(S)-2-(4-fluorophenyl)butanoic acid | 1095321-33-7

• 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-fluorophenyl)butanoic acid
• 英文别名: (2S)-2-(4-fluorophenyl)butanoic acid
• CAS: 1095321-33-7
• 化学式: C₁₀H₁₁FO₂
• 分子量: 182.195
• InChiKey: KQKOJJNAHZCQRX-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-fluorophenyl)butanoic acid 在 sodium azide 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 0.75h， 生成 (2S)-2-(4-fluorophenyl)butanoyl azide
  参考文献：
  名称：

  Antidotes to anthrax lethal factor intoxication. Part 3: Evaluation of core structures and further modifications to the C2-side chain

  摘要：

  Four core structures capable of providing sub-nanomolar inhibitors of anthrax lethal factor (LF) were evaluated by comparing the potential for toxicity, physicochemical properties, in vitro ADME profiles, and relative efficacy in a rat lethal toxin (LT) model of LF intoxication. Poor efficacy in the rat LT model exhibited by the phenoxyacetic acid series (3) correlated with low rat microsome and plasma stability. Specific molecular interactions contributing to the high affinity of inhibitors with a secondary amine in the C2-side chain were revealed by X-ray crystallography. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.095
• 作为产物：
  描述：

  (S)-3-((S)-2-(4-fluorophenyl)butanoyl)-4-isopropyloxazolidin-2-one 在 过氧化氢,锂盐(1:1) 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 (S)-2-(4-fluorophenyl)butanoic acid
  参考文献：
  名称：

  Antidotes to anthrax lethal factor intoxication. Part 3: Evaluation of core structures and further modifications to the C2-side chain

  摘要：

  Four core structures capable of providing sub-nanomolar inhibitors of anthrax lethal factor (LF) were evaluated by comparing the potential for toxicity, physicochemical properties, in vitro ADME profiles, and relative efficacy in a rat lethal toxin (LT) model of LF intoxication. Poor efficacy in the rat LT model exhibited by the phenoxyacetic acid series (3) correlated with low rat microsome and plasma stability. Specific molecular interactions contributing to the high affinity of inhibitors with a secondary amine in the C2-side chain were revealed by X-ray crystallography. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.095

文献信息

• [EN] INDANE DERIVATIVES AS MGLUR7 MODULATORS<br/>[FR] DÉRIVÉS D'INDANE UTILISÉS COMME MODULATEURS DE MGLUR7
  申请人：TAKEDA PHARMACEUTICALS CO

  公开号：WO2017131221A1

  公开（公告）日：2017-08-03

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4a and R4b are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy. The compounds of formula (I) are mGluR7 modulators.

  本发明提供了式（I）的化合物及其药学上可接受的盐，其中R1、R2、R3、R4a和R4b如规范中定义，其制备方法，含有它们的药物组合物以及它们在治疗中的用途。式（I）的化合物是mGluR7调节剂。
• Iron-Catalyzed Enantioselective Cross-Coupling Reactions of α-Chloroesters with Aryl Grignard Reagents
  作者：Masayoshi Jin、Laksmikanta Adak、Masaharu Nakamura

  DOI：10.1021/jacs.5b02277

  日期：2015.6.10

  The first iron-catalyzed enantioselective cross-coupling reaction between an organometallic compound and an organic electrophile is reported. Synthetically versatile racemic α-chloro- and α-bromoalkanoates were coupled with aryl Grignard reagents in the presence of catalytic amounts of an iron salt and a chiral bisphosphine ligand, giving the products in high yields with acceptable and synthetically

  报道了第一个铁催化的有机金属化合物和有机亲电试剂之间的对映选择性交叉偶联反应。在催化量的铁盐和手性双膦配体存在下，合成通用的外消旋 α-氯代和 α-溴代链烷酸酯与芳基格利雅试剂偶联，得到高产率的产物，具有可接受和合成有用的对映选择性（高达 91 :9)。通过简单的脱保护/重结晶，产生的 α-芳基链烷酸酯很容易转化为相应的具有高光学富集（er 高达 >99:1）的 α-芳基链烷酸。自由基探针实验的结果与涉及形成烷基自由基中间体的机制一致，该中间体以分子间方式经历随后的对映聚合芳基化。
• Determination of the Absolute Configuration of β-Chiral Primary Alcohols Using the Competing Enantioselective Conversion Method
  作者：Alexander S. Burns、Alexander J. Wagner、Jennifer L. Fulton、Kyle Young、Armen Zakarian、Scott. D. Rychnovsky

  DOI：10.1021/acs.orglett.7b01189

  日期：2017.6.2

  A method for determining the absolute configuration of β-chiral primary alcohols has been developed. Enantioenriched alcohols were acylated in the presence of either enantiomer of the enantioselective acylation catalyst HBTM, and the faster reaction was determined by measuring product conversion using 1H NMR spectroscopic analysis. An empirical mnemonic was developed that correlates the absolute configuration

  已经开发出确定β-手性伯醇的绝对构型的方法。在对映选择性酰化催化剂HBTM的任何一种对映异构体的存在下，将富含对映体的醇酰化，并通过使用1 H NMR光谱分析测量产物转化率来确定更快的反应。开发了经验助记符，其将醇的绝对构型与更快反应的催化剂相关联。该方法成功的底物包括在立体异构中心带有“指导基团”的伯醇。指导基团包括芳烃，杂芳烃，烯酮和卤化物。
• 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。
• INDANE DERIVATIVES AS MGLUR7 MODULATORS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP3408256A1

  公开（公告）日：2018-12-05