2-(dec-1-yn-1-yl)benzo[d][1,3]oxathiole | 1448898-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Benzoxathioles
• 英文名称: 2-(dec-1-yn-1-yl)benzo[d][1,3]oxathiole
• 英文别名: 2-Dec-1-ynyl-1,3-benzoxathiole；2-dec-1-ynyl-1,3-benzoxathiole
• CAS: 1448898-44-9
• 化学式: C₁₇H₂₂OS
• 分子量: 274.427
• InChiKey: LAQBWKJHDQQYCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-羟基苯硫酚 在 lithium perchlorate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 11.0h， 生成 2-(dec-1-yn-1-yl)benzo[d][1,3]oxathiole
  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

• 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.