2-phenethyl-1,3-oxathiolane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenethyl-1,3-oxathiolane
• 英文别名: 2-(2-Phenylethyl)-1,3-oxathiolane
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: CMKDTLRVPKAWTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenethyl-1,3-oxathiolane 在 eosin Y disodium salt 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以59%的产率得到苯丙醛
  参考文献：
  名称：

  Visible light photoredox catalyzed deprotection of 1,3-oxathiolanes

  摘要：

  公开了一种温和且有效的可见光光氧化还原催化空气氧化的1,3-氧硫杂环戊烷去保护方法，使用曙红Y作为光催化剂。

  DOI：

  10.1039/c9ob02517k
• 作为产物：
  描述：

  苯丙醛 、 2-巯基乙醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 生成 2-phenethyl-1,3-oxathiolane
  参考文献：
  名称：

  Visible light photoredox catalyzed deprotection of 1,3-oxathiolanes

  摘要：

  公开了一种温和且有效的可见光光氧化还原催化空气氧化的1,3-氧硫杂环戊烷去保护方法，使用曙红Y作为光催化剂。

  DOI：

  10.1039/c9ob02517k

文献信息

• Amberlyst® 15 as a Mild, Chemoselective and Reusable Heterogeneous Catalyst for the Conversion of Carbonyl Compounds to 1,3-Oxathiolanes
  作者：Roberto Ballini、Giovanna Bosica、Raimondo Maggi、Alessandro Mazzacani、Paolo Righi、Giovanni Sartori

  DOI：10.1055/s-2001-17532

  日期：——

  Conversion of Carbonyl Compounds to 1,3-Oxathiolanes R berto Ballini,*a Giovanna Bosica,a Raimondo Maggi,*b Alessandro Mazzacani,b Paolo Righi,c Giovanni Sartorib a Dipartimento di Scienze Chimiche dell'Università, Via S. Agostino 1, 62032 Camerino (MC), Italy b Dipartimento di Chimica Organica e Industriale dell'Università, Parco Area delle Scienze 17A, 43100 Parma, Italy c Dipartimento di Chimica

  羰基化合物转化为 1,3-氧硫杂环戊烷 R berto Ballini,*a Giovanna Bosica,a Raimondo Maggi,*b Alessandro Mazzacani,b Paolo Righi,c Giovanni Sartorib a Dipartimento di Scienze Chimiche dell'Università, Via S. Agostino 1, 62032 Camerino (MC), Italy b Dipartimento di Chimica Organica e Industriale dell'Università, Parco Area delle Scienze 17A, 43100 Parma, Italy c Dipartimento di Chimica Organica 'A. Mangini' dell'Università
• Silica Gel-Supported Polyphosphoric Acid (PPA/SiO₂) as an Efficient and Reusable Catalyst for Conversion of Carbonyl Compounds into Oxathioacetals and Dithioacetals
  作者：Tadashi Aoyama、Toshio Takido、Mitsuo Kodomari

  DOI：10.1055/s-2004-832812

  日期：——

  A simple and efficient method for the conversion of carbonyl compounds to oxathioacetals and dithioacetals by using polyphosphoric acid supported on silica gel (PPA/SiO2) as an acid catalyst have been developed. PPA/SiO2 is easily recovered from the reaction mixture and reused without a decrease in catalytic ­activity.

  开发了一种简单高效的方法，通过使用负载在硅胶上的多磷酸（PPA/SiO2）作为酸催化剂，将羰基化合物转化为氧硫酯和二硫酯。PPA/SiO2可以轻松从反应混合物中回收，并且在重复使用时没有催化活性下降。
• Melamine Trisulfonic Acid as a New, Efficient and Reusable Catalyst for the Chemoselective Oxathioacetalyzation of Aldehydes
  作者：F. Shirini、J. Albadi

  DOI：10.5012/bkcs.2010.31.5.1119

  日期：2010.5.20

  following dissadvan-tages: harsh reaction conditions, long reaction times, low yields, use of corrosive, expensive or moisture-sensitive reagents, destruction of the catalyst in work-up procedure, special efforts require to prepare the catalysts and tedious work-up procedure. Therefore, there is a scope to develop an alternative method for the protection of aldehydes as 1,3-oxathiolanes.In recent years,

  然而，这些程序中的许多都具有以下一个或多个缺点：苛刻的反应条件、反应时间长、产率低、使用腐蚀性、昂贵或对水分敏感的试剂、在后处理过程中破坏催化剂，需要特别努力来准备催化剂和繁琐的后处理程序。因此，开发一种替代方法来保护醛类作为1,3-氧杂硫杂环戊烷是有空间的。近年来，引入用于官能团转化的新试剂，成为我们研究计划的重要组成部分。
• Efficient regeneration of aldehydes from their corresponding 1,3-oxathiolanes in the absence of solvent
  作者：Farhad Shirini、Seyyedeh Kobra Mirhashemi、Aysa Pourvali、Masoumeh Abedini

  DOI：10.1016/j.cclet.2010.10.034

  日期：2011.4

  A mild and efficient method for the oxidative deprotection of 1,3-oxathiolanes with Fe(NO3)(3)center dot 9H(2)O and Cu(NO3)(2)center dot 3H(2)O in the absence of solvent is reported. (C) 2010 Farhad Shirini. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Tantalum(V) Chloride–Silica Gel: An Efficient Catalyst for Conversion of Carbonyl Compounds to 1,3‐Oxathiolanes
  作者：S. Chandrasekhar、S. Jaya Prakash、T. Shyamsunder、T. Ramachandar

  DOI：10.1080/00397910500282588

  日期：2005.12.1

  A variety of carbonyl compounds can be easily converted to the corresponding 1,3-oxathiolanes in the presence of a catalytic amount of tantalum(V) chloride [TaCl5] on silica gel in dichloromethane. Mild reaction conditions, efficiency, high yields, operational simplicity, and only 2.5 mol% of TaCl5 catalyst are some of the major advantages of the procedure.