4-(4-chlorophenyl)-3-hydroxybutanoic acid | 6732-20-3

• 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: 4-(4-chlorophenyl)-3-hydroxybutanoic acid
• 英文别名: 4-(p-Chlor-phenyl)-3-hydroxy-buttersaeure；4-(p-Chlorphenyl)-3-hydroxybuttersaeure
• CAS: 6732-20-3
• 化学式: C₁₀H₁₁ClO₃
• 分子量: 214.649
• InChiKey: YDZMHVBZTPXGEP-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  374.9±32.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-3-hydroxybutanoic acid 、 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以27%的产率得到(3R,4S)-methyl 4-(4-chloro-3-(2-(4-fluorophenyl)acetamido)phenyl)-1-(4-(4-chlorophenyl)-3-hydroxybutanoyl)pyrrolidine-3-carboxylate
  参考文献：
  名称：

  Structure-Based Design of Potent and Selective Leishmania N-Myristoyltransferase Inhibitors

  摘要：

  Inhibitors of Leishmania N-myristoyltransferase (NMT), a potential target for the treatment of leishmaniasis, obtained from a high-throughput screen, were resynthesized to validate activity. Crystal structures bound to Leishmania major NMT were obtained, and the active diastereoisomer of one of the inhibitors was identified. On the basis of structural insights, enzyme inhibition was increased 40-fold through hybridization of two distinct binding modes, resulting in novel, highly potent Leishmania donovani NMT inhibitors with good selectivity over the human enzyme.

  DOI：

  10.1021/jm5011397
• 作为产物：
  描述：

  4-(p-Chlor-phenyl)-3-hydroxy-buttersaeurenitril 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-(4-chlorophenyl)-3-hydroxybutanoic acid
  参考文献：
  名称：

  4-（对-联苯甲酰基）-3-羟基丁酸及相关化合物的合成及抗炎活性。

  摘要：

  DOI：

  10.1021/jm00312a008

文献信息

• Process for producing optically active 3-halogenocarboxylic acid ester and 3-azidocarboxylic acid ester
  申请人：——

  公开号：US20030225301A1

  公开（公告）日：2003-12-04

  A process for producing an optically active 3-azide-carboxylic acid ester by reacting an optically active 3-hydroxycarboxylic acid ester and a thionyl halide in the presence of a basic substance in an organic solvent to produce an optically active 3-halogenocarboxylic acid ester which is then reacted with an azide salt represented by the formula: MN 3 (wherein M is an alkaline metal) in water or a mixture of water and a water soluble organic solvent.

  通过在有机溶剂中，在碱性物质存在下，将光学活性的3-羟基羧酸酯和硫酰卤在一起反应，产生光学活性的3-卤代羧酸酯，然后将其与由公式表示的偶氮盐（其中M是碱性金属）在水或水和水溶性有机溶剂的混合物中反应，从而生产光学活性的3-偶氮基羧酸酯的方法。
• Enantioseparation of 3-Hydroxycarboxylic Acids via Diastereomeric Salt Formation by 2-Amino-1,2-diphenylethanol (ADPE) and Cinchonidine
  作者：Srinivas Chandrasekaran、Masaki Tambo、Yuta Yamazaki、Tatsuro Muramatsu、Yusuke Kanda、Takuji Hirose、Koichi Kodama

  DOI：10.3390/molecules28010114

  日期：——

  Enantioseparation of 3-hydroxycarboxylic acids via diastereomeric salt formation was demonstrated using 2-amino-1,2-diphenylethanol (ADPE) and cinchonidine as the resolving agents. Racemic 3-hydroxy-4-phenylbutanoic acid (rac-1), 3-hydroxy-4-(4-chlorophenyl)butanoic acid (rac-2), and 3-hydroxy-5-phenylpentanoic acid (rac-3) were efficiently resolved using these resolving agents. Moreover, the successive

  使用 2-氨基-1,2-二苯基乙醇 (ADPE) 和辛可尼定作为拆分剂证明了 3-羟基羧酸通过非对映体盐形成的对映分离。外消旋 3-羟基-4-苯基丁酸 (rac-1)、3-羟基-4-(4-氯苯基)丁酸 (rac-2) 和 3-羟基-5-苯基戊酸 (rac-3)使用这些解析代理解析。此外，使用乙醇对 1 和辛可尼定的难溶性非对映体盐进行连续结晶，以高产率得到纯 (R)-1·辛可尼定盐。阐明了难溶性非对映体盐的晶体结构，并揭示了氢键和 CH/π 相互作用在增强难溶性非对映体盐的结构中起着重要作用。
• Process for producing optically active 3-halogenocarboxylic acid esters and 3-azide-carboxylic acid esters
  申请人：Takasago International Corporation

  公开号：EP1344763A1

  公开（公告）日：2003-09-17

  A process for producing an optically active 3-azide-carboxylic acid ester by reacting an optically active 3-hydroxycarboxylic acid ester and a thionyl halide in the presence of a basic substance in an organic solvent to produce an optically active 3-halogenocarboxylic acid ester which is then reacted with an azide salt represented by the formula: MN3 (wherein M is an alkaline metal) in water or a mixture of water and a water soluble organic solvent.

  一种生产光学活性 3-叠氮羧酸酯的工艺，在有机溶剂中，在碱性物质存在下，使光学活性 3-羟基羧酸酯和硫酰基卤反应，生成光学活性 3-卤代羧酸酯，然后使其与式 MN3（其中 M 为碱金属）代表的叠氮盐反应：MN3（其中 M 为碱金属）在水或水与水溶性有机溶剂的混合物中反应。
• US6903233B2
  申请人：——

  公开号：US6903233B2

  公开（公告）日：2005-06-07
• Structure-Based Design of Potent and Selective <i>Leishmania</i> <i>N</i>-Myristoyltransferase Inhibitors
  作者：Jennie A. Hutton、Victor Goncalves、James A. Brannigan、Daniel Paape、Megan H. Wright、Thomas M. Waugh、Shirley M. Roberts、Andrew S. Bell、Anthony J. Wilkinson、Deborah F. Smith、Robin J. Leatherbarrow、Edward W. Tate

  DOI：10.1021/jm5011397

  日期：2014.10.23

  Inhibitors of Leishmania N-myristoyltransferase (NMT), a potential target for the treatment of leishmaniasis, obtained from a high-throughput screen, were resynthesized to validate activity. Crystal structures bound to Leishmania major NMT were obtained, and the active diastereoisomer of one of the inhibitors was identified. On the basis of structural insights, enzyme inhibition was increased 40-fold through hybridization of two distinct binding modes, resulting in novel, highly potent Leishmania donovani NMT inhibitors with good selectivity over the human enzyme.