2-(benzhydrylthio)ethan-1-ol | 94001-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(benzhydrylthio)ethan-1-ol
• 英文别名: 2-benzhydrylsulfanyl ethanol；2-benzhydrylsulfanyl-ethanol；2-benzhydrylmercapto-ethanol；2-Benzhydrylmercapto-aethanol；2-[(diphenylmethyl)thio]ethanol；2-Diphenylmethylmercapto-aethanol；2-benzhydrylsulfanylethanol
• CAS: 94001-59-9
• 化学式: C₁₅H₁₆OS
• 分子量: 244.357
• InChiKey: YBUBKZYKDXHLFJ-UHFFFAOYSA-N

物化性质

• 熔点：
  36-38 °C
• 沸点：
  184-185 °C(Press: 1 Torr)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2-(benzhydrylthio)ethan-1-ol 在 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 异丙醇 、 乙腈 为溶剂， 生成 1-(4-(2-(benzhydrylthio)ethyl)piperazin-1-yl)-3-phenylpropan-2-ol
  参考文献：
  名称：

  [EN] POTENT AND SELECTIVE INHIBITORS OF MONOAMINE TRANSPORTERS; METHOD OF MAKING; AND USE THEREOF
  [FR] INHIBITEURS PUISSANTS ET SÉLECTIFS DE TRANSPORTEURS DE MONOAMINE; PROCÉDÉ DE FABRICATION; ET LEUR UTILISATION

  摘要：

  公开号：

  WO2014138518A3
• 作为产物：
  描述：

  二苯甲醇 在 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 2-(benzhydrylthio)ethan-1-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of (R)-N-(diarylmethylthio/sulfinyl)ethyl/propyl-piperidine-3-carboxylic acid hydrochlorides as novel GABA uptake inhibitors

  摘要：

  A series of new (R)-1-(2-diarylmethylthio/sulfinyl) ethyl-pipei-idine-3-carboxylic acid hydrochlorides 5a-d/6a-d and (R)-1(3-diarylmethylthio) propyl-piperidine-3-carboxylic acid hydrochlorides 5'a-d were synthesized and evaluated as gamma-aminobutyric acid uptake inhibitors through cultured cell lines expressing mouse GAT1. Biological screening results demonstrated that the compounds 6a-d with diarylmethylsulfinyl ethyl side chain show more potent GAT-1 inhibitory activities than 5a-d/5'a-d with diary]methylthio ethyl/propyl moieties. Some of them, such as 6a, exhibited excellent inhibitions of [3 H]-GABA uptake in cultured cells, which is 496-fold higher than (R)-nipecotic acid and 11.5 times less than tiagabine. The synthesis and structure-activity relationships are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.010

文献信息

• Various N-substituted 3-piperidine carboxylic acids or N-substituted
  申请人：Warner-Lambert Company

  公开号：US04772615A1

  公开（公告）日：1988-09-20

  Analogs of nipecotic acid are the novel compounds of the present invention. The analogs are GABA uptake inhibitors for use to treat epilepsy and, thus, the invention is also pharmaceutical compositions and methods of use therefor.

  尼佩酸的类似物是本发明的新化合物。这些类似物是GABA摄取抑制剂，用于治疗癫痫，因此，该发明还涉及药物组合物和使用方法。
• Metal-Free Chemoselective Oxidation of Sulfides to Sulfoxides by Hydrogen Peroxide Catalyzed byin situ Generated Dodecyl Hydrogen Sulfate in the Absence of Organic Co-Solvents
  作者：H. Firouzabadi、N. Iranpoor、A. A. Jafari、E. Riazymontazer

  DOI：10.1002/adsc.200505312

  日期：2006.3

  The mild oxidation of sulfides to sulfoxides with an aqueous solution of H2O2 (35%) catalyzed by in situ generated dodecyl hydrogen sulfate as Brønsted acid surfactant in the absence of any organic co-solvents and under metal-free conditions is described. The method shows high chemoselectivity and the process is highly green for solid sulfoxides which crystallize out immediately after their formation

