(2R,3S,Z)-6-(4-(3-bromobenzyloxy)benzylidene)-3,4-dimethyl-2-phenyl-1,4-oxazepane-5,7-dione | 1237025-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3S,Z)-6-(4-(3-bromobenzyloxy)benzylidene)-3,4-dimethyl-2-phenyl-1,4-oxazepane-5,7-dione
• 英文别名: (2R,3S,6Z)-6-[[4-[(3-bromophenyl)methoxy]phenyl]methylidene]-3,4-dimethyl-2-phenyl-1,4-oxazepane-5,7-dione
• CAS: 1237025-10-3
• 化学式: C₂₇H₂₄BrNO₄
• 分子量: 506.396
• InChiKey: RJICYRVVSLINHM-FYJLZVTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,Z)-6-(4-(3-bromobenzyloxy)benzylidene)-3,4-dimethyl-2-phenyl-1,4-oxazepane-5,7-dione 、 1-丙炔溴化镁 在 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(2R,3S)-6-((S)-1-(4-(3-bromobenzyloxy)phenyl)but-2-ynyl)-3,4-dimethyl-2-phenyl-1,4-oxazepane-5,7-dione
  参考文献：
  名称：

  Asymmetric syntheses of a GPR40 receptor agonist via diastereoselective and enantioselective conjugate alkynylation

  摘要：

  Two asymmetric methods to synthesize a potent GPR40 receptor agonist are reported. Both synthetic routes utilize readily available, inexpensive starting materials and reagents. The first route relies on a highly diastereoselective conjugate alkynylation of an ephedrine-derived oxazepanedione acceptor. The second route features the enantioselective alkynylation of a Meldrum's acid-derived acceptor mediated by a chiral zinc cinchonidine reagent. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.019
• 作为产物：
  描述：

  (2R,3S)-6-(4-(3-bromobenzyloxy)benzylidene)-3,4-dimethyl-2-phenyl-1,4-oxazepane-5,7-dione 以 异丙醇 为溶剂， 反应 4.5h， 以1.81 g的产率得到(2R,3S,Z)-6-(4-(3-bromobenzyloxy)benzylidene)-3,4-dimethyl-2-phenyl-1,4-oxazepane-5,7-dione
  参考文献：
  名称：

  Asymmetric syntheses of a GPR40 receptor agonist via diastereoselective and enantioselective conjugate alkynylation

  摘要：

  Two asymmetric methods to synthesize a potent GPR40 receptor agonist are reported. Both synthetic routes utilize readily available, inexpensive starting materials and reagents. The first route relies on a highly diastereoselective conjugate alkynylation of an ephedrine-derived oxazepanedione acceptor. The second route features the enantioselective alkynylation of a Meldrum's acid-derived acceptor mediated by a chiral zinc cinchonidine reagent. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.019