2-styryl-1,3-oxathiolane | 113124-71-3

• 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-styryl-1,3-oxathiolane
• 英文别名: (E)-2-styryl-1,3-oxathiolane；2-[(E)-2-phenylethenyl]-1,3-oxathiolane
• CAS: 113124-71-3
• 化学式: C₁₁H₁₂OS
• 分子量: 192.282
• InChiKey: QFCNKEIVVAVKOA-VOTSOKGWSA-N

物化性质

• 沸点：
  321.2±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-styryl-1,3-oxathiolane 在 三氟甲磺酸三甲基硅酯 对硝基苯甲醛 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以75%的产率得到反式肉桂醛
  参考文献：
  名称：

  Unusually facile oxathioacetal transfer reaction: an efficient, highly selective catalytic deprotection protocol

  摘要：

  在4-硝基苯甲醛存在下，以CF3SO3SiMe3为催化剂，可在室温下高效进行氧硫缩醛的一对一交换反应，转化为羰基化合物。该开发的方法提供了在硫缩醛存在下的氧硫缩醛选择性且有效的去保护。

  DOI：

  10.1039/c39940001937
• 作为产物：
  描述：

  肉桂醛 在 aminopropylated silica gel hydrochloride 、 原甲酸三甲酯 作用下， 以 甲醇 为溶剂， 生成 2-styryl-1,3-oxathiolane
  参考文献：
  名称：

  Synthesis of α,β-unsaturated oxathiolanes

  摘要：

  The formation of alpha,beta-unsaturated oxathiolanes 2 from alpha,beta-unsaturated carbonyl derivatives was achieved selectively and in high yields using the heterogeneous catalyst APSG(.)HCI. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01428-x

文献信息

• LiBF₄ Catalyzed Chemoselective Conversion of Aldehydes to 1,3-Oxathiolanes and 1,3-Dithianes
  作者：J. S. Yadav、B. V. S. Reddy、Sushil Kumar Pandey

  DOI：10.1055/s-2001-10780

  日期：——

  Lithium tetrafluoroborate is found to be an efficient catalyst for the chemoselective protection of both aromatic and aliphatic aldehydes as 1,3-oxathiolanes and 1,3-dithianes under mild reaction conditions. Due to the neutral reaction conditions, this method is compatible with acid sensitive substrates.

  四氟硼酸锂被发现是一种高效的催化剂，可以在温和的反应条件下对芳香醛和脂肪醛进行化学选择性保护，生成1,3-氧硫环烷和1,3-二硫烷。由于反应条件中性，这种方法与酸敏感底物相容。
• Molten Salt as a Green Reaction Medium: Efficient and Chemoselective Dithioacetalization and Oxathioacetalization of Aldehydes Mediated by Molten Tetrabutylammonium Bromide
  作者：Brindaban C. Ranu、Arijit Das

  DOI：10.1071/ch03318

  日期：——

  Tetrabutylammonium bromide in the molten state has been demonstrated to be a very efficient catalyst and reaction medium for the highly chemoselective dithioacetalization and oxathioacetalization of aldehydes. The tetrabutylammonium bromide is recycled for subsequent reactions.

  熔融状态的四丁基溴化铵已被证明是一种非常有效的催化剂和反应介质，可用于醛的高化学选择性二硫代缩醛化和氧硫代缩醛化。四丁基溴化铵被循环用于后续反应。
• 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
• Indium Trifluoromethanesulfonate as a Mild and Chemoselective Catalyst for the Conversion of Carbonyl Compounds into 1,3-Oxathiolanes
  作者：Tsuneo Sato、Kiyoshi Kazahaya、Nao Hamada、Shinya Ito

  DOI：10.1055/s-2002-33541

  日期：——

  An efficient method for the preparation of 1,3-oxathiolanes from aldehydes and ketones with 2-mercaptoethanol in the presence of a catalytic amount of indium trifluoromethanesulfonate is reported.

  报道了在催化量的三氟甲磺酸铟存在下，用 2-巯基乙醇从醛和酮制备 1,3-氧杂硫杂环戊烷的有效方法。
• Visible light photoredox catalyzed deprotection of 1,3-oxathiolanes
  作者：Mingyang Yang、Zhimin Xing、Bowen Fang、Xingang Xie、Xuegong She

  DOI：10.1039/c9ob02517k

  日期：——

  A mild and efficient visible light photoredox catalyzed aerobic deprotection of 1,3-oxathiolanes using Eosin Y as a photocatalyst is disclosed.

  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。