(2Z,4E)-2-benzylidene-4-methyl-1-[(S)-2-oxo-4-phenyloxazolidin-3-yl]hex-4-ene-1,3-dione | 608533-36-4

• 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,4E)-2-benzylidene-4-methyl-1-[(S)-2-oxo-4-phenyloxazolidin-3-yl]hex-4-ene-1,3-dione
• 英文别名: (E,2Z)-2-benzylidene-4-methyl-1-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]hex-4-ene-1,3-dione
• CAS: 608533-36-4
• 化学式: C₂₃H₂₁NO₄
• 分子量: 375.424
• InChiKey: TYZXUFCFMLLINF-PQZNGZCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-2-benzylidene-4-methyl-1-[(S)-2-oxo-4-phenyloxazolidin-3-yl]hex-4-ene-1,3-dione 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(S)-3-[(1S,5S)-3,4-dimethyl-2-oxo-5-phenylcyclopent-3-enecarbonyl]-4-phenyloxazolidin-2-one
  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：

  tigloyl chloride 、 (4S)-3-(3-phenyl-2-propyonyl)-4-phenyloxazolidin-2-one 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88%的产率得到(2Z,4E)-2-benzylidene-4-methyl-1-[(S)-2-oxo-4-phenyloxazolidin-3-yl]hex-4-ene-1,3-dione
  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.