(2S)-2-prop-2-enyl-3,4-dihydro-2H-chromene | 190789-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2S)-2-prop-2-enyl-3,4-dihydro-2H-chromene
• CAS: 190789-94-7
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: APGBWCFMEQMILE-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S)-2-prop-2-enyl-3,4-dihydro-2H-chromene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以81%的产率得到(R)-2-propylchromane
  参考文献：
  名称：

  Bimolecular coupling reactions through oxidatively generated aromatic cations: scope and stereocontrol

  摘要：

  Chromenes, isochromenes, and benzoxathioles react with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form stable aromatic cations that react with a range of nucleophiles. These oxidative fragment coupling reactions provide rapid access to structurally diverse heterocycles. Conducting the reactions in the presence of a chiral Bronsted acid results in the formation of an asymmetric ion pair that can provide enantiomerically enriched products in a rare example of a stereoselective process resulting from the generation of a chiral electrophile through oxidative carbon hydrogen bond cleavage. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.011
• 作为产物：
  描述：

  3-(2-溴苯基)丙酸甲酯 在 palladium diacetate 、 二异丁基氢化铝 、 caesium carbonate 、 (+)-二异松蒎基氯硼烷 、 2-(二叔丁基膦)联苯 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.58h， 生成 (2S)-2-prop-2-enyl-3,4-dihydro-2H-chromene
  参考文献：
  名称：

  Bimolecular coupling reactions through oxidatively generated aromatic cations: scope and stereocontrol

  摘要：

  Chromenes, isochromenes, and benzoxathioles react with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form stable aromatic cations that react with a range of nucleophiles. These oxidative fragment coupling reactions provide rapid access to structurally diverse heterocycles. Conducting the reactions in the presence of a chiral Bronsted acid results in the formation of an asymmetric ion pair that can provide enantiomerically enriched products in a rare example of a stereoselective process resulting from the generation of a chiral electrophile through oxidative carbon hydrogen bond cleavage. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.011

文献信息

• US5925662A
  申请人：——

  公开号：US5925662A

  公开（公告）日：1999-07-20
• Bimolecular coupling reactions through oxidatively generated aromatic cations: scope and stereocontrol
  作者：Yubo Cui、Louis A. Villafane、Dane J. Clausen、Paul E. Floreancig

  DOI：10.1016/j.tet.2013.05.011

  日期：2013.9

  Chromenes, isochromenes, and benzoxathioles react with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form stable aromatic cations that react with a range of nucleophiles. These oxidative fragment coupling reactions provide rapid access to structurally diverse heterocycles. Conducting the reactions in the presence of a chiral Bronsted acid results in the formation of an asymmetric ion pair that can provide enantiomerically enriched products in a rare example of a stereoselective process resulting from the generation of a chiral electrophile through oxidative carbon hydrogen bond cleavage. (C) 2013 Elsevier Ltd. All rights reserved.