5-chloro-2-[(3R)-3-hydroxy-3-(3-hydroxyphenyl)propyl]-N,N-dimethylbenzamide | 177747-97-6

• 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-[(3R)-3-hydroxy-3-(3-hydroxyphenyl)propyl]-N,N-dimethylbenzamide
• CAS: 177747-97-6
• 化学式: C₁₈H₂₀ClNO₃
• 分子量: 333.815
• InChiKey: BRBFWNFLAGEUNG-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-2-[(3R)-3-hydroxy-3-(3-hydroxyphenyl)propyl]-N,N-dimethylbenzamide 、 7-Chloro-2-chloromethyl-quinoline; hydrochloride 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-chloro-2-[(3R)-3-[3-[(7-chloroquinolin-2-yl)methoxy]phenyl]-3-hydroxypropyl]-N,N-dimethylbenzamide
  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：

  5-chloro-2-[3-(3-hydroxyphenyl)-3-oxopropyl]benzoic acid methyl ester 在 dimethyl sulfide borane 、 乙基溴化镁 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 22.92h， 生成 5-chloro-2-[(3R)-3-hydroxy-3-(3-hydroxyphenyl)propyl]-N,N-dimethylbenzamide
  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