(S)-cyclohex-1-enyl-hydroxy-phenylacetic acid | 268216-68-8

• 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)-cyclohex-1-enyl-hydroxy-phenylacetic acid
• 英文别名: (S)-Cyclohexenyl phenyl glycolic acid；(S)-Cyclohex-1-enyl-hydroxy-phenyl-acetic acid；(2S)-2-(cyclohexen-1-yl)-2-hydroxy-2-phenylacetic acid
• CAS: 268216-68-8
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: KFWYLIODEGTZGK-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (S)-cyclohex-1-enyl-hydroxy-phenylacetic acid 在 10percent Pd/C 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以94%的产率得到(S)-2-环己基-2-苯基乙醇酸
  参考文献：
  名称：

  Chiral Mandelic Acid Template Provides a Highly Practical Solution for (S)-Oxybutynin Synthesis

  摘要：

  DOI：

  10.1021/jo005562f
• 作为产物：
  描述：

  (2R,5S)-2-tert-butyl-5-(1-hydroxycyclohexyl)-5-phenyl-[1,3]dioxolan-4-one 在 氢氧化钾 、 氯化亚砜 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 (S)-cyclohex-1-enyl-hydroxy-phenylacetic acid
  参考文献：
  名称：

  Chiral Mandelic Acid Template Provides a Highly Practical Solution for (S)-Oxybutynin Synthesis

  摘要：

  DOI：

  10.1021/jo005562f

文献信息

• Organic Compounds
  申请人：Press Neil John

  公开号：US20090048281A1

  公开（公告）日：2009-02-19

  Compounds of Formula (I); in salt or zwitterionic form wherein R 1 , R 2 , R 3 and R 4 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by the muscarinic M3 receptor, especially inflammatory or obstructive airways diseases. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

  式（I）的化合物；以盐或双电离形式存在，其中R1，R2，R3和R4具有规范中指示的含义，可用于治疗由肌肉型M3受体介导的疾病，尤其是炎症性或阻塞性呼吸道疾病。还描述了含有该化合物的制药组合物和制备该化合物的过程。
• Stereoselective process for alkyl phenylglycolic acids
  申请人：Sepracor Inc.

  公开号：US06376684B1

  公开（公告）日：2002-04-23

  A process for preparing an alkyl phenylglycolic acid is disclosed. It follows the sequence of condensing a substituted acetaldehyde with mandelic acid to provide a 5-phenyl-1,3-dioxolan-4-one, which is condensed with an alkyl ketone or aldehyde to provide a 5-(1-hydroxyalkyl)-5-phenyl-1,3-dioxolan-4-one, which is dehydrated to a 5-(1-alkenyl)-5-phenyl-1,3-dioxolan-4-one. The 5-(1-alkenyl)-5-phenyl-1,3-dioxolan-4-one may be hydrolyzed and reduced to an &agr;-alkylphenylglycolic acid or the hydrolysis and reduction steps may be reversed. The process enables the production of single enantiomers of cyclohexylphenylglycolic acid (CHPGA). An analogous process for racemic CHPGA is disclosed employing racemic mandelic acid and acetone. Novel intermediates in the process are also disclosed.

  本发明揭示了一种制备烷基苯基乙醇酸的方法。该方法的步骤为：首先将取代乙醛与苯甲酸缩合，得到5-苯基-1,3-二氧杂环戊-4-酮，然后将其与烷基酮或醛缩合，得到5-(1-羟基烷基)-5-苯基-1,3-二氧杂环戊-4-酮，随后进行脱水反应，得到5-(1-烯基)-5-苯基-1,3-二氧杂环戊-4-酮。可以将5-(1-烯基)-5-苯基-1,3-二氧杂环戊-4-酮水解还原，得到α-烷基苯基乙醇酸，也可以将水解还原步骤反转。该方法能够生产环己基苯基乙醇酸（CHPGA）的单对映体。本发明还揭示了一种类似的方法，用于制备外消旋的CHPGA，该方法采用外消旋的苯甲酸和丙酮。同时还揭示了该方法中的新型中间体。
• Quinuclidine derivatives and their use as muscarinic M3 receptor antagonists
  申请人：Novartis AG

  公开号：US08084463B2

  公开（公告）日：2011-12-27

  Compounds of Formula (I); in salt or zwitterionic form wherein R1, R2, R3 and R4 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by the muscarinic M3 receptor, especially inflammatory or obstructive airways diseases. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

  公式（I）的化合物；以盐或双离子形式存在，其中R1、R2、R3和R4的含义如规范中所示，可用于治疗由肌肉型M3受体介导的疾病，尤其是炎症性或阻塞性呼吸道疾病。还描述了包含这些化合物的制药组合物和制备这些化合物的过程。
• QUINUCLIDINE DERIVATIVES AND THEIR USE AS MUSCARINIC M3 RECEPTOR ANTAGONISTS
  申请人：Press Neil John

  公开号：US20100168132A1

  公开（公告）日：2010-07-01

  Compounds of Formula (I) ; in salt or zwitterionic form wherein R 1 , R 2 , R 3 and R 4 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by the muscarinic M3 receptor, especially inflammatory or obstructive airways diseases. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

  式(I)的化合物；以盐或双电离形式存在，其中R1，R2，R3和R4的含义如规范中所示，对于治疗由肌肉型M3受体介导的情况，特别是炎症性或阻塞性气道疾病是有用的。还描述了包含这些化合物的制药组合物和制备这些化合物的过程。
• Quinuclidine derivatives and their use as muscarinic m3 receptor antagonists
  申请人：Novartis AG

  公开号：US07723356B2

  公开（公告）日：2010-05-25

  Compounds of Formula (I); in salt or zwitterionic form wherein R1, R2, R3 and R4 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by the muscarinic M3 receptor, especially inflammatory or obstructive airways diseases. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

  式(I)的化合物；以盐或双电离形式存在，其中R1、R2、R3和R4的含义如规范所示，可用于治疗由肌肉型M3受体介导的疾病，特别是炎症性或阻塞性呼吸道疾病。还描述了含有该化合物的制药组合物和制备该化合物的方法。