1-isopropoxy-3-(phenylsulfanyl)propan-2-ol | 84137-75-7

• 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-isopropoxy-3-(phenylsulfanyl)propan-2-ol
• 英文别名: 1-(Phenylsulfanyl)-3-[(propan-2-yl)oxy]propan-2-ol；1-phenylsulfanyl-3-propan-2-yloxypropan-2-ol
• CAS: 84137-75-7
• 化学式: C₁₂H₁₈O₂S
• mdl: MFCD19596216
• 分子量: 226.34
• InChiKey: ACMGDXBHUYIAKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  异丙基缩水甘油醚 、 苯硫酚 在 lithium hydroxide 作用下， 反应 0.33h， 以97%的产率得到1-isopropoxy-3-(phenylsulfanyl)propan-2-ol
  参考文献：
  名称：

  在无溶剂条件下 LiOH 催化环氧化物的简单开环

  摘要：

  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。

  DOI：

  10.1080/10426500903127573

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。
• 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.
• Additive‐Free Thiolysis of Epoxides in Water: A Green and Efficient Regioselective Pathway to β‐Hydroxy Sulfides
  作者：Saeed M. Abaee、Mohammad M. Mojtahedi、Hassan Abbasi、Ensieh R. Fatemi

  DOI：10.1080/00397910701749963

  日期：2008.1

  Room-temperature ring opening of various epoxides with aromatic thiols was carried out in water in the absence of any Lewis acid or additive. High yields of beta-hydroxy sulfides with excellent regioselectivity were obtained under very environmentally friendly conditions.
• Solvent-Free Thiolysis of Epoxides under Lithium Perchlorate Catalysis
  作者：Mohammad M. Mojtahedi、Hassan Abassi、M. Saeed Abaee、Bahareh Mohebali

  DOI：10.1007/s00706-005-0458-9

  日期：2006.4

  Solvent-free ring opening of 1,2-epoxides with thiols using catalytic amounts of lithium perchlorate affords high yields of beta-hydroxy sulfides. Nucleophilic attack of the thiols occurs regio-selectively at the sterically less hindered side of the epoxides.