(E)-3-phenyl-2-(3,4,5-trimethoxybenzoyl)-2-propenal

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-phenyl-2-(3,4,5-trimethoxybenzoyl)-2-propenal
• 英文别名: (E)-3-phenyl-2-(3,4,5-trimethoxybenzoyl)prop-2-enal
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: RMJCQDHVTHOOPH-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-phenyl-2-(3,4,5-trimethoxybenzoyl)-2-propenal 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  Kerr, Daniel J.; Metje, Christiane; Flynn, Bernard L., Chemical Communications, 2003, # 12, p. 1380 - 1381

  摘要：

  DOI：
• 作为产物：
  描述：

  苯丙炔醛 、 3,4,5-三甲氧基苯甲酰氯 在 四(三苯基膦)钯 、 三正丁基氢锡 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到(E)-3-phenyl-2-(3,4,5-trimethoxybenzoyl)-2-propenal
  参考文献：
  名称：

  A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric Synthesis of Five-Membered Carbocycles

  摘要：

  Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille-Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.

  DOI：

  10.1021/jo100736p

文献信息

• A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric Synthesis of Five-Membered Carbocycles
  作者：Daniel J. Kerr、Jonathan M. White、Bernard L. Flynn

  DOI：10.1021/jo100736p

  日期：2010.11.5

  Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille-Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.
• Kerr, Daniel J.; Metje, Christiane; Flynn, Bernard L., Chemical Communications, 2003, # 12, p. 1380 - 1381
  作者：Kerr, Daniel J.、Metje, Christiane、Flynn, Bernard L.

  DOI：——

  日期：——