2-methyl-2-p-tolyl-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-methyl-2-p-tolyl-1,3-oxathiolane
• 英文别名: 1,3-Oxathiolane, 2-methyl-2-(4-methylphenyl)-；2-methyl-2-(4-methylphenyl)-1,3-oxathiolane
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: GOTUTVQKHSPAEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 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-methyl-2-p-tolyl-1,3-oxathiolane 在 C₄₈H₂₄N₄O₈^(6-)*1.5C₁₀H₈N₂*3C₃H₇NO*4H₂O*3Zn⁽²⁺⁾ 、 氧气 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 对甲基苯乙酮
  参考文献：
  名称：

  Zn(ii) porphyrin based nano-/microscale metal–organic frameworks: morphology dependent sensitization and photocatalytic oxathiolane deprotection

  摘要：

  Zn(II)卟啉基纳米/微尺度金属有机框架（MOFs）显示出形态依赖的¹O₂敏化效率，并作为选择性光催化剂用于氧杂硫环烷基的保护基去除。

  DOI：

  10.1039/c6ra01599a
• 作为产物：
  描述：

  对甲基苯乙酮 、 2-巯基乙醇 在 tetra-N-butylammonium tribromide 、 原甲酸三甲酯 作用下， 生成 2-methyl-2-p-tolyl-1,3-oxathiolane
  参考文献：
  名称：

  Deprotection of 1,3-oxathiolanes to ketones promoted by base

  摘要：

  A variety of 1,3-oxathiolanes can be easily converted to the corresponding ketones in good yields with LTMP in THF. This deprotection methodology shows satisfactory chemoselectivity when other protecting groups, such as dimethylketal, 1,3-dioxolane, 1,3-dithiane, and other acid-sensitive groups, are present within the same substrates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.053

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。
• Zn(<scp>ii</scp>) porphyrin based nano-/microscale metal–organic frameworks: morphology dependent sensitization and photocatalytic oxathiolane deprotection
  作者：Fang-Yao Zhao、Wen-Juan Li、An Guo、Lan Chang、Yue Li、Wen-Juan Ruan

  DOI：10.1039/c6ra01599a

  日期：——

  Zn(ii) porphyrin based nano-/microscale MOFs showed morphology dependent ¹O₂ sensitization efficiency and were used as selective photocatalysts for oxathiolane deprotection.

  Zn(II)卟啉基纳米/微尺度金属有机框架（MOFs）显示出形态依赖的¹O₂敏化效率，并作为选择性光催化剂用于氧杂硫环烷基的保护基去除。

• Deprotection of 1,3-oxathiolanes to ketones promoted by base
  作者：Biao Du、Changchun Yuan、Langzhong Zhang、Li Yang、Bo Liu

  DOI：10.1016/j.tetlet.2013.02.053

  日期：2013.5

  A variety of 1,3-oxathiolanes can be easily converted to the corresponding ketones in good yields with LTMP in THF. This deprotection methodology shows satisfactory chemoselectivity when other protecting groups, such as dimethylketal, 1,3-dioxolane, 1,3-dithiane, and other acid-sensitive groups, are present within the same substrates. (C) 2013 Elsevier Ltd. All rights reserved.
• Nickel boride mediated cleavage of 1,3-oxathiolanes: a convenient approach to deprotection and reduction
  作者：Jitender M. Khurana、Devanshi Magoo、Kiran Dawra

  DOI：10.1007/s00706-015-1608-3

  日期：2016.6

  cleaved by nickel boride allowing regeneration of corresponding carbonyl compounds. Optimum reaction conditions have also been defined to obtain alcohols exclusively by reduction of oxathiolanes. Reactions are rapid at room temperature and do not require protection from atmosphere. Mild reaction conditions, simple work up, and high yields are some of the major advantages of the procedure. Graphical

  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
• Silica-Gel Supported Sulfamic Acid (SA/SiO₂) as an Efficient and Reusable Catalyst for Conversion of Ketones into Oxathioacetals and Dithioacetals
  作者：Tadashi Aoyama、Toshihiko Suzuki、Takashi Nagaoka、Toshio Takido、Mitsuo Kodomari

  DOI：10.1080/00397911.2011.604458

  日期：2013.1.1

  A simple and efficient method for the conversion of carbonyl compounds to oxathioacetals and dithioacetals using SA/SiO2 as an acid catalyst has been achieved. SA/SiO2 is easily recovered from the reaction mixture and can be reused at least 15 times without loss of catalytic activity.