S-(2-acetylphenyl) dimethylthiocarbamate | 22857-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-(2-acetylphenyl) dimethylthiocarbamate
• 英文别名: S-(2-acetylphenyl) N,N-dimethylcarbamothioate
• CAS: 22857-79-0
• 化学式: C₁₁H₁₃NO₂S
• 分子量: 223.296
• InChiKey: LRGOLQVUMFSKJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  250 °C(Press: 0.5 Torr)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-(2-acetylphenyl) dimethylthiocarbamate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 为溶剂， 生成 2-疏基苯乙酮
  参考文献：
  名称：

  Substituted 2-(3′,4′,5′-trimethoxybenzoyl)-benzo[b]thiophene derivatives as potent tubulin polymerization inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.05.068
• 作为产物：
  描述：

  1-(2-(tert-butylthio)phenyl)ethan-1-one 在 aluminum (III) chloride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 S-(2-acetylphenyl) dimethylthiocarbamate
  参考文献：
  名称：

  取代的苄硫醚：它们的环回复特性的合成和量子化学研究。

  摘要：

  开发了不需要快速真空热解的高度取代苯并硫代酸酯的灵活合成方法。这允许使用许多官能团和不可蒸发的分子。分离出高度稳定的衍生物。通过密度泛函方法评估了各种苯硫醚的分子轨道特性。比较了四元环的环还原机理与含氧类似物的环还原机理。

  DOI：

  10.1021/acs.orglett.0c01261

文献信息

• 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。
• Photothermal Conversion by Carbon Black Facilitates Aryl Migration by Photon‐Promoted Temperature Gradients
  作者：Megan E. Matter、Lejla Čamdžić、Erin E. Stache

  DOI：10.1002/anie.202308648

  日期：2023.10.2

  Photothermal conversion enables thermal gradients that facilitate high activation barrier reactions, such as the Newman Kwart Rearrangement. Substrates normally requiring bulk temperatures >250 °C are easily converted via visible light irradiation with short reaction times. Wavelength and intensity tunability enable selective product formation.

  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。
• Novel cyclization of S-(o-acetylaryl) dimethylthiocarbamates. A new synthesis of 3-hydroxybenzothiophenes and 2-hydroxythiochromones
  作者：C. K. Lau、Patrice C. Belanger、C. Dufresne、J. Scheigetz

  DOI：10.1021/jo00385a005

  日期：1987.5
• LAU C. K.; BELANGER P. C.; DUFRESNE C.; SCHEIGETZ J., J. ORG. CHEM., 52,(1987) N 9, 1670-1673
  作者：LAU C. K.、 BELANGER P. C.、 DUFRESNE C.、 SCHEIGETZ J.

  DOI：——

  日期：——
• US8927591B2
  申请人：——

  公开号：US8927591B2

  公开（公告）日：2015-01-06