1-chloro-3-((4-methylphenyl)thio)propan-2-ol | 13708-10-6

• 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-chloro-3-((4-methylphenyl)thio)propan-2-ol
• 英文别名: 3-(4-methylphenylthio)-1-chloropropan-2-ol；1-chloro-3-(4-tolyl)thio-propane-2-ol；1-chloro-3-(p-tolylthio)propan-2-ol；1-Chlor-3-p-tolylmercapto-propanol-(2)；1-Chloro-3-(4-methylphenyl)sulfanylpropan-2-ol
• CAS: 13708-10-6
• 化学式: C₁₀H₁₃ClOS
• 分子量: 216.732
• InChiKey: ZQGKHCIZMHQINH-UHFFFAOYSA-N

物化性质

• 沸点：
  151-152 °C(Press: 1 Torr)
• 密度：
  1.20±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：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸异丙烯酯 、 1-chloro-3-((4-methylphenyl)thio)propan-2-ol 在 Chirazyme L-2 (c-f lyo) Candida antarctica lipase 作用下， 以 甲苯 为溶剂， 反应 168.0h， 生成 (S)-1-chloro-3-((4-methylphenyl)thio)propan-2-ol 、 (R)-1-chloro-3-((4-methylphenyl)thio)propan-2-ol 、 (R)-(-)-1-chloro-3-((4-methylphenyl)thio)propan-2-yl acetate 、 (S)-(-)-1-chloro-3-((4-methylphenyl)thio)propan-2-yl acetate
  参考文献：
  名称：

  Lipase-catalyzed separation of the enantiomers of 1-substituted-3-arylthio-2-propanols

  摘要：

  Optically active (R)- and (S)-1-substituted-3-(arylthio)propan-2-ols have been prepared in the reaction of the appropriate 2-(arylthiomethyl)oxiranes with chloride and azide anions followed by a lipase-catalyzed transesterification. The effects of the enzyme preparation as well as of the reaction conditions have been compared in terms of the enantiomeric excess of the obtained acetate and unreacted alcohol. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.040
• 作为产物：
  描述：

  p-tolylsulfanylmethyl-oxirane 在 potassium chloride 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 生成 1-chloro-3-((4-methylphenyl)thio)propan-2-ol
  参考文献：
  名称：

  Lipase-catalyzed separation of the enantiomers of 1-substituted-3-arylthio-2-propanols

  摘要：

  Optically active (R)- and (S)-1-substituted-3-(arylthio)propan-2-ols have been prepared in the reaction of the appropriate 2-(arylthiomethyl)oxiranes with chloride and azide anions followed by a lipase-catalyzed transesterification. The effects of the enzyme preparation as well as of the reaction conditions have been compared in terms of the enantiomeric excess of the obtained acetate and unreacted alcohol. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.040

文献信息

• Regioselective ring-opening reactions of 1,2-epoxides with thiols and arylselenols directly promoted by [Bmim]BF4
  作者：Ming-Hua Yang、Guo-Bing Yan、Yun-Fa Zheng

  DOI：10.1016/j.tetlet.2008.08.109

  日期：2008.11

  Regioselective ring-opening reactions of 1,2-epoxides with ArSH and ArSeH promoted by ionic liquid [Bmim]BF4 were investigated. A variety of β-hydroxy selenides and β-hydroxy sulfides were obtained in excellent yields (81–99%) with good regioselectivities using a mild, simple and environmentally benign procedure.

  研究了离子液体[Bmim] BF 4促进的1,2-环氧化物与ArSH和ArSeH的区域选择性开环反应。使用温和，简单且对环境有益的方法，可以以优异的收率（81–99％）获得各种β-羟基硒化物和β-羟基硫化物，且具有良好的区域选择性。
• Cyanuric Chloride: an Efficient Catalyst for Ring Opening of Epoxides with Thiols Under Solvent-Free Conditions
  作者：Babasaheb P. Bandgar、Neeta S. Joshi、Vinod T. Kamble、Sanjay S. Sawant

  DOI：10.1071/ch07079

  日期：——

  2,4,6-Trichloro-1,3,5-triazine-catalyzed convenient and efficient ring opening of epoxides with thiols under solvent-free conditions is described. Short reaction time, mild reaction conditions, inexpensive and readily available catalyst, and excellent yields of products are attractive features of this methodology.

  本研究描述了在无溶剂条件下，2,4,6-三氯-1,3,5-三嗪催化环氧化物与硫醇进行便捷高效的开环反应。反应时间短、反应条件温和、催化剂廉价易得、产物收率极高，这些都是该方法的诱人之处。
• Efficient Synthesis of <font>β</font>-Hydroxy Sulfides and <font>β</font>-Hydroxy Sulfoxides Catalyzed by Cu/MgO Under Solvent-Free Conditions
  作者：Biswanath Das、Penagaluri Balasubramanyam、Maddeboina Krishnaiah、Boyapati Veeranjaneyulu、Dega Sudhakar

  DOI：10.1080/00397910903219500

  日期：2010.6.25

  Regio-, stereo-, and chemoselective ring opening of epoxides with thiols using Cu/MgO as a heterogeneous catalyst has efficiently been carried out to produce the corresponding β-hydroxy sulfides in excellent yields at room temperature under solvent-free conditions. The treatment of the epoxides with thiols and 50% aqueous H2O2 in the presence of the same catalyst at room temperature affords the β-hydroxy

  使用 Cu/MgO 作为多相催化剂，环氧化物与硫醇的区域选择性、立体选择性和化学选择性开环已被有效地进行，以在室温和无溶剂条件下以优异的产率生产相应的 β-羟基硫化物。在室温下，在相同催化剂的存在下，用硫醇和 50% 的 H2O2 水溶液处理环氧化物以极好的收率提供了 β-羟基亚砜。
• An efficient catalyst for ring opening of epoxides with phenol and thiophenol under solvent-free conditions
  作者：Hong-fei Lu、Jun-tao Zhou、He-long Cheng、Lei-lei Sun、Fei-fei Yang、Run-ze Wu、Yu-hua Gao、Zhi-bin Luo

  DOI：10.1016/j.tet.2013.10.098

  日期：2013.12

  An efficient and rapid procedure for ring opening reaction of various epoxides with phenol and thiophenol derivatives was developed. The procedure can be obtained at room temperature under solvent-free condition in presence of (C4H12N2)(2)[Bicl(6)]Cl center dot H2O (1 mol %). This catalyst can be reused several times without significant loss of activity. (C) 2013 Elsevier Ltd. All rights reserved.
• Highly Regioselective Ring Opening of Epoxides with Thiols Catalyzed by SbCl₃Under Solvent-Free Conditions
  作者：Dadkhoda Ghazanfari、Mohammed M. Hashemi、Mohammad Reza Akhgar、Mohammad Mehdi Foroughi、Fariba Najafi-Zadeh

  DOI：10.1080/10426500802053201

  日期：2008.11.7

  The ring-opening reaction of epoxides with thiols by SbCl3 supported on Kieselguhr under solvent-free conditions, afforded high yields of -hydroxy sulfides. Nucleophilic attack of the thiols occurs regioselectively at the less hindered side of the epoxides.