2-(4-tolyl)-1,3-oxathiolane | 22391-04-4

• 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-(4-tolyl)-1,3-oxathiolane
• 英文别名: 2-(4-methylphenyl)-1,3-oxathiolane
• CAS: 22391-04-4
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: ILFTUQCCIXBMTD-UHFFFAOYSA-N

物化性质

• 沸点：
  125 °C(Press: 1 Torr)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-(4-tolyl)-1,3-oxathiolane 在 甲醇 、 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 反应 1.5h， 以89%的产率得到对甲基苯甲醛
  参考文献：
  名称：

  硼化镍介导的1,3-氧杂硫杂环戊烷的裂解：脱保护和还原的便捷方法

  摘要：

  摘要1,3-氧杂硫杂环戊烷被硼化镍快速裂解，从而允许相应的羰基化合物再生。还已经定义了最佳反应条件，以仅通过还原硫杂硫杂环戊烷获得醇。在室温下反应迅速，不需要保护气氛。温和的反应条件，简单的后处理和高收率是该方法的一些主要优点。 图形概要

  DOI：

  10.1007/s00706-015-1608-3
• 作为产物：
  描述：

  2-(4-甲基苯基)-1,3-二氧戊环 、 2-巯基乙醇 在 Fe(CF₃SO₃)3 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以94%的产率得到2-(4-tolyl)-1,3-oxathiolane
  参考文献：
  名称：

  Facile protection of carbonyl compounds as oxathiolanes and transoxathioacetalization of oxyacetals promoted by iron(III) trifluoroacetate or trifluoromethanesulfonate as chemoselective and recyclable catalysts

  摘要：

  Oxathioacetalization of carbonyl compounds and transoxathioacetalization of O,O-acetals/ketals are reported under nearly neutral conditions promoted by iron(III) trifluoroacetate [Fe(CF3CO2)(3)] or trifluoromethanesulfonate [Fe(CF3SO3)(3)] as recyclable and highly efficient Lewis acid catalysts. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.04.002

文献信息

• 2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO), N-Bromosuccinimide (NBS) and Bromine as Efficient Catalysts for Dithioacetalization and Oxathioacetalization of Carbonyl Compounds and Transdithioacetalization Reactions
  作者：Nasser Iranpoor、Habib Firouzabadi、Hamid Reza Shaterian、M. A. Zolfigol

  DOI：10.1080/10426500211712

  日期：2002.5.1

  6-tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1,3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high

  使用 2,4,4,6-四溴-2,5-环己二烯酮 (TABCO)、N-溴代琥珀酰亚胺 (NBS) 和溴作为有效催化剂将羰基化合物转化为环状和无环二硫缩醛和 1,3-描述了在温和反应条件下的硫杂环戊烷。这些催化剂还用于在硫醇存在下以高产率有效地将缩醛、二缩醛、缩酮、酰基、烯胺、腙和肟转二硫缩醛。
• 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。
• New Applications of Solid Silica Chloride (SiO 2 -Cl) in Organic Synthesis. Efficient Preparation of Diacetals of 2,2-Bis(Hydroxymethyl)-1,3-propanediol from Different Substrates and Their Transthioacetalization Reactions. Efficient Regeneration of Carbonyl Compounds from Acetals and Acylals
  作者：Habib Firouzabadi、Nasser Iranpoor、Hassan Hazarkhani

  DOI：10.1080/10426500214879

  日期：2002.12.1

  application of solid silica chloride, an easily available and efficient catalyst for the preparation of diacetal of 2,2-bis-(hydroxymethyl)-1,3-propanediol from aldehydes, acetals, acylals, and oximes, is described. Transthioacetalization of diacetals of 2,2-bis-(hydroxymethyl)-1,3-propanediol into their corresponding 1,3-dithianes and 1,3-dithiolanes in the presence of silica chloride is presented. Efficient

  描述了固体氯化硅的新应用，它是一种易于获得且高效的催化剂，用于从醛、缩醛、酰基和肟制备 2,2-双-（羟甲基）-1,3-丙二醇的二缩醛。介绍了 2,2-双-（羟甲基）-1,3-丙二醇的二缩醛在氯化硅存在下转化为相应的 1,3-二噻烷和 1,3-二硫戊烷的转硫缩醛化反应。还描述了在该催化剂存在下羰基化合物从其相应的缩醛、缩酮、二缩醛和酰基的有效再生。
• Blue LED-Promoted Oxathiacetalization of Aldehydes and Ketones
  作者：You-Chen Liu、Daggula Mallikarjuna Reddy、Xin-An Chen、Yi-Chen Shieh、Chin-Fa Lee

  DOI：10.1002/ejoc.202000218

  日期：2020.5.10

  A visible‐light‐promoted oxathiacetalization of aldehydes and ketones with 2‐mercaptoethanol and 3‐mercaptopropan‐1‐ol in the presence of eosin Y as catalyst is described leading to the formation of 1,3‐oxathiolanes and 1,3‐oxathianes at ambient temperature and under metal‐free conditions. The solvent is playing vital role in the protection of carbonyl compounds with mercaptoalcohol.

  描述了在曙红Y的催化下，使用2-巯基乙醇和3-巯基丙烷-1-醇在可见光条件下促进醛和酮的乙二醛乙醛缩醛化反应，从而导致1,3-氧杂硫杂环戊烷和1,3-氧杂蒽环的形成环境温度和无金属条件下。溶剂在用巯基醇保护羰基化合物中起着至关重要的作用。
• Ytterbium(III) Triflate-Catalyzed Conversion of Carbonyl Compounds into 1,3-Oxathiolanes in Ionic Liquids
  作者：Shive Chauhan、Anil Kumar、Nidhi Jain、Sandeep Rana

  DOI：10.1055/s-2004-835642

  日期：——

  The reaction of carbonyl compounds with 2-mercapto­ethanol to prepare 1,3-oxathiolanes has been successfully carried out in ionic liquids using ytterbium(III) triflate as a catalyst. Yields of the products are high and the catalyst can be easily recovered and reused in this reaction.

  利用三氟甲磺酸镱(III)作为催化剂，在离子液体中成功地进行了羰基化合物与2-巯基乙醇反应制备1,3-噁二唑烷的过程。产物的收率较高，并且催化剂可以很容易地回收并在该反应中重复使用。