(2Z,3Z)-ethyl 2-benzylidene-4-iodobut-3-enoate | 1355677-97-2

• 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: (2Z,3Z)-ethyl 2-benzylidene-4-iodobut-3-enoate
• CAS: 1355677-97-2
• 化学式: C₁₃H₁₃IO₂
• 分子量: 328.15
• InChiKey: XZWBAOUQHOEIRM-DMGFJBLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-(3,3-diethoxy-2-iodoprop-1-enyl)benzene 、 (2Z,3Z)-ethyl 2-benzylidene-4-iodobut-3-enoate 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,3Z,5E)-ethyl 2-benzylidene-5-formyl-6-phenylhexa-3,5-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
• 作为产物：
  描述：

  碘甲基-三苯基-碘化磷 、 (Z)-ethyl 2-formyl-3-phenyl-2-propeonate 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， 以69%的产率得到(2Z,3Z)-ethyl 2-benzylidene-4-iodobut-3-enoate
  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