2-(2-aminophenylthio)-1-phenylethanol | 100710-54-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(2-aminophenylthio)-1-phenylethanol
• 英文别名: 2-(o-Aminophenylthio)-1-phenylethanol；gwx-919；2-(2-amino-phenylsulfanyl)-1-phenyl-ethanol；2-(2-Amino-phenylmercapto)-1-phenyl-aethanol；2-[(2-Aminophenyl)sulfanyl]-1-phenylethan-1-ol；2-(2-aminophenyl)sulfanyl-1-phenylethanol
• CAS: 100710-54-1
• 化学式: C₁₄H₁₅NOS
• mdl: MFCD13161533
• 分子量: 245.345
• InChiKey: CKIUIBQGVLWRPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 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：
  71.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-硝基苯硫氯 在 palladium on activated charcoal sodium tetrahydroborate 作用下， 生成 2-(2-aminophenylthio)-1-phenylethanol
  参考文献：
  名称：

  Organic sulfur compounds. VI. Reduction of three α-(o-nitrophenylthio)ketones with sodium borohydride

  摘要：

  用氢化钠和钯-活性炭还原三个α-(o-硝基苯硫基)酮，主要生成α-(o-硝基苯硫基)醇，次要产物为α-(o-氨基苯硫基)醇。只形成了两个苯并噻嗪。对-(o-硝基苯硫基)苯乙酮的催化还原产物中，双[2-(3-苯基-2H-1,4-苯并噻嗪)]是一个次要产物，而1-(3,4-二氢-4-羟基-3-酮-2H-1,4-苯并噻嗪-2-基)苄醇是α-苯甲酰-α-(o-硝基苯硫基)醋酸酯的催化还原的主要产物。

  DOI：

  10.1139/v70-414

文献信息

• 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。
• Polystyrene-Supported 1,5,7-Triazabicyclo[4.4.0]dec-5-ene as an Efficient and Reusable Catalyst for the Thiolysis of 1,2-Epoxides under Solvent-Free Conditions
  作者：Francesco Fringuelli、Ferdinando Pizzo、Carla Vittoriani、Luigi Vaccaro

  DOI：10.1002/ejoc.200500791

  日期：2006.3

  Polystyrene-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (PS-TBD) is an effective basic catalyst for the thiolysis of the 1,2-epoxides 1a–e by the aryl- and alkyl-substituted thiols 2A–E under solvent-free conditions while its activity is remarkably reduced in MeCN. The reactions are totally anti-diastereoselective and generally highly C-β regioselective. The corresponding hydroxy sulfides have been

  聚苯乙烯负载的 1,5,7-三氮杂双环 [4.4.0]dec-5-烯 (PS-TBD) 是一种有效的碱性催化剂，用于通过芳基-和烷基-硫解 1,2-环氧化物 1a-e在无溶剂条件下取代硫醇 2A-E，而其活性在 MeCN 中显着降低。这些反应是完全抗非对映选择性的，并且通常具有高度的 C-β 区域选择性。相应的羟基硫化物已以优异的产率分离出来，并且催化剂很容易回收和再利用，而不会降低工艺的效率和选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Verfahren zur Herstellung von 2,3-Dihydro-4H-1,4-benzothiazinen
  申请人：BAYER AG

  公开号：EP0061082A1

  公开（公告）日：1982-09-29

  Verfahren zur Herstellung von 2,3-Dihydro-4H-1,4-benzothiazinen durch Cyclisierung entsprechender 2-(2-Hydroxyalkyl)-thioaniline unter Wasserabspaltung in Gegenwart von phosphoriger Säure.

  在磷酸存在下，通过相应的 2-(2-羟基烷基)-硫代苯胺环化脱水制备 2,3-二氢-4H-1,4-苯并噻嗪的工艺。
• 66. Reactions of ethylene oxides. Part II. Reactions with thioamides, thiols, and inorganic sulphur salts
  作者：C. C. J. Culvenor、W. Davies、N. S. Heath

  DOI：10.1039/jr9490000278

  日期：——
• 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.