2-phenyl-1-(p-tolylthio)propan-2-ol | 681006-46-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-phenyl-1-(p-tolylthio)propan-2-ol
• 英文别名: 1-(4-Methylphenyl)sulfanyl-2-phenylpropan-2-ol
• CAS: 681006-46-2
• 化学式: C₁₆H₁₈OS
• 分子量: 258.384
• InChiKey: WZUAYWMXJGKRFU-UHFFFAOYSA-N

物化性质

• 沸点：
  405.3±40.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-甲基苯基亚硫酰氯 在 三氯氧磷 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 2-phenyl-1-(p-tolylthio)propan-2-ol
  参考文献：
  名称：

  p-Tolylsulfinyl Amides:  Reagents for Facile Electrophilic Functionalization of Olefins

  摘要：

  A variety of olefins were found to react with sulfinyl amides in the presence of POCl3 to give beta-chlorosulfides and beta-hydroxysulfides in good yields. In the absence of nucleophiles, p-tolylsulfinyl amides were found to react with olefins with the formation of allylsulfoxides.

  DOI：

  10.1021/jo035518a

文献信息

• Auto-oxidative hydroxysulfenylation of alkenes
  作者：Congde Huo、Yajun Wang、Yong Yuan、Fengjuan Chen、Jing Tang

  DOI：10.1039/c6cc01937d

  日期：——

  One-pot auto-oxidation mediated hydroxysulfenylation of electron-deficient and electron-rich olefins with phenthiols was explored.

  一锅法介导的电子不足和电子富集烯烃与苯硫醇的羟基硫醚化反应被探索。
• Copper(II) Acetate-Catalyzed Hydroxysulfenylation-Initiated Lactonization of Unsaturated Carboxylic Acids with Oxygen as Oxidant and Oxygenation Reagent
  作者：Bingnan Du、Yang Wang、Haibo Mei、Jianlin Han、Yi Pan

  DOI：10.1002/adsc.201700036

  日期：2017.5.17

  thiols has been explored. The reaction proceeds through a new hydroxysulfenylation-initiated lactonization pathway with carboxyl as electrophilic group, which provides an efficient access to assembly highly valuable thio-substituted lactone derivatives with good yields under mild conditions. Several control experiments, as well as an isotope labelling experiment disclose that oxygen acts as both oxidant

  已经研究了乙酸铜（II）催化的C = C双键的需氧硫醇化，氧合以及不饱和羧酸与硫醇的分子内环化反应。该反应通过以羧基为亲电基团的新的羟基磺酰化引发的内酯化途径进行，这提供了在温和条件下以良好收率高效组装高价硫取代的内酯衍生物的途径。几个对照实验以及同位素标记实验表明，氧气既是氧化剂，又是反应物，被转移到最终产物中。机理研究支持通过基于不饱和羧酸的烯烃的双官能化来构建新取代内酯的新策略的发现。
• Hydroxysulfenylation of Electron-Deficient Alkenes through an Aerobic Copper Catalysis
  作者：Hui Xi、Bicheng Deng、Zhenzhen Zong、Shenglin Lu、Zhiping Li

  DOI：10.1021/acs.orglett.5b00112

  日期：2015.3.6

  A copper-catalyzed hydroxysulfenylation of α,β-unsaturated esters/amides is reported. The method presents a selective and efficient synthesis of β-hydroxysulfides bearing electron-withdrawing groups. The synthetic utility of this method is demonstrated by the concise synthesis of the anticancer drug bicalutamide.

  据报道，铜催化的α，β-不饱和酯/酰胺的羟基亚磺酰基化。该方法提出了具有吸电子基团的β-羟基硫化物的选择性和有效的合成。该方法的合成效用通过抗癌药物比卡鲁胺的简明合成得到证明。
• Aerobic Copper(II)-catalyzed synthesis of β-hydroxysulfides and selenides from alkenes with disulfides and diselenides
  作者：Nobukazu Taniguchi

  DOI：10.1016/j.tet.2022.132689

  日期：2022.3

  A copper-catalyzed hydroxysulfenylation of alkenes was achieved using disulfides in the presence of n-Bu4NI and H2O. The procedure smoothly proceeded under air atmosphere, and the corresponding β-hydroxysulfides were obtained with regio- and anti-selectivity in good yields. Furthermore, a reaction using diselenides effectively produced the expected β-hydroxyselenides. These reactions could use both

  在 n-Bu 4 NI 和 H 2 O存在下，铜催化烯烃的羟基亚磺酰化反应，在n- Bu 4 NI 和 H 2 O 存在下，反应过程顺利进行，得到了区域选择性和抗选择性良好的β-羟基硫化物。产量。此外，使用二硒化物的反应有效地产生了预期的β-羟基硒化物。这些反应可以使用二硫属化物上的两个硫属化物基团。此外，该程序还适用于使用硫醇进行的氢化亚磺酰化。
• Formate‐Mediated Synthesis of β‐Hydroxysulfides from Olefins and Thiosulfonates via EDA Complex Strategy under Visible Light Irradiation in Air
  作者：Qing Shen、Xiaoyan Peng、Jiahong Sui、Min Peng、Xiangwei Liu、Hezhong Jiang、Rui Tan、Min Zhou、Jiahong Li

  DOI：10.1002/cjoc.202400530

  日期：2024.12

  A visible-light-induced and efficient one-pot synthesis of β-hydroxysulfides from olefins, thiosulfonates and HCOOCs using an EDA complex strategy under air atmosphere at room temperature has been disclosed. A plausible radical involved mechanism is proposed. During the reaction process, formates play a crucial role: first, as donors in the EDA complex; second, as providers of the hydrogen source;

  在室温下空气气氛下，使用 EDA 复合物策略从烯烃、硫代磺酸盐和 HCOOCs 中以可见光诱导的高效一锅法合成 β-羟基硫化物已被披露。提出了一种合理的根式参与机制。在反应过程中，甲酸盐起着至关重要的作用：首先，作为 EDA 复合物中的供体;第二，作为氢源的提供者;第三，通过产生 CO2•– 来减少过氧化物中间体，从而形成 β-羟基硫化物。与之前报道的巯基-氧共氧化反应相比，这种简单且可持续的方法具有反应条件温和、操作简单、无味和出色的官能团耐受性。