2-((3-methoxyphenyl)thio)benzonitrile

• 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-((3-methoxyphenyl)thio)benzonitrile
• 英文别名: 2-(3-Methoxyphenyl)sulfanyl-benzonitrile；2-(3-methoxyphenyl)sulfanylbenzonitrile
• 化学式: C₁₄H₁₁NOS
• 分子量: 241.313
• InChiKey: CBWCTSNMGZUTIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  C₇H₇O₂S^(1-) 在 lithium chloro-isopropyl-magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2-((3-methoxyphenyl)thio)benzonitrile
  参考文献：
  名称：

  使用亚砜试剂作为硫双阳离子当量的一锅三组分组装硫化物

  摘要：

  我们报告了通过利用亚砜试剂作为形式的硫双标等价物来一锅三组分合成硫化物。我们的方案由三个简单的化学操作组成，涉及两种格氏试剂和三甲基氯硅烷 (TMSCl)，依次形成磺酸根阴离子、磺酸酯和硫化物。我们展示了多种可偶联的格氏试剂，从而可以模块化、无硫醇合成硫化物，包括二烯基和烯基-炔基硫化物。

  DOI：

  10.1021/acs.orglett.3c02301

文献信息

• Facile synthesis of 1,2-thiobenzonitriles <i>via</i> Cu-catalyzed denitrogenative radical coupling reaction
  作者：Yao Zhou、Ya Wang、Yixian Lou、Qiuling Song

  DOI：10.1039/c9cc05099j

  日期：——

  A Cu-catalyzed synthesis of 1,2-thiobenzonitriles via oxidative C–N cleavage of 3-aminoindazoles followed by radical coupling with thiols is developed. A diverse array of 1,2-thiobenzonitriles were obtained in good yields with wide substrate scope. Notably, this is the first example of denitrogenative radical coupling with 3-aminoindazoles.

  的Cu-催化的1,2- thiobenzonitriles合成通过3- aminoindazoles接着用硫醇自由基偶合的氧化C-N裂解显影。以良好的收率和宽的底物范围获得了各种各样的1,2-硫代苄腈。值得注意的是，这是脱氮自由基与3-氨基吲唑偶联​​的第一个例子。
• Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹
  作者：J. Scott Sawyer、Elisabeth A. Schmittling、Jayne A. Palkowitz、William J. Smith

  DOI：10.1021/jo980800g

  日期：1998.9.1

  An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable S-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.
• Synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6
  作者：Elisabeth A. Schmittling、J. Scott Sawyer

  DOI：10.1021/jo00064a004

  日期：1993.6

  An efficient alternative to the copper-catalyzed synthesis (Ullmann ether synthesis) of diaryl ethers, diaryl thioethers, and diarylamines involving the potassium fluoride-alumina-mediated addition of a phenol, thiophenol, or an aniline to 2- or 4-fluorobenzonitriles catalyzed by 18-crown-6 is described.
• Substituted phenyl phenol leukotriene antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0544488B1

  公开（公告）日：1998-03-11
• One-Pot, Three-Component Assembly of Sulfides Using a Sulfoxide Reagent as a Sulfur Dication Equivalent
  作者：Fumito Saito、Simon Euteneuer

  DOI：10.1021/acs.orglett.3c02301

  日期：2023.8.18

  We report a one-pot, three-component synthesis of sulfides by exploiting a sulfoxide reagent as a formal sulfur dication equivalent. Our protocol consists of three simple chemical operations involving two Grignard reagents and trimethylsilyl chloride (TMSCl) to sequentially form sulfenate anions, sulfenate esters, and sulfides. We demonstrate a wide range of Grignard reagents to be coupled, thereby

  我们报告了通过利用亚砜试剂作为形式的硫双标等价物来一锅三组分合成硫化物。我们的方案由三个简单的化学操作组成，涉及两种格氏试剂和三甲基氯硅烷 (TMSCl)，依次形成磺酸根阴离子、磺酸酯和硫化物。我们展示了多种可偶联的格氏试剂，从而可以模块化、无硫醇合成硫化物，包括二烯基和烯基-炔基硫化物。