phenyl-thiocarbamic acid (S)-propyl ester | 17425-08-0

• 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: phenyl-thiocarbamic acid (S)-propyl ester
• 英文别名: phenyl-thiocarbamic acid S-propyl ester；phenylthiocarbamic acid S-propyl ester；S-n-propyl N-phenylthiocarbamate；S-propyl N-phenylthiocarbamate；phenyl-thiocarbamic acid S-propyl ester；Phenyl-thiocarbamidsaeure-S-propylester；Carbamothioic acid, phenyl-, S-propyl ester；S-propyl N-phenylcarbamothioate
• CAS: 17425-08-0
• 化学式: C₁₀H₁₃NOS
• 分子量: 195.285
• InChiKey: YVEDOVQPNWRWPV-UHFFFAOYSA-N

物化性质

• 熔点：
  76.5 °C
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 phenyl-thiocarbamic acid (S)-propyl ester 在 氯化亚砜 作用下， 生成 S-propyl N-(chloromethyl)-N-phenylcarbamothioate
  参考文献：
  名称：

  CH566971

  摘要：

  公开号：
• 作为产物：
  描述：

  异氰酸苯酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 LiAlHSH 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到phenyl-thiocarbamic acid (S)-propyl ester
  参考文献：
  名称：

  Potent Inhibitory Effects of N-Aryl S-Alkylthiocarbamate Derivatives on the Dopa Oxidase Activity of Mushroom Tyrosinase

  摘要：

  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。

  DOI：

  10.1248/cpb.53.747

文献信息

• A Novel One-Pot Solvent-Free, Triethylamine-Assisted, Selenium-Catalyzed Synthesis of Thiocarbamates from Nitroarenes, Carbon Monoxide, and Thiols
  作者：Shiwei Lu、Xiaopeng Zhang

  DOI：10.1055/s-2005-869839

  日期：——

  A novel one-pot solvent-free synthesis of a series of thiocarbamates is reported. Nitroarenes, carbon monoxide, and thiols are the starting materials, with cheap element selenium as catalyst; this method offers a simple access to thiocarbamates mostly in moderate to good yields. The selenium catalyst can be easily recovered and recycled.

  报道了一种新颖的无溶剂一锅法合成一系列硫代氨基甲酸酯的方法。以硝基芳烃、一氧化碳和硫醇为原料，廉价元素硒为催化剂；该方法可便捷地合成硫代氨基甲酸酯，产率大多为中等到良好。硒催化剂易于回收再利用。
• A Selenium-Catalysed Synthesis of Thiocarbamates from Nitroarenes, Carbon Monoxide and Thiols under Mild Conditions
  作者：Xiao-Peng Zhang、Shi-Wei Lu

  DOI：10.3184/030823408x360346

  日期：2008.10

  An improved method for the selenium-catalysed synthesis of thiocarbamates under mild conditions has been developed. With acetone as solvent, the one-pot selenium-catalysed carbonylation of nitroarenes and thiols with carbon monoxide proceeds smoothly at atmospheric pressure and ambient temperature.

  已开发出一种在温和条件下硒催化合成硫代氨基甲酸酯的改进方法。以丙酮为溶剂，一锅硒催化硝基芳烃和硫醇与一氧化碳的羰基化反应在常压常温下顺利进行。
• ISOTHIOCYANATE PRODUCTION METHOD, COMPOSITION FOR TRANSPORTING AND STORING N-SUBSTITUTED O-SUBSTITUTED THIOCARBAMATE, AND ISOTHIOCYANATE COMPOSITION
  申请人：ASAHI KASEI CHEMICALS CORPORATION

  公开号：US20160016901A1

  公开（公告）日：2016-01-21

  The present invention relates to an isothiocyanate production method using an organic primary amine and thiourea as starting materials; to a composition for transporting and storing an N-substituted O-substituted thiocarbamate that includes an N-substituted O-substituted thiocarbamate and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the carbamate groups of the N-substituted O-substituted thiocarbamate being in the range of 1 to 100; to a composition for transporting and storing a compound with a thioureido group that includes a compound with a thioureido group and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the thioureido groups of the compound with a thioureido group being in the range of 1 to 100; and to an isothiocyanate composition containing an isothiocyanate and a compound with a specific functional group.

  该发明涉及一种使用有机初级胺和硫脲作为起始原料的异硫氰酸酯生产方法；一种用于运输和储存N-取代O-取代硫代氨基甲酸酯的组合物，包括N-取代O-取代硫代氨基甲酸酯和羟基化合物，羟基化合物的羟基与N-取代O-取代硫代氨基甲酸酯的羰基的当量重量比在1到100的范围内；一种用于运输和储存具有硫脲基团的化合物的组合物，包括具有硫脲基团的化合物和羟基化合物，羟基化合物的羟基与具有硫脲基团的化合物的硫脲基团的当量重量比在1到100的范围内；以及含有异硫氰酸酯和具有特定功能基团的化合物的异硫氰酸酯组合物。
• A New and Facile Route for the Synthesis of Thiocarbamates from Aniline, Carbon Monoxide, and Thiols Mediated by Selenium
  作者：Xiaopeng Zhang、Shiwei Lu

  DOI：10.1246/cl.2005.606

  日期：2005.4

  A new and facile route for the synthesis of thiocarbamates was reported. Mediated by selenium, aniline reacts very readily with carbon monoxide and thiols in the presence of triethylamine, to afford the corresponding thiocarbamates mostly in moderate to excellent yields under mild reaction conditions. Selenium can be easily recovered and recycled.

  报道了合成硫代氨基甲酸酯的一种新的简便途径。在硒的介导下，苯胺在三乙胺的存在下非常容易与一氧化碳和硫醇反应，在温和的反应条件下以中等至极好的收率提供相应的硫代氨基甲酸酯。硒可以很容易地回收和再循环。
• One‐Pot Direct Synthesis of Thiocarbamates from Aniline, Carbon Monoxide, and Thiols Catalyzed by Selenium
  作者：Xiaopeng Zhang、Shiwei Lu

  DOI：10.1080/00397910701483506

  日期：2007.9.1

  Abstract Catalyzed by selenium, oxidative carbonylation of aniline and thiols with carbon monoxide and oxygen affords the corresponding thiocarbamates mostly in moderate to good yields under solvent‐free conditions at ambient temperature.

  摘要 在硒的催化下，苯胺和硫醇与一氧化碳和氧气的氧化羰基化在室温无溶剂条件下以中等至良好的产率获得相应的硫代氨基甲酸酯。