1-(4-巯基苯基)乙醇 | 77069-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 中文名称: 1-(4-巯基苯基)乙醇
• 英文名称: 1-(4-mercaptophenyl)ethanol
• 英文别名: 1-(4-Mercapto-phenyl)-aethanol；4'-(1-hydroxyethyl) thiophenol；1-(4-Sulfanylphenyl)ethan-1-ol；1-(4-sulfanylphenyl)ethanol
• CAS: 77069-55-7
• 化学式: C₈H₁₀OS
• mdl: MFCD19301042
• 分子量: 154.233
• InChiKey: OEFNBHQZFVQRJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-巯基苯基)乙醇 以97%的产率得到
  参考文献：
  名称：

  ASLAM, MOHAMMAD;DAVENPORT, KENNETH G.

  摘要：

  DOI：
• 作为产物：
  描述：

  4'-巯基苯乙酮 在 吡啶 、 sodium tetrahydroborate 、 乙醚 、 乙醇 作用下， 生成 1-(4-巯基苯基)乙醇
  参考文献：
  名称：

  Preparation of p-Vinylphenyl Thioacetate,¹ its Polymers, Copolymers and Hydrolysis Products. Water-soluble Copolymers Containing Sulfhydryl Groups²

  摘要：

  DOI：

  10.1021/ja01599a067

文献信息

• Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
  作者：Yajun Liu、Jihye Kim、Heesun Seo、Sunghyouk Park、Junghyun Chae

  DOI：10.1002/adsc.201400941

  日期：2015.7.6

  single‐step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2‐ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high

  利用铜（II）催化剂和1,2-乙二硫醇开发了一种高效的过渡金属催化的从芳基卤化物单步合成芳基硫醇的方法。关键特征是使用现成的试剂，简单的操作以及相对温和的反应条件。该新协议显示了广泛的底物范围，具有出色的官能团相容性。由芳基卤化物直接以高收率制备各种芳基硫醇。此外，芳基硫醇原位用于合成更高级的分子，例如二芳基硫醚和苯并噻吩。
• A General and Efficient Approach to Aryl Thiols: CuI-Catalyzed Coupling of Aryl Iodides with Sulfur and Subsequent Reduction
  作者：Yongwen Jiang、Yuxia Qin、Siwei Xie、Xiaojing Zhang、Jinhua Dong、Dawei Ma

  DOI：10.1021/ol902186d

  日期：2009.11.19

  A CuI-catalyzed coupling reaction of aryl iodides and sulfur powder takes place in the presence of K2CO3 at 90 °C. The coupling mixture is directly treated with NaBH4 or triphenylphosphine to afford aryl thiols in good to excellent yields. A wide range of substituted aryl thiols that bear methoxy, hydroxyl, carboxylate, amido, keto, bromo, and fluoro groups can be assembled through this procedure.

  CuI催化的芳基碘化物和硫粉的偶联反应在90°C的K 2 CO 3存在下进行。偶联混合物直接用NaBH 4或三苯基膦处理，以良好或优异的收率得到芳基硫醇。可以通过该程序组装具有甲氧基，羟基，羧酸酯基，酰胺基，酮基，溴基和氟基的各种各样的取代的芳基硫醇。
• [EN] GAMMA SECRETASE MODULATORS<br/>[FR] MODULATEURS DE GAMMA SECRÉTASE
  申请人：SCHERING CORP

  公开号：WO2009045314A1

  公开（公告）日：2009-04-09

  In its many embodiments, the present invention provides a novel class of 5-membered, nitrogen-containing heterocyclic compounds as modulators of gamma secretase, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the central nervous system using such compounds or pharmaceutical compositions.

  在其许多实施例中，本发明提供了一种新型的含氮杂环5-成员化合物，作为γ-分泌酶的调节剂，制备这种化合物的方法，含有一种或多种这种化合物的药物组合物，制备包含一种或多种这种化合物的药物配方的方法，以及使用这种化合物或药物组合物治疗、预防、抑制或改善与中枢神经系统相关的一种或多种疾病的方法。
• [EN] GAMMA SECRETASE MODULATORS<br/>[FR] MODULATEURS DE SÉCRÉTASE GAMMA
  申请人：SCHERING CORP

  公开号：WO2010054067A1

  公开（公告）日：2010-05-14

  In its many embodiments, the present invention provides a novel class of heterocyclic compounds of the formula: as modulators of gamma secretase, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the central nervous system using such compounds or pharmaceutical compositions.

