(2Z,4Z,6E)-methyl 7-(3-chlorophenyl)-6-formyl-3-phenylhepta-2,4,6-trienoate | 1355676-98-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2Z,4Z,6E)-methyl 7-(3-chlorophenyl)-6-formyl-3-phenylhepta-2,4,6-trienoate
• CAS: 1355676-98-0
• 化学式: C₂₁H₁₇ClO₃
• 分子量: 352.817
• InChiKey: DTENGGDVPDPMPU-LXNOVCHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2Z,4Z,6E)-methyl 7-(3-chlorophenyl)-6-formyl-3-phenylhepta-2,4,6-trienoate 在 (-)-(5aS,10bR)-5a,10b-二氢-2-(2,4,6-三甲基苯基)-4H,6H-茚并[2,1-b][1,2,4]三唑[4,3-d][1,4]氯化恶唑鎓一水合物 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 以74%的产率得到(S,E)-methyl 2-(4-(3-chlorobenzylidene)-5-oxo-1-phenylcyclopent-2-enyl)acetate
  参考文献：
  名称：

  Highly Enantioselective Cyclizations of Conjugated Trienes with Low Catalyst Loadings: A Robust Chiral N-Heterocyclic Carbene Enabled by Acetic Acid Cocatalyst

  摘要：

  Densely functionalized cyclopentenones are useful synthetic intermediates. We report herein a new method to synthesize this important class of compounds through a highly enantioselective (98 -> 99% ee) triene cyclization that is cocatalyzed by acetic acid and a chiral N-heterocyclic carbene (NHC). We discovered that acetic acid not only could coexist with NHCs but also could greatly stabilize the active catalyst, which enables a long-lived catalyst with high reactivity and selectivity.

  DOI：

  10.1021/ol203375y
• 作为产物：
  描述：

  (Z)-1-chloro-3-(3,3-diethoxy-2-iodoprop-1-enyl)benzene 在 盐酸 、 正丁基锂 、 水 作用下， 以 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 8.34h， 生成 (2Z,4Z,6E)-methyl 7-(3-chlorophenyl)-6-formyl-3-phenylhepta-2,4,6-trienoate
  参考文献：
  名称：

  Highly Enantioselective Cyclizations of Conjugated Trienes with Low Catalyst Loadings: A Robust Chiral N-Heterocyclic Carbene Enabled by Acetic Acid Cocatalyst

  摘要：

  Densely functionalized cyclopentenones are useful synthetic intermediates. We report herein a new method to synthesize this important class of compounds through a highly enantioselective (98 -> 99% ee) triene cyclization that is cocatalyzed by acetic acid and a chiral N-heterocyclic carbene (NHC). We discovered that acetic acid not only could coexist with NHCs but also could greatly stabilize the active catalyst, which enables a long-lived catalyst with high reactivity and selectivity.

  DOI：

  10.1021/ol203375y