ethyl (2Z)-2-(1-benzyl-1H-pyrrole-2-carbonyl)-4-methylpent-2-enoate | 1252611-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2Z)-2-(1-benzyl-1H-pyrrole-2-carbonyl)-4-methylpent-2-enoate
• 英文别名: ethyl (Z)-2-(1-benzylpyrrole-2-carbonyl)-4-methylpent-2-enoate
• CAS: 1252611-97-4
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: BLMPDSUJMUKOKD-LGMDPLHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-2-(1-benzyl-1H-pyrrole-2-carbonyl)-4-methylpent-2-enoate 生成 ethyl (2E)-2-(1-benzyl-1H-pyrrole-2-carbonyl)-4-methylpent-2-enoate
  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
• 作为产物：
  描述：

  ethyl 4-methylpent-2-ynoate 、 1-benzyl-1H-pyrrole-2-carbonyl chloride 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82%的产率得到ethyl (2Z)-2-(1-benzyl-1H-pyrrole-2-carbonyl)-4-methylpent-2-enoate
  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.