2-(naphthalen-2-ylthio)-1-phenylethan-1-ol | 101722-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalen-2-ylthio)-1-phenylethan-1-ol
• 英文别名: 2-Naphthalen-2-ylsulfanyl-1-phenylethanol
• CAS: 101722-95-6
• 化学式: C₁₈H₁₆OS
• 分子量: 280.39
• InChiKey: ORGWNSBLLHYGEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[(naphthalen-2-yl)sulfanyl]-1-phenylethanone 在 lithium aluminium tetrahydride 作用下， 生成 2-(naphthalen-2-ylthio)-1-phenylethan-1-ol
  参考文献：
  名称：

  Notes- Reaction of Styrene Oxide with 2-Naphthalenethiol

  摘要：

  DOI：

  10.1021/jo01089a617

文献信息

• Solvent-mediated switching between oxidative addition and addition–oxidation: access to β-hydroxysulfides and β-arylsulfones by the addition of thiols to olefins in the presence of Oxone
  作者：Soumen Payra、Navin Yadav、Jarugu Narasimha Moorthy

  DOI：10.1039/d1nj04892a

  日期：——

  The reaction between aryl olefins and thiols in the presence of Oxone in toluene–water (9 : 1, v/v) affords β-hydroxy-2-arylethyl aryl sulfides smoothly by the interception of intermediary thiyl radicals with aryl olefins; the former are generated by the oxidation of thiols with Oxone in a biphasic medium. However, the change of the solvent system to acetonitrile–water facilitates a nonradical and

  芳基烯烃和硫醇在 Oxone 存在下在甲苯-水 (9 : 1, v/v) 中的反应通过拦截中间硫基自由基与芳基烯烃顺利地提供 β-羟基-2-芳基乙基芳基硫化物；前者是通过在双相介质中用 Oxone 氧化硫醇产生的。然而，将溶剂系统改为乙腈 - 水促进了非自由基和协同途径，仅通过串联点击反应，然后氧化。本质上，在甲苯-水介质中促进了“氧化加成”，而在乙腈-水介质中促进了“加成-氧化”。鉴于 Oxone 易于获得、环境友好且价格低廉，溶剂介导的转换构成了对两种不同产品的轻松直接访问，即 β-羟基-2-芳基乙基芳基硫化物和 2-芳基乙基芳基砜。
• Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System
  作者：Jiawei Huang、Xiaoman Li、Liang Xu、Yu Wei

  DOI：10.1021/acs.joc.2c02856

  日期：2023.3.3

  A three-component oxychalcogenation reaction, from alkenes, diselenides/thiophenols, and H2O/alcohols, has been realized herein. Tetrabutylammonium tribromide (TBATB) and dimethylsulfoxide (DMSO) are utilized as the catalyst and the terminal oxidant, respectively, to enable this difunctionalization transformation. The metal-free reaction system shows good functional group compatibility, providing a

  本文实现了烯烃、二硒化物/苯硫酚和 H 2 O/醇的三组分氧硫属化反应。四丁基三溴化铵 (TBATB) 和二甲基亚砜 (DMSO) 分别用作催化剂和末端氧化剂，以实现这种双官能化转化。无金属反应体系显示出良好的官能团相容性，为获得β-羟基或β-烷氧基有机硫族化合物提供了统一实用的途径。
• 10.1021/acs.joc.4c00276
  作者：Yu, Enbo、Li, Jun、Wang, Yue、Chen, Ya、Xiao, Fuhong、Deng, Guo-Jun

  DOI：10.1021/acs.joc.4c00276

  日期：——

  A copper-catalyzed three-component coupling reaction of styrene oxide, aryl iodide, and carbon disulfide for the construction of β-hydroxysulfides has been developed. In this process, readily available CS2 was used as the sulfur source to construct C–S bonds for the synthesis of phenyl-β-hydroxysulfides and (benzo[d]thiazol)-β-hydroxysulfides. This process features mild reaction conditions, simple

  开发了用于构建β-羟基硫化物的铜催化氧化苯乙烯、芳基碘和二硫化碳的三组分偶联反应。在此过程中，使用容易获得的CS 2作为硫源来构建C-S键，用于合成苯基-β-羟基硫化物和(苯并[ d ]噻唑)-β-羟基硫化物。该工艺反应条件温和、操作简单、底物范围广（>50例）。
• Rapid, benign, and additive-free thiolysis of epoxides under ultrasonic/aqueous conditions
  作者：Mohammad M. Mojtahedi、Sajad Khalili

  DOI：10.1080/17415993.2014.909814

  日期：2014.7.4

  An environmentally friendly and efficient procedure is developed for ring opening of various epoxides with thiols under non-thermal conditions. Reactions take place by ultrasonic irradiation of the two reactants suspended in an additive-free aqueous medium. Consequently, high-yield formation of various beta-hydroxy sulfides is quickly observed.[GRAPHICS].
• Light-Promoted and Tertiary-Amine-Assisted Hydroxysulfenylation of Alkenes: Selective and Direct One-Pot Synthesis of β-Hydroxysulfides
  作者：Jing Shi、Xue-Wang Gao、Qing-Xiao Tong、Jian-Ji Zhong

  DOI：10.1021/acs.joc.1c01610

  日期：2021.9.17