N-(4-methoxyphenyl)thiophene-2-carbothioamide | 107366-74-5

• 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: N-(4-methoxyphenyl)thiophene-2-carbothioamide
• 英文别名: 2-Thiophenecarbothioamide, N-(4-methoxyphenyl)-
• CAS: 107366-74-5
• 化学式: C₁₂H₁₁NOS₂
• 分子量: 249.357
• InChiKey: JEBMQJFCOBWCAG-UHFFFAOYSA-N

物化性质

• 熔点：
  129.0-130.5 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  376.6±48.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲氧苯胺 、 phenyl dithio-2-thiophenate 以 乙腈 为溶剂， 生成 N-(4-methoxyphenyl)thiophene-2-carbothioamide
  参考文献：
  名称：

  Aminolysis of aryl dithio-2-thiophenates and dithio-2-furoates in acetonitrile

  摘要：

  The aminolyses of the title substrates with anilines and benzylamines are investigated in acetonitrile. A clean second-order kinetics is obtained with a first-order rate law in the amine concentration, which is uncomplicated by the fast proton transfer step. The large magnitude of rho(z) (rho(1g)) as well as rho(x) (rho(nuc)) together with relatively large positive p(xz) values is consistent with a stepwise mechanism in which thiophenolate ion expulsion from the intermediate is rate limiting. For the reactions of aryl dithio-2-thiophenates with benzylamines the magnitude of rho(x) and rho(z) values is relatively smaller suggesting that both the addition and expulsion of thiophenolate are partially rate determining. Relatively large secondary kinetic isotope effects, k(H)/k(D) greater than or equal to 1.7, with deuterated nucleophiles, support involvement a concurrent proton transfer to the departing thiophenolate ion in the transition state. (C) 1998 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1998)30:11<849::aid-kin7>3.0.co;2-v

文献信息

• A metal-free and a solvent-free synthesis of thio-amides and amides: an efficient Friedel–Crafts arylation of isothiocyanates and isocyanates
  作者：Begur Vasanthkumar Varun、Ankush Sood、Kandikere Ramaiah Prabhu

  DOI：10.1039/c4ra12944j

  日期：——

  A rapid, metal-free and solvent-free (very low loading of solvent in few cases) reaction conditions for synthesizing thioamides and amides using a Bronsted super acid such as triflic acid has been developed.

  一种快速、无金属、无溶剂（在少数情况下溶剂负载量非常低）的反应条件已经开发出来，用于合成硫代酰胺和酰胺，使用三氟甲磺酸等Bronsted超强酸。
• A friedel-crafts synthesis of m-substituted thiophenecarbothioamides
  作者：Tadeusz Jagodziński、Elżbieta Jagodzińska、Zygfryd Jabłoński

  DOI：10.1016/s0040-4020(01)87336-1

  日期：1986.1
• JAGODZINSKI T.; JAGODZINSKA E.; JABLONSKI Z., TETRAHEDRON, 42,(1986) N 13, 3683-3688
  作者：JAGODZINSKI T.、 JAGODZINSKA E.、 JABLONSKI Z.

  DOI：——

  日期：——
• Aminolysis of aryl dithio-2-thiophenates and dithio-2-furoates in acetonitrile
  作者：Hyuck Keun Oh、So Young Woo、Chul Ho Shin、Ikchoon Lee

  DOI：10.1002/(sici)1097-4601(1998)30:11<849::aid-kin7>3.0.co;2-v

  日期：——

  The aminolyses of the title substrates with anilines and benzylamines are investigated in acetonitrile. A clean second-order kinetics is obtained with a first-order rate law in the amine concentration, which is uncomplicated by the fast proton transfer step. The large magnitude of rho(z) (rho(1g)) as well as rho(x) (rho(nuc)) together with relatively large positive p(xz) values is consistent with a stepwise mechanism in which thiophenolate ion expulsion from the intermediate is rate limiting. For the reactions of aryl dithio-2-thiophenates with benzylamines the magnitude of rho(x) and rho(z) values is relatively smaller suggesting that both the addition and expulsion of thiophenolate are partially rate determining. Relatively large secondary kinetic isotope effects, k(H)/k(D) greater than or equal to 1.7, with deuterated nucleophiles, support involvement a concurrent proton transfer to the departing thiophenolate ion in the transition state. (C) 1998 John Wiley & Sons, Inc.