(2E,4Z,6E)-methyl 7-(3-chlorophenyl)-6-formyl-3,5-dimethylhepta-2,4,6-trienoate | 1355676-93-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (2E,4Z,6E)-methyl 7-(3-chlorophenyl)-6-formyl-3,5-dimethylhepta-2,4,6-trienoate
• 英文别名: methyl (2E,4Z,6E)-7-(3-chlorophenyl)-6-formyl-3,5-dimethylhepta-2,4,6-trienoate
• CAS: 1355676-93-5
• 化学式: C₁₇H₁₇ClO₃
• 分子量: 304.773
• InChiKey: SBHGMKPPFPJTKX-NJCVAPCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,4Z,6E)-methyl 7-(3-chlorophenyl)-6-formyl-3,5-dimethylhepta-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 、 C₂₁H₂₂N₃O⁽¹⁺⁾*Cl^(1-) 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 生成 (E)-methyl 2-(4-(3-chlorobenzylidene)-1,3-dimethyl-5-oxocyclopent-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：

  methyl (E)-3-formylcrotonate 在 盐酸 、 正丁基锂 、 水 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 8.59h， 生成 (2E,4Z,6E)-methyl 7-(3-chlorophenyl)-6-formyl-3,5-dimethylhepta-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