O-2-nitrophenyl thiocarbamate | 833-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-2-nitrophenyl thiocarbamate
• 英文别名: o-(2-nitrophenyl)-N,N-dimethylthiocarbamate；2-nitrophenyl-N,N-dimethyl-O-thiocarbamate；O-(2-nitrophenyl) dimethylthiocarbamate；N,N-Dimethyl-O-<2-nitro-phenyl>-thiourethan；Dimethyl-thiocarbamidsaeure-O-(2-nitro-phenylester)；dimethyl-thiocarbamic acid O-(2-nitro-phenyl ester)；N,N-Dimethyl-thiocarbamidsaeure-O-(2-nitro-phenyl-ester)；O-(2-nitrophenyl) N,N-dimethylcarbamothioate
• CAS: 833-20-5
• 化学式: C₉H₁₀N₂O₃S
• 分子量: 226.256
• InChiKey: QOCIFGBOWJADLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-2-nitrophenyl thiocarbamate 在 sodium hydroxide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.17h， 生成 邻硝基苯硫酚
  参考文献：
  名称：

  A Comparison of Commercial Microwave Reactors for Scale-Up within Process Chemistry

  摘要：

  Seven commercially available microwave reactors designed for limited scale-up have been investigated using a highly reliable and robust reaction (the Newman-Kwart rearrangement). The use of a single reaction has enabled the comparison to be made across the range of different reactor types and scales. Overall, all reactors gave reliable scale-up from small scale, and performance equivalent to one another on large scale. A more detailed comparison between them is given in the concluding section.

  DOI：

  10.1021/op700186z
• 作为产物：
  描述：

  Oxo-phenylamino-acetyl azide 在 水 作用下， 生成 O-2-nitrophenyl thiocarbamate
  参考文献：
  名称：

  Thiocyanic and dithiocarbamic anhydrides and the process of making the same

  摘要：

  公开号：

  US02139935A1

文献信息

• Multicomponent Synthesis of Iminocoumarins via Rhodium-Catalyzed C—H Bond Activation
  作者：Zhan Chen、Shengnan Jin、Wenyao Jiang、Feimin Zhu、Yuqi Chen、Yingwei Zhao

  DOI：10.1021/acs.joc.0c01303

  日期：2020.8.21

  We herein establish a multicomponent annulation method for the synthesis of valuable iminocoumarins using aryl thiocarbamates, internal alkynes, and sulfonamides as starting materials, which are safe and readily available. The key step is a Rh-catalyzed and sulfur-directed C—H bond activation. Preliminary mechanistic investigations suggested that the nucleophilic attack of the sulfonamide on an active

  我们在本文中建立了一种多组分环合方法，用于以芳基硫代氨基甲酸酯，内部炔烃和磺酰胺为起始原料合成有价值的亚氨基香豆素，该方法安全且容易获得。关键步骤是Rh催化和硫导向的CH键活化。初步的机理研究表明，磺酰胺对活性亚胺阳离子的亲核攻击最终完成了亚胺片段。
• The Newman−Kwart Rearrangement:  A Microwave Kinetic Study
  作者：John P. Gilday、Philip Lenden、Jonathan D. Moseley、Brian G. Cox

  DOI：10.1021/jo702633g

  日期：2008.4.1

  The kinetic profile of the Newman−Kwart rearrangement has been evaluated using microwave heating. After first demonstrating equivalence between conventional convective heating and microwave heating, data was gathered and analyzed to determine the effects of substituent, solvent, and concentration on the reaction order. Reaction rate constants, Arrhenius constants, and activation energies have been

  Newman-Kwart重排的动力学曲线已使用微波加热进行了评估。在首先证明了常规对流加热和微波加热之间的等效性之后，收集并分析数据以确定取代基，溶剂和浓度对反应顺序的影响。已经确定了反应速率常数，阿累尼乌斯常数和活化能。反应速率显示出对取代基的强敏感性和对溶剂的适度敏感性。在高浓度下，反应顺序从先前报告的一级增加到混合的一级/二级反应。总的来说，对纽曼-科沃特重排的重新评估表明反应速率的顺序比以前认为的要复杂。此外，
• Microwave-mediated Newman–Kwart rearrangement in water
  作者：Ina Hoffmann、Jürgen Schatz

  DOI：10.1039/c6ra20676j

  日期：——

  For the first time the unimolecular Newman–Kwart rearrangement is performed in pure water.

  这是第一次在纯水中进行单分子Newman-Kwart重排。
• 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。
• Scaling-Out Pharmaceutical Reactions in an Automated Stop-Flow Microwave Reactor
  作者：Jonathan D. Moseley、Emily K. Woodman

  DOI：10.1021/op800091p

  日期：2008.9.19

  Six pharmaceutically relevant reactions were assessed for scale-out in an automated stop-flow microwave reactor. Daily throughputs of between 50 and 250 g were achieved at typical reaction concentrations; for more concentrated reactions, or with 24 h processing, productivity of 0.5-1.5 kg per day was achievable. This study confirms that the stop-flow approach in combination with rapid microwave heating can be equivalent to conventional continuous flow technology with comparable productivities.