methyl (E)-4-oxo-3-phenylbut-2-enoate | 1355677-91-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-4-oxo-3-phenylbut-2-enoate
• CAS: 1355677-91-6
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: TVLFNBMCMGGBFC-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  methyl (E)-4-oxo-3-phenylbut-2-enoate 、 碘甲基-三苯基-碘化磷 在 sodium hexamethyldisilazane 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 生成 (2Z,4Z)-methyl 5-iodo-3-phenylpenta-2,4-dienoate 、 (2Z,4E)-methyl 5-iodo-3-phenylpenta-2,4-dienoate
  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

文献信息

• Highly Enantioselective Cyclizations of Conjugated Trienes with Low Catalyst Loadings: A Robust Chiral <i>N</i>-Heterocyclic Carbene Enabled by Acetic Acid Cocatalyst
  作者：Guansai Liu、Phillip D. Wilkerson、Christopher A. Toth、Hao Xu

  DOI：10.1021/ol203375y

  日期：2012.2.3

  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.