茴三硫氚杂质1 | 22191-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 茴三硫氚杂质1
• 英文名称: 3-(4-methoxyphenyl)-N,N-dimethylpropanethioamide
• 英文别名: N,N-dimethyl-3-(p-methoxyphenyl)thiopropionamide；N,N-dimethyl-3-(4-methoxyphenyl)propanethioamide；N.N-Dimethyl-3-(4-methoxy-phenyl)-thiopropionsaeureamid；3-(4-methoxy-phenyl)-thiopropionic acid dimethylamide；N.N-Dimethyl-3-(4-methoxy-phenyl)-thiopropionamid；3-(4-Methoxy-phenyl)-thiopropionsaeure-dimethylamid
• CAS: 22191-62-4
• 化学式: C₁₂H₁₇NOS
• 分子量: 223.339
• InChiKey: MMUPONJDLVFFOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  240-250 °C(Press: 17 Torr)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  茴三硫氚杂质1 在 氢氧化钾 作用下， 生成 3-(4-甲氧基苯基)-丙酰胺
  参考文献：
  名称：

  Über neue und über verbesserte Wege zum Aufbau von pharmakologisch wichtigen Aminen V. Über die Synthese von Hydrastinin, Kotarnin und Lodal

  摘要：

  DOI：

  10.1002/ardp.19322700608
• 作为产物：
  描述：

  苯甲醚 在 二硫化碳 、 三氯化铝 、 sulfur 、 苯 作用下， 生成 茴三硫氚杂质1
  参考文献：
  名称：

  Kindler; Li, Chemische Berichte, 1941, vol. 74, p. 321,324

  摘要：

  DOI：

文献信息

• Nickel-catalyzed <i>C</i>-alkylation of thioamide, amides and esters by primary alcohols through a hydrogen autotransfer strategy
  作者：Peng Yang、Xiuhua Wang、Yu Ma、Yaxin Sun、Li Zhang、Jieyu Yue、Kaiyue Fu、Jianrong Steve Zhou、Bo Tang

  DOI：10.1039/d0cc06468h

  日期：——

  A simple catalyst of Ni(OAc)2 and P(t-Bu)3 enables selective C-alkylation of thioacetamides and primary acetamide with alcohols for the first time. Monoalkylation of thioamides, amides and t-butyl esters occurs in excellent yields (>95%). Mechanistic studies reveal that the reaction proceeds via a hydrogen autotransfer pathway.

  Ni（OAc）2和P（t-Bu）3的简单催化剂使硫代乙酰胺和伯乙酰胺与醇的选择性C-烷基化首次实现。硫代酰胺，酰胺和叔丁基酯的单烷基化以极高的收率（> 95％）发生。机理研究表明，反应通过氢自动转移途径进行。
• 3-芳基硫代丙酰胺衍生物的合成方法
  申请人：温州大学

  公开号：CN110590627B

  公开（公告）日：2022-01-14

  本发明涉及一种3‑芳基硫代丙酰胺衍生物的合成方法，包括以下步骤：以芳基丙炔衍生物为底物，碱为促进剂，单质硫作为硫源，在甲酰胺溶剂中，于100‑120℃下，搅拌反应12小时。本发明使用无臭、易得、廉价的单质硫作为硫源，具有原料简单易得，反应操作简单、条件相对温和、底物普适性广、产率较高、官能团兼容性良好的优点。
• Dimethylamine as the key intermediate generated in situ from dimethylformamide (DMF) for the synthesis of thioamides
  作者：Weibing Liu、Cui Chen、Hailing Liu

  DOI：10.3762/bjoc.11.187

  日期：——

  An improved and efficient method for the synthesis of thioamides is presented. For this transformation, dimethylamine as the key intermediate is generated in situ from dimethylformamide (DMF). All the tested substrates produced the desired products with excellent isolated yields.

  提出了一种改进和高效的合成硫代酰胺的方法。在这种转化中，二甲胺作为关键中间体从二甲甲酰胺（DMF）中原位生成。所有经过测试的底物均以优异的分离产率产生了期望的产物。
• Pd-catalyzed asymmetric α-allylic alkylation of thioamides
  作者：Bin Rong、Qin Yang、Yong Liu、Hong Xu、Yifan Hu、Xuejing Cheng、Baoguo Zhao

  DOI：10.1016/j.tetlet.2014.12.031

  日期：2015.1

  This Letter describes the first catalytic asymmetric alpha-allylic alkylation of thioamides. By using 5 mol % Pd-(R)-DM-BINAP complex as the chiral catalyst, various thioamides were efficiently alpha-allylic alkylated with 1,3-diarylallyl carbonates under mild conditions, affording a variety of alpha-substituted thioamides in good yields with high enantioselectivity and moderate diastereoselectivity. This work represents a useful and direct route to prepare chiral functionalized thioamides. (C) 2014 Elsevier Ltd. All rights reserved.
• Pd-catalyzed α-arylation of thioamides
  作者：Hailei Yu、Xuliang Liu、Lei Ding、Qin Yang、Bin Rong、Ang Gao、Baoguo Zhao、Haifeng Yang

  DOI：10.1016/j.tetlet.2013.03.114

  日期：2013.6

  Thioamides are unique and versatile synthetic building blocks with S, N, and alpha-C three adjacent nucleophile centers, however, they are rarely used as carbon nucleophiles for transition-metal-catalyzed C-C coupling reactions. This Letter describes the first Pd-catalyzed alpha-arylation of thioamides and demonstrated the feasibility of the application of thioamides in coupling chemistry. By the coupling process, a variety of alpha-arylated thioamides were prepared in moderate to good yields under mild reaction conditions, which provides an alternative way to access functionalized thioamides as well as a new synthetic transformation for thioamides. High chemoselectivity for thioamide over amide was observed in the reaction. (C) 2013 Elsevier Ltd. All rights reserved.