(p-tolylthio)methyl acetate | 52834-75-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (p-tolylthio)methyl acetate
• 英文别名: (4-Methylphenyl)sulfanylmethyl acetate
• CAS: 52834-75-0
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: YYVPXGDTHRHXLM-UHFFFAOYSA-N

物化性质

• 沸点：
  150 °C(Press: 12 Torr)
• 密度：
  1.13±0.1 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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (p-tolylthio)methyl acetate 在 双氧水 、 溶剂黄146 作用下， 生成 acetic acid-(toluene-4-sulfonylmethyl ester)
  参考文献：
  名称：

  Bredereck et al., Chemische Berichte, 1954, vol. 87, p. 784,787

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基茴香硫醚 在 硫酸 、 双氧水 作用下， 以 甲醇 、 异丙醇 为溶剂， 生成 (p-tolylthio)methyl acetate
  参考文献：
  名称：

  Enzyme-promoted kinetic resolution of acetoxymethyl aryl sulfoxides

  摘要：

  A simple and efficient method of the synthesis of enantiomerically enriched, unknown acetoxymethyl aryl sulfoxides has been developed which is based on an enzyme-catalyzed hydrolysis of racemic substrates under the kinetic resolution conditions. The hydrolysis was performed not only in a buffer solution but also in diisopropyl ether in the absence of the external water added to give in some cases the products with ee up to 98%. The enantioselectivity of both procedures was dependent on the enzyme used and the aryl substituent, being lower for p-tolyl than for phenyl. A comparative asymmetric synthesis based on the oxidation of the corresponding sulfides using chiral oxidizing reagent turned out to be inferior to the method described. Absolute configuration of the newly synthesized compounds was ascribed on the basis of CD spectra. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.04.016

文献信息

• Electrochemical Oxidation Enables Regioselective and Scalable α-C(sp³)-H Acyloxylation of Sulfides
  作者：Huamin Wang、Meng He、Yongli Li、Heng Zhang、Dali Yang、Masanari Nagasaka、Zongchao Lv、Zhipeng Guan、Yangmin Cao、Fengping Gong、Zhilin Zhou、Jingyun Zhu、Supravat Samanta、Abhishek Dutta Chowdhury、Aiwen Lei

  DOI：10.1021/jacs.1c00288

  日期：2021.3.10

  A highly selective, environmentally friendly, and scalable electrochemical protocol for the construction of α-acyloxy sulfides, through the synergistic effect of self-assembly-induced C(sp3)–H/O–H cross-coupling, is reported. It features exceptionally broad substrate scope, high regioselectivity, gram-scale synthesis, construction of complex molecules, and applicability to a variety of nucleophiles

  报道了一种通过自组装诱导的 C(sp 3 )-H/O-H 交叉偶联的协同效应构建 α-酰氧基硫化物的高选择性、环境友好和可扩展的电化学方案。它具有极其广泛的底物范围、高区域选择性、克级合成、复杂分子的构建以及对各种亲核试剂的适用性。此外，软X射线吸收技术和一系列控制实验已被用来证明基板自组装的关键作用，这确实是我们电化学方案中高区域选择性的出色兼容性和精确控制的原因.
• Gold-Catalyzed, Iodine(III)-Mediated Direct Acyloxylation of the Unactivated C(sp³)-H Bonds of Methyl Sulfides
  作者：Sheng-rong Guo、Pailla Santhosh Kumar、Yan-qin Yuan、Ming-hua Yang

  DOI：10.1002/ejoc.201600632

  日期：2016.9

  An efficient reaction for the iodine(III)‐mediated acyloxylation of the unactivated C(sp3)–H bonds of methyl sulfides is reported. This strategy utilizes various hypervalent iodine reagents and involves an ionic pathway to deliver the desired products in excellent yields (DCE = 1,2‐dichloroethane).

  据报道，由碘（III）介导的未活化的甲基硫醚的C（sp 3）-H键可进行有效的酰氧基化反应。该策略利用了各种高价碘试剂，并涉及离子途径以极高的收率（DCE = 1,2-二氯乙烷）交付所需的产品。
• Direct α-acyloxylation of organic sulfides with the hypervalent (diacyloxyiodo)benzene/tetra-n-butylammonium bromide (TBAB) reagent combination
  作者：Dan Zhu、Denghu Chang、Shaoyan Gan、Lei Shi

  DOI：10.1039/c6ra01799a

  日期：——

  A novel metal-free approach to directly synthesize α-acyloxy sulfides from readily available alkyl sulfides utilizing the hypervalent (diacyloxyiodo)benzene and TBAB reagent combination is reported. This transformation is characterized by its broad substrate scope in moderate to excellent yields, convenient operating conditions and outstanding functional group tolerance.

  报道了一种新颖的无金属方法，该方法利用超价（二酰氧基碘）苯和TBAB试剂的组合，从容易获得的烷基硫化物中直接合成α-酰氧基硫化物。这种转变的特征在于其广泛的底物范围，具有中等至优异的产率，便利的操作条件和出色的官能团耐受性。
• Bredereck et al., Chemische Berichte, 1954, vol. 87, p. 784,787
  作者：Bredereck et al.

  DOI：——

  日期：——
• Enzyme-promoted kinetic resolution of acetoxymethyl aryl sulfoxides
  作者：Małgorzata Kwiatkowska、Ignacy Janicki、Piotr Kiełbasiński

  DOI：10.1016/j.molcatb.2015.04.016

  日期：2015.8

  A simple and efficient method of the synthesis of enantiomerically enriched, unknown acetoxymethyl aryl sulfoxides has been developed which is based on an enzyme-catalyzed hydrolysis of racemic substrates under the kinetic resolution conditions. The hydrolysis was performed not only in a buffer solution but also in diisopropyl ether in the absence of the external water added to give in some cases the products with ee up to 98%. The enantioselectivity of both procedures was dependent on the enzyme used and the aryl substituent, being lower for p-tolyl than for phenyl. A comparative asymmetric synthesis based on the oxidation of the corresponding sulfides using chiral oxidizing reagent turned out to be inferior to the method described. Absolute configuration of the newly synthesized compounds was ascribed on the basis of CD spectra. (C) 2015 Elsevier B.V. All rights reserved.