(S)-2-(4-chlorophenyl)butanoic acid | 1095322-62-5

• 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)butanoic acid
• 英文别名: (2S)-2-(4-chlorophenyl)butanoic acid
• CAS: 1095322-62-5
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: CVZHTBMFVPENFE-VIFPVBQESA-N

物化性质

• 沸点：
  311.3±17.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-氨基噻唑 、 (S)-2-(4-chlorophenyl)butanoic acid 在 2,4,6-三甲基吡啶 、 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (S)-2-(4-chlorophenyl)-N-(thiazol-2-yl)butanamide
  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
• 作为产物：
  描述：

  4-chloro-α-ethyl-benzeneacetaldehyde 在 Jones reagent 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以92%的产率得到(S)-2-(4-chlorophenyl)butanoic acid
  参考文献：
  名称：

  无环烯烃的分子间对映选择性Heck-Matsuda芳基化：在β-芳基-γ-内酯和β-芳基醛的合成中的应用

  摘要：

  我们在本文中描述了一种用于无环烯丙基醇的对映选择性分子内Heck-Matsuda芳基化的合成方法。在Pd（TFA）2和手性的市售双恶唑啉配体的存在下，将芳基重氮四氟硼酸盐用作芳基化剂。该方法简单，稳健，可扩展至几克，并且适用范围广，可以合成一系列良好至高对映选择性和高产率的β-芳基-羰基化合物。这种新的对映选择性的Heck-Matsuda芳基化反应可以合成β-芳基-γ-内酯和β-芳基醛，它们在合成生物活性化合物（如（R）-baclofen，（R）-咯利普兰，（S）-姜黄烯，（S）-脱氢姜黄烯和（S）-肿瘤素。

  DOI：

  10.1021/jo400378g

文献信息

• Highly Enantioselective Direct Alkylation of Arylacetic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Craig E. Stivala、Armen Zakarian

  DOI：10.1021/ja205107x

  日期：2011.8.10

  A direct, highly enantioselective alkylation of arylacetic acids via enediolates using a readily available chiral lithium amide as a stereodirecting reagent has been developed. This approach circumvents the traditional attachment and removal of chiral auxiliaries used currently for this type of transformation. The protocol is operationally simple, and the chiral reagent is readily recoverable.

  已经开发出使用容易获得的手性氨基锂作为立体定向试剂通过烯二醇对芳基乙酸进行直接、高度对映选择性的烷基化。这种方法绕过了目前用于此类转化的手性助剂的传统附着和去除。该方案操作简单，手性试剂易于回收。
• US6365398B1
  申请人：——

  公开号：US6365398B1

  公开（公告）日：2002-04-02
• The first synthetic agonists of FFA2: Discovery and SAR of phenylacetamides as allosteric modulators
  作者：Yingcai Wang、Xianyun Jiao、Frank Kayser、Jiwen Liu、Zhongyu Wang、Malgorzata Wanska、Joanne Greenberg、Jennifer Weiszmann、Hongfei Ge、Hui Tian、Simon Wong、Ralf Schwandner、Taeweon Lee、Yang Li

  DOI：10.1016/j.bmcl.2009.11.112

  日期：2010.1

  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.
• Intermolecular Enantioselective Heck–Matsuda Arylations of Acyclic Olefins: Application to the Synthesis of β-Aryl-γ-lactones and β-Aryl Aldehydes
  作者：Caio C. Oliveira、Ricardo A. Angnes、Carlos Roque D. Correia

  DOI：10.1021/jo400378g

  日期：2013.5.3

  intermolecular Heck–Matsuda arylation of acyclic allylic alcohols. Aryldiazonium tetrafluoroborates were applied as arylating agents in the presence of Pd(TFA)2 and a chiral, commercially available, bisoxazoline ligand. The methodology is straightforward, robust, scalable up to a few grams, and of broad scope allowing the synthesis of a range of β-aryl-carbonyl compounds in good to high enantioselectivities

  我们在本文中描述了一种用于无环烯丙基醇的对映选择性分子内Heck-Matsuda芳基化的合成方法。在Pd（TFA）2和手性的市售双恶唑啉配体的存在下，将芳基重氮四氟硼酸盐用作芳基化剂。该方法简单，稳健，可扩展至几克，并且适用范围广，可以合成一系列良好至高对映选择性和高产率的β-芳基-羰基化合物。这种新的对映选择性的Heck-Matsuda芳基化反应可以合成β-芳基-γ-内酯和β-芳基醛，它们在合成生物活性化合物（如（R）-baclofen，（R）-咯利普兰，（S）-姜黄烯，（S）-脱氢姜黄烯和（S）-肿瘤素。