1-((4-chlorophenyl)thio)-3-phenoxypropan-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-((4-chlorophenyl)thio)-3-phenoxypropan-2-ol
• 英文别名: 1-(4-chlorophenylthio)-3-phenyloxypropan-2-ol；gwx-912；1-(4-Chlorophenyl)sulfanyl-3-phenoxypropan-2-ol
• 化学式: C₁₅H₁₅ClO₂S
• 分子量: 294.802
• InChiKey: KYKLYDHJOFVEOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  烯丙基苯基醚 、 4-氯苯硫酚 在 氧气 、 β-环糊精 作用下， 以 水 、 丙酮 为溶剂， 反应 6.0h， 以64%的产率得到1-((4-chlorophenyl)thio)-3-phenoxypropan-2-ol
  参考文献：
  名称：

  Synthesis of β-Hydroxysulfides from Alkenes under Supramolecular Catalysis in the Presence of β-Cyclodextrin in Water

  摘要：

  An environmentally benign and highly efficient procedure has been developed for the direct one-pot synthesis of beta-hydroxysulfides in good yields under neutral conditions from alkenes and thiophenols in the presence of aerial oxygen using beta-cyclodextrin in water. This protocol tolerates a wide variety of functional groups or substrates and does not require the use of either acid or base catalysts. beta-Cyclodextrin can be recovered and reused for a number of runs without any loss of activity.

  DOI：

  10.1021/jo060805a

文献信息

• Facile Room-Temperature MgBr₂· OEt₂-Catalyzed Thiolysis of Epoxides Under Solvent-Free Conditions
  作者：Mohammad M. Mojtahedi、M. Saeed Abaee、Mohammad Bolourtchian、Hassan Abbasi

  DOI：10.1080/10426500601088697

  日期：2007.2.15

  Solvent-free ring opening of 1,2-epoxides with aromatic and aliphatic thiols under 1 mol% magnesium bromide ethyl etherate catalysis affords rapid formation of β-hydroxy sulfides at ambient temperature with excellent yields. Nucleophilic attack of the thiols occurs regioselectively at the less hindered position of the epoxides.

  在 1 mol% 溴化镁乙基醚合物催化下，1,2-环氧化物与芳香族和脂肪族硫醇的无溶剂开环可在环境温度下以优异的产率快速形成 β-羟基硫化物。硫醇的亲核攻击区域选择性地发生在环氧化物的受阻较小的位置。
• LiOH-Catalyzed Simple Ring Opening of Epoxides Under Solvent-Free Conditions
  作者：Najmedin Azizi、Alireza Khajeh-Amiri、Hossein Ghafuri、Mohammad Bolourtchian

  DOI：10.1080/10426500903127573

  日期：2010.6.30

  sulfides and β-hydroxyl nitriles by ring opening of epoxides with aromatic, aliphatic, and heterocyclic thiols and trimethylsilyl cyanide at room temperature under solvent free conditions. All the reactions proceeded satisfactorily in short times and afforded the corresponding products in good to excellent yields with high regioselectivity and chemoselectivity under mild reaction conditions.

  已发现 LiOH 是一种非常简单且选择性的催化剂，可通过环氧化物与芳香族、脂肪族和杂环硫醇以及三甲基氰基氰化物在室温下在无溶剂条件下开环快速温和地合成 β-羟基硫化物和 β-羟基腈使适应。所有反应都在短时间内令人满意地进行，并在温和的反应条件下以良好的收率和高区域选择性和化学选择性提供相应的产物。
• Tandem base-free synthesis of β-hydroxy sulphides under ultrasound irradiation
  作者：GUANG-SHU LV、FU-JUN DUAN、JIN-CHANG DING、TIAN-XING CHENG、WEN-XIA GAO、JIU-XI CHEN、HUA-YUE WU

  DOI：10.1007/s12039-012-0305-6

  日期：2012.9

  Rongalite® promotes cleavage of diaryl disulphides generating the corresponding thiolate species in situ which then undergo facile ring-opening of epoxides in a regioselective manner under ultrasound irradiation, affording β-hydroxy sulphides in good to excellent yields. The important features of this methodology are base-free, odourless, high yield, reasonably rapid reaction rate, simple workup, high regioselectivity, cost-effective and no requirement of transition metal catalysts. It is noteworthy that ring-opening reaction of 1,2-diphenyldiselane with 2-(phenoxymethyl)oxirane are also conducted smoothly to afford β-hydroxy selenide in excellent yield under the standard conditions.

  Rongalite® 可促进二芳基二硫化物的裂解，在原位生成相应的硫代硫酸盐，然后在超声波辐照下以区域选择性的方式对环氧化物进行简便的开环反应，从而以良好到极佳的收率生成 β-羟基硫化物。这种方法的重要特点是无碱、无味、产率高、反应速度快、操作简单、高区域选择性、成本效益高，而且不需要过渡金属催化剂。值得注意的是，在标准条件下，1,2-二苯基二硒烷与 2-（苯氧基甲基）环氧乙烷的开环反应也能顺利进行，并以极好的收率得到 β-羟基硒化物。
• Recyclable superparamagnetic Fe3O4 nanoparticles for efficient catalysis of thiolysis of epoxides
  作者：Mohammad M. Mojtahedi、M. Saeed Abaee、Azam Rajabi、Peyman Mahmoodi、Saeed Bagherpoor

  DOI：10.1016/j.molcata.2012.05.004

  日期：2012.9

  An efficient and rapid procedure is developed for room-temperature ring opening of various epoxides with thiols under solvent-free conditions in the presence of catalytic amount of superparamagnetic Fe3O4 nanoparticles. As a result, high conversion of reactants to various beta-hydroxy sulfides is observed in short time periods while the heterogeneous catalyst could be recovered and reused over several cycles without loosing its activity. Competitive reactions show higher reactivity of aromatic thiols over the aliphatic counterparts. (c) 2012 Elsevier B.V. All rights reserved.
• Stereo‐ and Regioselective Thiolysis of 1,2‐Epoxides in Water
  作者：Barahman Movassagh、Mohammad Soleiman‐Beigi

  DOI：10.1080/00397910701548100

  日期：2007.9.1