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

• 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。
• 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
• 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