5-methoxy-2-(methylthio)aniline | 19397-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-methoxy-2-(methylthio)aniline
• 英文别名: 5-Methoxy-2-(methylthio)benzenamine；5-methoxy-2-methylsulfanylaniline
• CAS: 19397-84-3
• 化学式: C₈H₁₁NOS
• 分子量: 169.247
• InChiKey: JOCOJFJMXKVBJH-UHFFFAOYSA-N

物化性质

• 沸点：
  289.6±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-(methylthio)aniline 在 sodium formate 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  2-异氰基芳基硫醚与醇的金属自由基级联环化：2-羟烷基苯并噻唑的合成

  摘要：

  已经开发了 2-异氰基芳基硫醚与醇的金属自由基级联环化。它为合成多种底物范围广、官能团耐受性好、产率适中的2-羟烷基苯并噻唑提供了一种新颖有效的方法。

  DOI：

  10.1016/j.tet.2022.132927
• 作为产物：
  描述：

  2-甲基-5-甲氧基苯并噻唑 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 乙醇 、 乙二醇 为溶剂， 反应 3.25h， 生成 5-methoxy-2-(methylthio)aniline
  参考文献：
  名称：

  2-(Anilinomethyl)imidazolines as α₁ Adrenergic Receptor Agonists:  the Discovery of α_1a Subtype Selective 2‘-Alkylsulfonyl-Substituted Analogues

  摘要：

  A series of 2'-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of alpha-adrenergic receptor subtypes alpha(1a), alpha(1b), alpha(1d), alpha(2a), and alpha(2c). Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited alpha(1a) subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for alpha(1a) vs all other subtypes.

  DOI：

  10.1021/jm000542r

文献信息

• Dual role of ethyl bromodifluoroacetate in the formation of fluorine-containing heteroaromatic compounds
  作者：Xingxing Ma、Shaoyu Mai、Yao Zhou、Gui-Juan Cheng、Qiuling Song

  DOI：10.1039/c8cc04298e

  日期：——

  BrCF2COOEt plays a dual role as a C1 synthon and a difluoroalkylating reagent for the first time. Mechanistic studies supported by DFT calculations suggest that a base plays an active role in the formation of the key intermediate isocyanides generated in situ from primary amines and difluorocarbene.

  描述了一种有效的一锅级联过程，该过程通过将BrCF 2 COOEt与伯胺进行空前的四次裂解以提供有价值的含氟杂环，其中BrCF 2 COOEt首次扮演了C1合成子和二氟烷基化试剂的双重角色。DFT计算支持的机理研究表明，碱在伯胺和二氟卡宾就地生成的关键中间异氰酸酯的形成中起着积极作用。
• 2-(Anilinomethyl)imidazolines as α₁ Adrenergic Receptor Agonists:  the Discovery of α₁_a Subtype Selective 2‘-Alkylsulfonyl-Substituted Analogues
  作者：Stephen J. Hodson、Michael J. Bishop、Jason D. Speake、Frank Navas、Deanna T. Garrison、Eric C. Bigham、David L. Saussy,、James A. Liacos、Paul E. Irving、M. Jeffrey Gobel、Bryan W. Sherman

  DOI：10.1021/jm000542r

  日期：2002.5.1

  A series of 2'-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of alpha-adrenergic receptor subtypes alpha(1a), alpha(1b), alpha(1d), alpha(2a), and alpha(2c). Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited alpha(1a) subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for alpha(1a) vs all other subtypes.
• Metal-free radical cascade cyclization of 2-isocyanoaryl thioethers with alcohols: Synthesis of 2-hydroxyalkyl benzothiazoles
  作者：Dengqi Xue、Qianwei Ge、Xiecheng Zhi、Siyu Song、Liming Shao

  DOI：10.1016/j.tet.2022.132927

  日期：2022.8

  A metal-free radical cascade cyclization of 2-isocyanoaryl thioethers with alcohols has been developed. It provides a novel and effective method to synthesize diverse 2-hydroxyalkyl benzothiazoles with broad substrate scope, good functional group tolerance and moderate to excellent yields.

  已经开发了 2-异氰基芳基硫醚与醇的金属自由基级联环化。它为合成多种底物范围广、官能团耐受性好、产率适中的2-羟烷基苯并噻唑提供了一种新颖有效的方法。