，其 IC50 值为 35 nM。本文中，我们描述了针对 C-2 苯基片段的需求和优化的结构-活性关系研究。研究发现，苯基对于 CCR5 拮抗活性至关重要，取代基仅限于在 3 位引入小型基团（如 13 和 16，当 X=H、3-F、3-Cl、3-Me 时）。(C) 2001 Elsevier Science Ltd. 出版。

  DOI：

  10.1016/s0960-894x(00)00639-9
• 作为产物：
  描述：

  在 甲醇 、 mercury dichloride 、 水 、 lithium hydroxide 作用下， 以 水 、 乙醇 为溶剂， 反应 18.0h， 生成 (2R)-2-(4-chlorophenyl)pent-4-enoic acid 、 (S)-2-(4-chlorophenyl)-4-pentenoic acid
  参考文献：
  名称：

  The first synthetic agonists of FFA2: Discovery and SAR of phenylacetamides as allosteric modulators

  摘要：

  Free fatty acid receptor 2 (FFA2) is a G-protein coupled receptor for which only short-chain fatty acids (SCFAs) have been reported as endogenous ligands. We describe the discovery and optimization of phenylacetamides as allosteric agonists of FFA2. These novel ligands can suppress adipocyte lipolysis in vitro and reduce plasma FFA levels in vivo, suggesting that these allosteric modulators can serve as pharmacological tools for exploring the potential function of FFA2 in various disease conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.112

文献信息

• Method for Resolution of Baclofen Salts
  申请人：Universite de Rouen

  公开号：US20190345098A1

  公开（公告）日：2019-11-14

  The invention relates to the field of resolution of chiral compounds existing in the form of two optical antipodes (enantiomers), such as Baclofen. More particularly, the invention relates to the production of the pure enantiomer (R)(−) Baclofen, of chemical nomenclature (R)-4-amino-3-(4-chlorophenyl)-butanoic acid, and the hydrogen maleate salt thereof. More specifically, the invention relates to the resolution of hydrogen maleate salts of racemic Baclofen by preferential crystallisation and particularly by the AS3PC method (auto-seeded and programmed polythermal preferential crystallisation).

  本发明涉及手性化合物的分离领域，其以两种光学异构体（对映异构体）的形式存在，例如巴氯芬。更具体地，本发明涉及制备纯对映异构体（R）（−）巴氯芬，化学命名为（R）-4-氨基-3-（4-氯苯基）-丁酸及其氢马来酸盐。更具体地，本发明涉及通过优先结晶和特别是AS3PC方法（自动种子和程序化多温度优先结晶）来分离混合物巴氯芬的氢马来酸盐。
• Method for resolution of baclofen salts
  申请人：Universite de Rouen

  公开号：US11078152B2

  公开（公告）日：2021-08-03

  The invention relates to the field of resolution of chiral compounds existing in the form of two optical antipodes (enantiomers), such as Baclofen. More particularly, the invention relates to the production of the pure enantiomer (R)(−) Baclofen, of chemical nomenclature (R)-4-amino-3-(4-chlorophenyl)-butanoic acid, and the hydrogen maleate salt thereof. More specifically, the invention relates to the resolution of hydrogen maleate salts of racemic Baclofen by preferential crystallisation and particularly by the AS3PC method (auto-seeded and programmed polythermal preferential crystallisation).

  本发明涉及以两种光学对映体（对映体）形式存在的手性化合物（如巴氯芬）的解析领域。更具体地说，本发明涉及化学命名为(R)-4-氨基-3-(4-氯苯基)-丁酸的纯对映体(R)(-)巴氯芬及其马来酸氢盐的生产。更具体地说，本发明涉及外消旋巴氯芬马来酸氢盐的优先结晶法，特别是 AS3PC 法（自动播种和编程多热优先结晶法）。
• Synthesis of enantiomerically enriched (S)-(+)-2-aryl-4-pentenoic acids and (R)-(−)-2-aryl-4-pentenamides via microbial hydrolysis of nitriles, a chemoenzymatic approach to stereoisomers of α,γ-disubstituted γ-butyrolactones
  作者：Mei-Xiang Wang、Sheng-Min Zhao

  DOI：10.1016/s0957-4166(02)00470-6

  日期：2002.8

  In the presence of the nitrile hydratase amidase-containing Rhodococcus sp. AJ270 whole cell catalyst. 2-aryl-4-pentenenitriles 1 underwent enantioselective hydrolysis under mild conditions to afford (R)-(-)-2-aryl-4-pentenoic acid amides 2 and (S)-(+)-2-aryl-4-pentenoic acids 3 in almost quantitative yield. The amidase involved in the cells shows very high S-enantioselectivity whereas the nitrite hydratase exhibits low to moderate S-enatitioselectivity. The synthesis of stereoisomers of chi,gamma-disubstituted gamma-butyrolactones from iodolactonization of (S)-(+)-2-aryl-4-pentenoic acid was demonstrated. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Highly enantioselective biotransformations of 2-aryl-4-pentenenitriles, a novel chemoenzymatic approach to ( R )-(−)-baclofen
  作者：Mei-Xiang Wang、Sheng-Min Zhao

  DOI：10.1016/s0040-4039(02)01449-1

  日期：2002.9

  Catalyzed by Rhodococcus sp. AJ270 microbial cells under mild conditions, a range of racemic 2-aryl-4-pentenenitriles 1 underwent effective hydrolysis to afford excellent yields of enantiomerically pure (R)-(-)-2-aryl-4-pentenamides 2 and (S)-(+)-2-aryl-4-pentenoic acids 3 in most cases. The application of this biotransformation has been shown by a two-step synthesis of (R)-(-)-baclcfen. (C) 2002 Elsevier Science Ltd. All rights reserved.
• [EN] METHOD FOR THE RESOLUTION OF BACLOFEN SALTS<br/>[FR] PROCÉDÉ DE DÉDOUBLEMENT DE SELS DE BACLOFÈNE
  申请人：UNIV ROUEN

  公开号：WO2018015677A1

  公开（公告）日：2018-01-25

  La présente invention concerne le domaine du dédoublement de composés chiraux existant sous la forme de deux antipodes optiques (énantiomères), comme le Baclofène. Plus particulièrement, l'invention concerne la préparation de l'énantiomère pur (R)(-) Baclofène, de nomenclature chimique acide (R)-4-amino-3-(4-chlorophényl)-butanoïque et de son sel d'hydrogénomaléate. Tout spécialement, la présente invention concerne le dédoublement des sels d'hydrogénomaléate du Baclofène racémique par cristallisation préférentielle et notamment par le procédé AS3PC (cristallisation préférentielle polythermique programmée et auto-ensemencée).