5-chloro-2-[3-(3-hydroxyphenyl)-3-oxopropyl]benzoic acid | 177747-93-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 5-chloro-2-[3-(3-hydroxyphenyl)-3-oxopropyl]benzoic acid
• CAS: 177747-93-2
• 化学式: C₁₆H₁₃ClO₄
• 分子量: 304.73
• InChiKey: VHNSPUZFAAOMME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-2-[3-(3-hydroxyphenyl)-3-oxopropyl]benzoic acid 在 dimethyl sulfide borane 、 硫酸 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 36.0h， 生成 (R)-5-chloro-2-[3-hydroxy-3-(3-hydroxyphenyl)propyl]benzoic acid methyl ester
  参考文献：
  名称：

  Practical Route to a New Class of LTD₄ Receptor Antagonists

  摘要：

  A general approach to the synthesis of a new class of LTD(4) antagonists is presented. The key diarylpropane framework was prepared by Claisen-Schmidt condensation and selective reduction of the enone. Depending on the bridge to the 7-chloroquinaldine moiety, alkylation or Heck coupling methodology was developed. The chiral sulfides were introduced by asymmetric reduction of the diarylpropanone intermediates and subsequent inversion of the chiral center.

  DOI：

  10.1021/jo952103j
• 作为产物：
  描述：

  6-chloro-3-hydroxyisobenzofuran-1(3H)-one 在 Wilkinson's catalyst 盐酸 、 sodium hydroxide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 生成 5-chloro-2-[3-(3-hydroxyphenyl)-3-oxopropyl]benzoic acid
  参考文献：
  名称：

  Practical Route to a New Class of LTD₄ Receptor Antagonists

  摘要：

  A general approach to the synthesis of a new class of LTD(4) antagonists is presented. The key diarylpropane framework was prepared by Claisen-Schmidt condensation and selective reduction of the enone. Depending on the bridge to the 7-chloroquinaldine moiety, alkylation or Heck coupling methodology was developed. The chiral sulfides were introduced by asymmetric reduction of the diarylpropanone intermediates and subsequent inversion of the chiral center.

  DOI：

  10.1021/jo952103j

文献信息

• Practical Route to a New Class of LTD₄ Receptor Antagonists
  作者：Robert D. Larsen、Edward G. Corley、Anthony O. King、James D. Carroll、Paul Davis、Thomas R. Verhoeven、Paul J. Reider、Marc Labelle、Jacques Y. Gauthier、Yi Bin Xiang、Robert J. Zamboni

  DOI：10.1021/jo952103j

  日期：1996.1.1

  A general approach to the synthesis of a new class of LTD(4) antagonists is presented. The key diarylpropane framework was prepared by Claisen-Schmidt condensation and selective reduction of the enone. Depending on the bridge to the 7-chloroquinaldine moiety, alkylation or Heck coupling methodology was developed. The chiral sulfides were introduced by asymmetric reduction of the diarylpropanone intermediates and subsequent inversion of the chiral center.