2-phenyl-2,3-dihydrobenzo[e]1,4-oxathiepin-5-one

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-phenyl-2,3-dihydrobenzo[e]1,4-oxathiepin-5-one
• 英文别名: 2,3-dihydro-2-phenylbenzo[e][1,4]-oxathiepin-5-one；2-Phenyl-2,3-dihydro-4,1-benzoxathiepin-5-one
• 化学式: C₁₅H₁₂O₂S
• 分子量: 256.325
• InChiKey: CISIBUCKESAJIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 、 硫代水杨酸 在 溴化二甲基溴化锍 作用下， 反应 2.0h， 以93%的产率得到2-phenyl-2,3-dihydrobenzo[e]1,4-oxathiepin-5-one
  参考文献：
  名称：

  (Bromodimethyl)sulfonium Bromide–Mediated Thiolysis of Epoxides: An Easy Access to β-Hydroxy Sulfides and Benzoxathiepinones in Solvent-Free Conditions

  摘要：

  A mild, rapid and highly regioselective opening of epoxides by mercaptans to -hydroxy sulfides and benzoxathiepinones has been achieved in excellent yields, using catalytic amount of (bromodimethyl)sulfonium bromide in solvent free reaction conditions.

  DOI：

  10.1080/00397910903458595

文献信息

• Benzodiazepine analogues. Part 21.13C NMR analysis of benzoxathiepine derivatives
  作者：Aifheli C. Gelebe、Perry T. Kaye、Rosalyn Klein、Joyce D. Sewry、Andrew G. Soper

  DOI：10.1002/mrc.1649

  日期：2005.11

  The influence of substituents and structure on the 13C NMR spectra of four series of benzoxathiepine derivatives has been investigated. Signal assignments in the 13C NMR spectra have been facilitated by the use of several predictive methods, permitting comparison of their relative efficacy. Copyright © 2005 John Wiley & Sons, Ltd.

  已经研究了取代基和结构对四个系列的苯并氧杂噻吩衍生物的 13C NMR 谱的影响。使用几种预测方法促进了 13C NMR 光谱中的信号分配，允许比较它们的相对功效。版权所有 © 2005 John Wiley & Sons, Ltd.
• Benzodiazepine Analogues. Part 15.¹Synthesis of Benzoxathiepine Derivatives
  作者：Aifheli C. Gelebe、Perry T. Kaye

  DOI：10.1080/00397919608003848

  日期：1996.12

  Abstract Stepwise cyclisation sequences have provided access to a series of novel 4-phenyl-3, 4-dihydro-1,5-benzoxathiepine-2-ones and 2-and 3-phenyl-4, 1-benzoxathiepine analogues.

  摘要逐步环化序列提供了获得一系列新型 4-phenyl-3, 4-dihydro-1,5-benzoxathiepine-2-ones 和 2-和 3-phenyl-4, 1-benzoxathiepine 类似物的途径。
• One-Pot Synthesis of Benzo[<i>e</i>]1,4-oxathiepin-5-ones under Solvent-Free Condition via Self-Promoted Thiolysis of 1,2-Epoxides
  作者：Francesco Fringuelli、Ferdinando Pizzo、Simone Tortoioli、Luigi Vaccaro

  DOI：10.1021/jo0487496

  日期：2004.12.1

  Under solvent-free conditions, thiosalicylic acid (2) efficiently self-promotes the thiolysis of 1,2-epoxides 1, anti-stereoselectively and generally totally beta-regioselectively. The resulting beta-hydroxysulfide products 3 have been obtained in very good yields. Benzo[e]1,4-oxathiepin-5-ones 4 have been easily prepared in a regio- and diasteroselective manner and in satisfactory yields under SFC by a one-pot protocol including nucleophilic ring opening of 1,2-epoxides 1 by thiosalicylic acid (2) and thermally induced lactonization of beta-hydroxy arylsulfides 3. Solvent-free condition and the absence of any catalyst make this procedure atom-economical and environmentally friendly.
• (Bromodimethyl)sulfonium Bromide–Mediated Thiolysis of Epoxides: An Easy Access to β-Hydroxy Sulfides and Benzoxathiepinones in Solvent-Free Conditions
  作者：M. Shailaja、A. Manjula、B. Vittal Rao

  DOI：10.1080/00397910903458595

  日期：2010.11.16

  A mild, rapid and highly regioselective opening of epoxides by mercaptans to -hydroxy sulfides and benzoxathiepinones has been achieved in excellent yields, using catalytic amount of (bromodimethyl)sulfonium bromide in solvent free reaction conditions.