S-2-nitrophenyl thiocarbamate | 13511-84-7

• 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: S-2-nitrophenyl thiocarbamate
• 英文别名: S-(2-nitrophenyl)-N,N-dimetylthiocarbamate；S-(2-nitrophenyl)-N,N-dimethylcarbamothioate；2-nitrophenyl-N,N-dimethyl-S-thiocarbamate；S-(2-nitrophenyl) dimethylthiocarbamate；N,N-Dimethyl-thiocarbamidsaeure-S-<2-nitro-phenylester>；(o-Nitrophenyl)-N,N-dimethylthiocarbamat；S-(2-nitrophenyl) N,N-dimethylcarbamothioate
• CAS: 13511-84-7
• 化学式: C₉H₁₀N₂O₃S
• 分子量: 226.256
• InChiKey: OWVWODLSACPOIP-UHFFFAOYSA-N

物化性质

• 熔点：
  30-32 °C
• 沸点：
  343.1±44.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  91.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-2-nitrophenyl thiocarbamate 在 sodium hydroxide 、 盐酸 作用下， 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：

  O-2-nitrophenyl thiocarbamate 以 various solvent(s) 为溶剂， 生成 S-2-nitrophenyl thiocarbamate
  参考文献：
  名称：

  Newman-Kwart重排：微波动力学研究

  摘要：

  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，

  DOI：

  10.1021/jo702633g

文献信息

• 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。
• Palladium−Copper Catalyzed Synthesis of Benzofused Heterocycles with Two Heteroatoms: Novel and Highly Regio- and Stereoselective Syntheses of (<i>E</i>)-2-(2-Arylvinyl)-3-tosyl-2,3-dihydro-1,3-benzothiazoles and (<i>E</i>)-2-Alkyl(aryl)idene-3,4-dihydro-2<i>H</i>-1,4-benzothiazines
  作者：Nitya G. Kundu、Bidisha Nandi

  DOI：10.1021/jo001783+

  日期：2001.6.1

  A highly novel, general, and convenient palladium and copper-catalyzed procedure has been developed for the synthesis of (E)-2-(2-arylvinyl)-3-tosyl-2,3-dihydro-1,3-benzothiazoles 28-40. 3-(2-Aminophenylthio)prop-1-yne 1 reacts with aryl iodides 2-14 under palladium-copper catalysis to yield the disubstituted alkynes 15-27 which after tosylation undergo a novel cyclization with CuI in the presence

  已开发出一种高度新颖，通用且方便的钯和铜催化方法，用于合成（E）-2-（2-芳基乙烯基）-3-甲苯磺酰基-2,3-二氢-1,3-苯并噻唑28- 40 3-（2-氨基苯硫基）丙-1-炔1在钯-铜催化下与芳基碘化物2-14反应生成双取代炔烃15-27，甲苯磺酸化后，在THF中在三乙胺存在下用CuI进行新型环化反应（E）-2-（2-芳基乙烯基）-3-甲苯基-2,3-二氢-1,3-苯并噻唑28-40，而不是预期的3-亚烷基-4-甲苯基-3,4-二氢-2H -1,4-苯并噻嗪41.反应具有很高的区域选择性和立体选择性。还报道了2-（2-芳基乙基）-3-甲苯基苯并噻唑啉42-47、2-（2-芳基乙烯基）苯并噻唑48-54和具有潜在生物学重要性的新型5-取代尿嘧啶衍生物55的合成。同样，S- [2-（N-prop-2'-炔基）氨基苯基] -N，N-二甲基硫代氨基甲酸酯58与芳基碘化物的钯铜催化的芳基化反
• 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.
• The Conversion of Phenols to Thiophenols via Dialkylthiocarbamates¹
  作者：Melvin S. Newman、Harold A. Karnes

  DOI：10.1021/jo01350a023

  日期：1966.12