S-methyl N-(4-methylphenyl)thiocarbamate | 61578-87-8

• 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-methyl N-(4-methylphenyl)thiocarbamate
• 英文别名: S-methyl 4-tolylcarbamothioate；S-methyl p-tolylcarbamothioate；p-tolyl-thiocarbamic acid S-methyl ester；p-Tolyl-thiocarbamidsaeure-S-methylester；Carbamothioic acid, (4-methylphenyl)-, S-methyl ester；S-methyl N-(4-methylphenyl)carbamothioate
• CAS: 61578-87-8
• 化学式: C₉H₁₁NOS
• 分子量: 181.258
• InChiKey: AJEXMXBENVVQRF-UHFFFAOYSA-N

物化性质

• 熔点：
  102.1-103.5 °C
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-methyl N-(4-methylphenyl)thiocarbamate 、 氨 生成 甲硫醇 、 对甲苯基脲
  参考文献：
  名称：

  Will; Bielschowsky, Chemische Berichte, 1882, vol. 15, p. 1317

  摘要：

  DOI：
• 作为产物：
  描述：

  甲氧基二硫代甲酸甲酯 、 乙烷,三氯氟- 在 triethyl(methyl)ammonium S-methyl carbonodithioate 作用下， 以87%的产率得到S-methyl N-(4-methylphenyl)thiocarbamate
  参考文献：
  名称：

  通过O，S-二甲基碳二硫代伯芳基胺的甲硫羰基羰基化反应，快速，安全且廉价地制备S-甲基芳基氨基甲酸酯

  摘要：

  ø，小号二甲基carbonodithioate提出作为可在伯烷基胺的methylthiocarbonylation给要使用的合适的和安全地处理试剂小号甲基arylcarbamothioates。最佳条件涉及一步步骤，该步骤在无溶剂系统中于45°C的条件下，在作为反应促进剂的三乙基（甲基）铵S-甲基碳二硫代硫酸盐存在下进行。获得的标题产物的收率纯净，除了一个例外，在72％至91％之间变化（所考虑的12个实例的平均收率为83％）。副产物S，S-二甲基二硫代碳酸盐也是有价值的试剂。 O，S-二甲基碳二硫代酸酯-芳基氨基甲硫酸酯-硫羰基化-S，S-二甲基碳二硫代酸酯-甲苯-2,4-二硫代氨基甲酸S，S-二甲基酯

  DOI：

  10.1055/s-0029-1219226

文献信息

• Synthesis ofN-arylS-alkylthiocarbamates
  作者：Mamoru Koketsu、Chikashi Kobayashi、Hideharu Ishihara

  DOI：10.1002/hc.10163

  日期：——

  Several N-aryl S-alkylthiocarbamates were synthesized by reactions of isocyanates with LiAlHSH and then with alkyl halides. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:374–378, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10163

  通过异氰酸酯与 LiAlHSH 然后与烷基卤反应合成了几种 N-芳基 S-烷基硫代氨基甲酸酯。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:374–378, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10163
• Potent Inhibitory Effects of N-Aryl S-Alkylthiocarbamate Derivatives on the Dopa Oxidase Activity of Mushroom Tyrosinase
  作者：Kun Ho Lee、Mamoru Koketsu、Sang Yoon Choi、Kang Jin Lee、Pyeongjae Lee、Hideharu Ishihara、Sun Yeou Kim

  DOI：10.1248/cpb.53.747

  日期：——

  This study reports the potent inhibitory effect of N-aryl S-alkylthiocarbamate derivatives on mushroom tyrosinase (MT) activity. N-Aryl S-alkylthiocarbamate derivatives were found to exhibit a potent inhibitory effect on the dopa (3,4-dihydroxyphenylalanine) oxidase activity of mushroom tyrosinase. Most of the N-aryl S-alkylthiocarbamate derivatives (compounds from A to J) exhibited higher inhibitory effects than kojic acid (IC50=318 μm), a well known tyrosinase inhibitor. Tyrosinase was the most inhibited by S-phenetyl N-phenylthiocarbamate (compound E, IC50=7.25 μM), and this inhibition was 44 times stronger than that of kojic acid. Compound E exhibited 95.0% of inhibition at 100 μM. A kinetic study of MT inhibition by compound E using the Lineweaver–Burk plots analysis was performed. And the kinetics profiles observed suggest that compound E competitively inhibits MT.

  本研究报告了N-芳基S-烷基硫代氨基甲酸酯衍生物对蘑菇酪氨酸酶（MT）活性的强抑制作用。发现N-芳基S-烷基硫代氨基甲酸酯衍生物对蘑菇酪氨酸酶的多巴（3,4-二羟基苯丙氨酸）氧化酶活性具有强抑制效果。大多数N-芳基S-烷基硫代氨基甲酸酯衍生物（A到J化合物）显示出比已知的酪氨酸酶抑制剂桂皮酸更强的抑制效果（IC50=318 μM）。S-苯乙基N-苯基硫代氨基甲酸酯（E化合物）对酪氨酸酶的抑制最为显著，其IC50为7.25 μM，该抑制强度是桂皮酸的44倍。E化合物在100 μM时显示出95.0%的抑制率。利用Lineweaver–Burk图分析进行了E化合物对MT抑制的动力学研究，观察到的动力学特征表明E化合物是通过竞争性抑制MT的。
• Liebermann; Natanson, Justus Liebigs Annalen der Chemie, 1881, vol. 207, p. 162
  作者：Liebermann、Natanson

  DOI：——

  日期：——
• Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: a route to diversely substituted S-alkylcarbamothioates
  作者：Abdallah Larbi Doukara、Mohammed Amine Mehdid、Ayada Djafri、Federico Andreoli、Nicolas Vanthuyne、Christian Roussel

  DOI：10.1016/j.tet.2010.01.020

  日期：2010.3

  A new route to S-alkylcarbamothioates is disclosed. In a first step, N-(2-aminophenyl)-4-methyl-thiazolin-2-thione is transformed into a mono- or disubstituted urea at nitrogen, and then in a second step, alkylated at sulfur. The resulting salts, after treatment with a base, gave S-alkylcarbamothioates in high isolated yields together with 3-methyl[1,3]thiazolo[3,2-a]benzimidazole under very mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.
• Will; Bielschowsky, Chemische Berichte, 1882, vol. 15, p. 1317
  作者：Will、Bielschowsky

  DOI：——

  日期：——