o-(2-acetylphenyl) dimethylthiocarbamate | 14786-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: o-(2-acetylphenyl) dimethylthiocarbamate
• 英文别名: O-(2-acetylphenyl) N,N-dimethylcarbamothioate；N,N-Dimethyl-thiocarbamidsaeure-O-(2-acetyl-phenylester)；O-(2-acetylphenyl) dimethylcarbamothioate
• CAS: 14786-83-5
• 化学式: C₁₁H₁₃NO₂S
• 分子量: 223.296
• InChiKey: JHTOVEBCZYGJCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  o-(2-acetylphenyl) dimethylthiocarbamate 在 carbon 作用下， 以83 %的产率得到S-(2-acetylphenyl) dimethylthiocarbamate
  参考文献：
  名称：

  炭黑的光热转换通过光子促进的温度梯度促进芳基迁移

  摘要：

  光热转换可实现热梯度，从而促进高活化势垒反应，例如纽曼夸特重排。通常需要> 250 °C 整体温度的基材可以通过可见光照射轻松转换，反应时间短。波长和强度的可调性能够选择性地形成产物。

  DOI：

  10.1002/anie.202308648
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 二甲氨基硫代甲酰氯 在 三乙烯二胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以75 %的产率得到o-(2-acetylphenyl) dimethylthiocarbamate
  参考文献：
  名称：

  炭黑的光热转换通过光子促进的温度梯度促进芳基迁移

  摘要：

  光热转换可实现热梯度，从而促进高活化势垒反应，例如纽曼夸特重排。通常需要> 250 °C 整体温度的基材可以通过可见光照射轻松转换，反应时间短。波长和强度的可调性能够选择性地形成产物。

  DOI：

  10.1002/anie.202308648

文献信息

• Divergent Synthesis of Disulfanes and Benzenesulfonothioates Bearing 2-Aminofurans From N-Tosylhydrazone-Bearing Thiocarbamates
  作者：Shaoyu Mai、Qiuling Song

  DOI：10.1002/anie.201704091

  日期：2017.6.26

  An efficient and convenient synthesis of valuable disulfanes and benzenesulfonothioates, having a 2-aminofuran framework, has been developed by employing a copper-catalyzed transformation of readily available N-tosylhydrazone-bearing thiocarbamates. This method features an inexpensive metal catalyst, mild reaction conditions, good functional-group tolerance, short reaction times, and delivers valuable

  通过使用容易获得的带有N-甲苯磺酰hydr的硫代氨基甲酸酯的铜催化转化，已经开发了具有2-氨基呋喃骨架的有价值的二硫烷和苯硫基硫代磺酸盐的有效和方便的合成方法。该方法具有廉价的金属催化剂，温和的反应条件，良好的官能团耐受性，较短的反应时间，并提供了有价值且复杂的产品。从含N-甲苯磺酰hydr的硫代氨基甲酸酯生成的铜卡宾被提议作为该转化的关键中间体，并引发随后的级联反应。值得注意的是，从N-甲苯磺酰released释放的Ts阴离子还可以用作亲核试剂，因此在受控条件下形成了苯磺基硫代磺酸盐。
• THIOCHROMENE DERIVATIVES AS HIF HYDROXYLASE INHIBITORS
  申请人：Ho Wen-Bin

  公开号：US20110305776A1

  公开（公告）日：2011-12-15

  The present invention relates to novel compounds, methods, and compositions capable of decreasing HIF hydroxylase enzyme activity, thereby increasing the stability and/or activity of hypoxia inducible factor (HIF).

  本发明涉及新型化合物、方法和组合物，能够降低HIF羟化酶酶活性，从而增加缺氧诱导因子（HIF）的稳定性和/或活性。
• The Conversion of Phenols to Thiophenols via Dialkylthiocarbamates¹
  作者：Melvin S. Newman、Harold A. Karnes

  DOI：10.1021/jo01350a023

  日期：1966.12
• Palladium-Catalyzed Intramolecular Oxidative CH Sulfuration of Aryl Thiocarbamates
  作者：Yingwei Zhao、Yinjun Xie、Chungu Xia、Hanmin Huang

  DOI：10.1002/adsc.201400306

  日期：2014.8.11

  AbstractA palladium‐catalyzed intramolecular CH bond sulfuration reaction of aryl thiocarbamates has been developed. This strategy provides a new route to benzo[d][1,3]oxathiol‐2‐ones with tolerance of a wide range of substituents. Mechanistic studies suggested that the CH activation–sulfuration to afford 2‐imino‐1,3‐benzoxathiole intermediate might involve an electrophilic palladation process.magnified image
• Substituted 2-(3′,4′,5′-trimethoxybenzoyl)-benzo[b]thiophene derivatives as potent tubulin polymerization inhibitors
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Olga Cruz-Lopez、Manlio Tolomeo、Stefania Grimaudo、Antonietta Di Cristina、Maria Rosaria Pipitone、Jan Balzarini、Andrea Brancale、Ernest Hamel

  DOI：10.1016/j.bmc.2010.05.068

  日期：2010.7

  The central role of microtubules in cell division and mitosis makes them a particularly important target for anticancer agents. On our early publication, we found that a series of 2-(3',4',5'-trimethoxybenzoyl)-3-aminobenzo[b]thiophenes exhibited strong antiproliferative activity in the submicromolar range and significantly arrested cells in the G2-M phase of the cell cycle and induced apoptosis. In order to investigate the importance of the amino group at the 3-position of the benzo[b] thiophene skeleton, the corresponding 3-unsubstituted and methyl derivatives were prepared. A novel series of inhibitors of tubulin polymerization, based on the 2-(3,4,5-trimethoxybenzoyl)-benzo[b] thiophene molecular skeleton with a methoxy substituent at the C-4, C-5, C-6 or C-7 position on the benzene ring, was evaluated for antiproliferative activity against a panel of five cancer cell lines, for inhibition of tubulin polymerization and for cell cycle effects. Replacing the methyl group at the C-3 position resulted in increased activity compared with the corresponding 3-unsubstituted counterpart. The structure-activity relationship established that the best activities were obtained with the methoxy group placed at the C-4, C-6 or C-7 position. Most of these compounds exhibited good growth inhibition activity and arrest K562 cells in the G2-M phase via microtubule depolymerization. (C) 2010 Elsevier Ltd. All rights reserved.