  描述了在不存在任何有机助溶剂且无金属的条件下，通过原位生成的十二烷基硫酸氢作为布朗斯台德酸表面活性剂催化的H 2 O 2（35％）水溶液将硫化物轻度氧化为亚砜的方法。该方法显示出高的化学选择性，固体亚砜在从反应混合物中形成后立即结晶出来，因此该过程是高度绿色的。液态亚砜可以在高真空下通过球到球蒸馏或通过用Et 2 O或EtOAc萃取来分离。产品的产率极好。
• Protic ionic liquids as recyclable solvents for the acid catalysed synthesis of diphenylmethyl thioethers
  作者：Luke C. Henderson、Megan T. Thornton、Nolene Byrne、Bronwyn L. Fox、Kelsey D. Waugh、Jennifer S. Squire、Linden Servinis、Joshua P. Delaney、Hannah L. Brozinski、Luke M. Andrighetto、Jarrad M. Altimari

  DOI：10.1016/j.crci.2013.04.002

  日期：2013.7

  Résumé The acid catalysed formation of diphenylmethyl (DPM) thioethers was successfully achieved using the protic ionic liquid (pIL) triethylamine:methanesulfonic acid (TeaMs) as the reaction solvent under microwave irradiation. A slight excess of methanesulfonic acid (10% v/v) was required to facilitate the reaction, which was applied to a variety of thiols. Aliphatic, aromatic and heterocyclic aromatic thiols were converted to their corresponding DPM thioethers in high yields (63–99%), in short reaction times (5–20 min) and using mild temperatures (80–100 °C). Finally, the pIL (TeaMS) was recycled five times without loss of yield.

  摘要 在微波辐照下，以三乙胺：甲基磺酸（TeaMs）原生离子液体（pIL）为反应溶剂，成功地实现了酸催化生成二苯基甲基（DPM）硫醚。为促进反应的进行，需要略微过量的甲磺酸（10% v/v），该反应适用于多种硫醇。脂肪族、芳香族和杂环芳香族硫醇在较短的反应时间（5-20 分钟）和温和的温度（80-100 °C）下被转化为相应的 DPM 硫醚，产率高（63-99%）。最后，pIL（TeaMS）被循环使用了五次，产率未受损失。
• POTENT AND SELECTIVE INHIBITORS OF MONOAMINE TRANSPORTERS; METHOD OF MAKING; AND USE THEREOF
  申请人：THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY DEPARTMENT OF HEALTH AND HUMAN SERVICE

  公开号：US20160009644A1

  公开（公告）日：2016-01-14

  Disclosed herein are bisarylmethylthioacetamides and bisarylmethylthioethylamines useful as inhibitors of monoamine transporters. The compounds are potent and/or selective inhibitors of dopamine (DA), serotonin (5-HT), and/or norepinephrine (NE) reuptake via their respective transporters, DAT, SERT and NET. Also disclosed are methods for eliciting a wake-promoting or cognitive or attention enhancing effect and for treating substance use disorders, attention deficit (hyperactivity) disorder, depressive disorders, bipolar disorder or other neuropsychiatric disorders sleep disorders or cognitive impairment using the compounds.

  本文揭示了双芳基甲硫基乙酰胺和双芳基甲硫基乙胺作为单胺转运体抑制剂的用途。这些化合物是通过它们各自的转运体DAT、SERT和NET对多巴胺（DA）、5-羟色胺（5-HT）和/或去甲肾上腺素（NE）的再摄取具有强效和/或选择性抑制作用。还揭示了利用这些化合物引发促醒、认知或注意力增强效应以及治疗物质使用障碍、注意缺陷（多动）障碍、抑郁障碍、双相障碍或其他神经精神障碍、睡眠障碍或认知障碍的方法。
• Facile, green, and functional group-tolerant reductions of carboxylic acids…in, or with, water
  作者：Karthik S. Iyer、Chandler Nelson、Bruce H. Lipshutz

  DOI：10.1039/d3gc00517h

  日期：——

  Facile reductions of carboxylic acids to aldehydes or alcohols can be effected under mild conditions upon initial conversion to their corresponding S-2-pyridyl thioesters. Upon treatment with a commercially available and air-stable nickel pre-catalyst and silane as a stoichiometric reductant, aldehydes are formed in moderate to good yields. Alternatively, the 1-pot conversion of acids to their thioester

  羧酸向醛或醇的轻松还原可以在温和条件下在初始转化为其相应的S -2-吡啶基硫酯时实现。在用市售且空气稳定的镍预催化剂和硅烷作为化学计量还原剂处理后，醛以中等到良好的收率形成。或者，可以将酸一锅法转化为其硫酯衍生物，然后在用硼氢化钠处理后还原为醇。使用这些绿色反应介质可以转化从高度功能化的酸到默克信息库中的离析物的各种起始材料。