1-(4-chlorophenyl)-2-((4-chlorophenyl)thio)ethan-1-ol | 1174708-86-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(4-chlorophenyl)-2-((4-chlorophenyl)thio)ethan-1-ol
• 英文别名: 1-(4-chlorophenyl)-2-(4-chlorophenylthio)ethanol；1-(4-Chlorophenyl)-2-(4-chlorophenyl)sulfanylethanol
• CAS: 1174708-86-1
• 化学式: C₁₄H₁₂Cl₂OS
• mdl: MFCD23146639
• 分子量: 299.221
• InChiKey: TZJREKMJBKNOBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯乙烯 、 4-氯苯硫酚 在 碘 、 二甲基亚砜 作用下， 反应 12.0h， 以75%的产率得到1-(4-chlorophenyl)-2-((4-chlorophenyl)thio)ethan-1-ol
  参考文献：
  名称：

  碘催化的β-羟基硫化物的区域选择性合成

  摘要：

  已经开发了一种无金属且环境友好的碘催化方案，用于以易于获得的苯乙烯和苯酚为原料，以良好至极好的收率，选择性地合成β-羟基硫化物。该反应涉及单步C S和C O键的构建。

  DOI：

  10.1016/j.tetlet.2017.04.043

文献信息

• Aerobic oxysulfonylation of alkenes using thiophenols: an efficient one-pot route to β-ketosulfones
  作者：Atul K. Singh、Ruchi Chawla、Twinkle Keshari、Vinod K. Yadav、Lal Dhar S. Yadav

  DOI：10.1039/c4ob00776j

  日期：——

  We have developed a highly efficient synthetic route to β-ketosulfones via AgNO3 catalyzed oxysulfonylation of alkenes using thiophenols in the presence of air (O2) and K2S2O8 as eco-friendly oxidants. Thiophenols have been used as sulfonylation precursors for the first time in a dioxygen activation based radical process. Moreover, the protocol also offers a new and convenient method for the synthesis

  我们已经开发出了一种高效的合成路线，该路线是在空气（O 2）和K 2 S 2 O 8作为生态友好型氧化剂的情况下，通过使用苯硫酚通过AgNO 3催化的烯烃的氧磺酰化反应。硫酚在基于双氧活化的自由基工艺中首次被用作磺酰化前体。此外，该方案还提供了一种在不使用任何引发剂的情况下，在室温下合成β-羟基硫化物的新型便捷方法。
• HBr/H 2 O 2 -mediated formation of C–S bond with thiosulfates
  作者：Rongxing Zhang、Shengzhou Jin、Yuanxing Wan、Sen Lin、Zhaohua Yan

  DOI：10.1016/j.tetlet.2018.01.055

  日期：2018.2

  environmentally-friendly H2O2 as oxidant and HBr as catalyst. Based on the preliminary experimental results, a plausible reaction mechanism was proposed for HBr/H2O2-mediated formation of C–S bond with thiosulfates.

  通过HBr / H 2 O 2介导的苯乙烯和4-羟基香豆素的亚磺酰基化反应导致不对称硫化物的形成，一种新颖，有效且绿色的构建C–S键的方案得以开发。使用环境友好的H 2 O 2作为氧化剂和HBr作为催化剂，一步一步制备各种不对称硫化物，并具有中等至良好的收率。根据初步的实验结果，提出了一种可能的反应机理，该反应机理是HBr / H 2 O 2介导的与硫代硫酸盐形成CS键的反应。
• Molecular Iodine Catalyzed Hydroxysulfenylation of Alkenes with Disulfides in Aerobic Conditions
  作者：Bang-qing Ni、Yunpeng He、Xuejiao Rong、Teng-fei Niu

  DOI：10.1055/s-0039-1690163

  日期：2019.9

  molecular-iodine-catalyzed radical reaction. This reaction involves hydroxysulfenylation of alkenes with disulfides in aqueous solution. Air is used as the oxidant without any additives. Control experiments indicated that the oxygen atom of products might come from O2. Both aryl alkenes and aliphatic alkenes were well tolerated in this transformation and afforded the corresponding products in moderate

  通过分子碘催化自由基反应制备β-羟基硫化物的环境友好且高效的策略已被开发出来。该反应涉及烯烃与二硫化物在水溶液中的羟基亚磺酰化。空气用作氧化剂，不加任何添加剂。对照实验表明产物的氧原子可能来自O2。芳基烯烃和脂肪族烯烃在该转化中均具有良好的耐受性，并以中等至高产率提供相应的产物。
• Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System
  作者：Jiawei Huang、Xiaoman Li、Liang Xu、Yu Wei

  DOI：10.1021/acs.joc.2c02856

  日期：2023.3.3

  A three-component oxychalcogenation reaction, from alkenes, diselenides/thiophenols, and H2O/alcohols, has been realized herein. Tetrabutylammonium tribromide (TBATB) and dimethylsulfoxide (DMSO) are utilized as the catalyst and the terminal oxidant, respectively, to enable this difunctionalization transformation. The metal-free reaction system shows good functional group compatibility, providing a

  本文实现了烯烃、二硒化物/苯硫酚和 H 2 O/醇的三组分氧硫属化反应。四丁基三溴化铵 (TBATB) 和二甲基亚砜 (DMSO) 分别用作催化剂和末端氧化剂，以实现这种双官能化转化。无金属反应体系显示出良好的官能团相容性，为获得β-羟基或β-烷氧基有机硫族化合物提供了统一实用的途径。
• Rongalite® promoted highly regioselective synthesis of β-hydroxy sulfides by ring opening of epoxides with disulfides
  作者：Wenxue Guo、Jiuxi Chen、Dengze Wu、Jinchang Ding、Fan Chen、Huayue Wu

  DOI：10.1016/j.tet.2009.04.085

  日期：2009.7

  Rongaliteo (R) promotes cleavage of disulfides generating thiolate anions that then undergo facile ring opening of epoxides in the presence of K2CO3 to afford alpha-addition products 3 with good to excellent yields. The important features of this methodology are broad substrates scope, high yielding, reasonably rapid reaction rate, high regioselectivity and no requirement of metal catalysts. It should be noted that the thiolate anion attacks the epoxides derived from styrene to produce the corresponding alpha-addition products 3 with high regioselectivity, instead of the beta-addition regioisomer 4 that Could be formed from the attack of the nucleophile at the benzylic position. (C) 2009 Elsevier Ltd. All rights reserved.