  在其许多实施例中，本发明提供了一类新型的杂环化合物，其化学式为：作为γ-分泌酶调节剂，制备这类化合物的方法，含有一种或多种这类化合物的药物组合物，制备含有一种或多种这类化合物的制剂的方法，以及使用这类化合物或药物组合物治疗、预防、抑制或改善与中枢神经系统相关的一种或多种疾病的方法。
• Method for producing alkenylthiophenols and their esters
  申请人：Hoechst Celanese Corporation

  公开号：US04794205A1

  公开（公告）日：1988-12-27

  A method is provided for preparing alkenylthiophenols, e.g., para-vinylthiophenol, or their esters, e.g., para-vinylthiophenol acetate by reacting a hydroxy aromatic ketone, e.g., 4-hydroxyacetophenone (4-HAP) with an N,N-di(organo)thiocarbamoyl halide, e.g., N,N-dimethylthiocarbamoyl chloride (DMTC) to form an O-(acylaryl) N,N-di(organo)thiocarbamate, e.g., O-(4'-acetophenyl) N,N-dimethylthiocarbamate, and pyrolytically rearranging the latter compound to form an S-(acylaryl) N,N-di(organo)thiocarbamate, e.g., S-(4-4- -acetophenyl) N,N-dimethylthiocarbamate. In one procedure, the latter compound is directly reduced to form an S-(1-hydroxyalkylaryl) N,N-di(organo) thiocarbamate, e.g., S-[4'-(1-hydroxyethyl)phenyl] N,N-dimethylthiocarbamate, which is either hydrolyzed to form a (1-hydroxyalkyl) thiophenol, e.g., 4'-(1-hydroxyethyl) thiophenol, which optionally after acylation of its thiol group, is dehydrated to form the alkenylthiophenol wherein the double bond is at the ring-bonded carbon atom, e.g., para-vinylthiophenol, or the S-(1-hydroxyalkylaryl) N,N-di(organo) thiocarbamate is dehydrated to form an S-(alkenylaryl) N,N-di(organo) thiocarbamate, e.g., S-(4-vinylphenyl) N,N-dimethylthiocarbamate which is hydrolyzed to form the alkenylthiophenol. In an alternative procedure, the S-(acylaryl) N,N-di(organo)thiocarbamate is hydrolyzed and the resulting thiol acylated with an acylating agent, e.g., acetyl chloride, to produce an acylthiophenol ester, e.g., 4-acetothiophenol acetate, which is then reduced and hydrolyzed to produce the (1-hydroxyalkyl) thiophenol. The latter compound is then dehydrated to produce the alkenylthiophenol, or acylated and dehydrated to produce alkenylthiophenol thioester, as described in the first procedure.

  提供了一种制备烯基硫代苯酚，例如对-乙烯基硫代苯酚，或其酯，例如对-乙烯基硫代苯酚醋酸酯的方法，通过将羟基芳香酮，例如4-羟基乙酰苯酮（4-HAP）与N,N-二（有机）硫代氨酰卤化物，例如N,N-二甲基硫代氨酰氯（DMTC）反应形成O-（酰基芳基）N,N-二（有机）硫代氨酰酸盐，例如O-（4'-乙酰苯基）N,N-二甲基硫代氨酰酸盐，并通过热解重排后者化合物形成S-（酰基芳基）N,N-二（有机）硫代氨酰酸盐，例如S-（4-4- -乙酰苯基）N,N-二甲基硫代氨酰酸盐。在一个程序中，后者化合物直接还原形成S-（1-羟基烷基芳基）N,N-二（有机）硫代氨酰酸盐，例如S-[4'-(1-羟基乙基)苯基]N,N-二甲基硫代氨酰酸盐，它可以水解形成（1-羟基烷基）硫代苯酚，例如4'-(1-羟基乙基)硫代苯酚，之后经过硫醇基的酰化，脱水形成烯基硫代苯酚，其中双键位于环键合碳原子，例如对-乙烯基硫代苯酚，或将S-（1-羟基烷基芳基）N,N-二（有机）硫代氨酰酸盐脱水形成S-（烯基芳基）N,N-二（有机）硫代氨酰酸盐，例如S-（4-乙烯基苯基）N,N-二甲基硫代氨酰酸盐，将其水解形成烯基硫代苯酚。在另一种程序中，S-（酰基芳基）N,N-二（有机）硫代氨酰酸盐被水解，生成的巯基与酰化剂，例如乙酰氯，酰化，产生酰硫代苯酚酯，例如4-乙酰硫代苯酚醋酸酯，然后还原和水解产生（1-羟基烷基）硫代苯酚。后者化合物然后脱水产生烯基硫代苯酚，或酰化和脱水产生烯基硫代苯酚硫酯，如第一程序中所述。