O-isobutyl phenylthiocarbamate | 27830-90-6

• 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: O-isobutyl phenylthiocarbamate
• 英文别名: phenyl-thiocarbamic acid O-isobutyl ester；Phenyl-thiocarbamidsaeure-O-isobutylester；Thiocarbanilsaeure-O-isobutylester；1-(2-methylpropoxy)-N-phenylmethanimidothioic acid
• CAS: 27830-90-6
• 化学式: C₁₁H₁₅NOS
• 分子量: 209.312
• InChiKey: ZWNZTWZQIHCOAM-UHFFFAOYSA-N

物化性质

• 熔点：
  75 °C
• 沸点：
  276.0±23.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-isobutyl phenylthiocarbamate 、 甲烷磺酰基叠氮化物 以 水 为溶剂， 反应 24.0h， 以54%的产率得到isobutyl N′-methanesulfonyl-N-phenylcarbamimidate
  参考文献：
  名称：

  通过磺化点击反应合成磺酰脲类

  摘要：

  据报道，通过硫代点击反应的新变体，由硫代氨基甲酸酯和磺酰叠氮化物合成了磺酰脲类。已发现，与测试的其他各种溶剂相比，水是一种对环境无害的选择，并且不需要使用任何添加剂即可获得完全的转化率。实验上简单的反应可耐受连接在硫代氨基甲酸酯和磺酰叠氮化物上的广泛的供电子和吸电子取代基，如27种磺酰脲类的合成所示，其收率范围为34％至78％。

  DOI：

  10.1055/s-0039-1691505
• 作为产物：
  描述：

  bis-isobutoxythiocarbonyl-disulfane 、 苯胺 在 乙醚 作用下， 生成 O-isobutyl phenylthiocarbamate
  参考文献：
  名称：

  Mylius, Chemische Berichte, 1872, vol. 5, p. 978

  摘要：

  DOI：

文献信息

• Effect of successive increase in alcohol chains on reaction with isocyanates and isothiocyanates
  作者：Shahnaz Perveen、Arfa Yasmin、Khalid Mohammed Khan

  DOI：10.1080/14786410802270738

  日期：2010.1.10

  The reaction of isocyanates and isothiocyanates with long-chain alcohols, e.g. n-hexanol, n-heptanol and n-octanol, exclusively gave N-aryl-O-alkyl carbamates, while N-aryl-O-alkyl carbamates were formed along with symmetrical 1,3-disubstituted ureas and thioureas when the same reactions were carried out with small-chain alcohols at room temperature without using any solvent.

  异氰酸酯和异硫氰酸酯与长链醇，例如将反应Ñ己醇，Ñ庚醇和Ñ辛醇，只给Ñ -芳基- ø -烷基氨基甲酸盐，而Ñ -芳基- ö烷基用对称沿形成氨基甲酸酯当在不使用任何溶剂的情况下与小链醇在室温下进行相同的反应时，1,3-二取代的脲和硫脲。
• Csueroes; Rusznak, 1944, vol. 50, p. 66,77
  作者：Csueroes、Rusznak

  DOI：——

  日期：——
• Wheeler; Barnes, American Chemical Journal, 1900, vol. 24, p. 76
  作者：Wheeler、Barnes

  DOI：——

  日期：——
• Orndorff; Richmond, American Chemical Journal, 1899, vol. 22, p. 470,471, 472
  作者：Orndorff、Richmond

  DOI：——

  日期：——
• Synthesis of N-(3- and 4-substituted phenyl)-O-isobutyl thionocarbamates from O-isobutyl xanthate and amines using a nano-platinum multi-walled carbon nanotube catalyst
  作者：Milutin M. Milosavljević、Goran D. Vuković、Aleksandar D. Marinković、Radoslav Aleksić、Petar S. Uskoković

  DOI：10.1007/s00706-011-0568-5

  日期：2011.10

  Twelve N-(3- and 4-substituted phenyl)-O-isobutyl thionocarbamates, eight of which are novel, were synthesized from O-isobutyl xanthate and 3- and 4-substituted anilines in the presence of a nano-platinum aminophenyl modified multi-walled carbon nanotube catalyst. The nano-Pt catalyst was prepared on a carbon nanotube support modified by diazotization, nitro group reduction, and subsequent microwave-assisted nano-Pt precipitation. The catalyst was characterized by Fourier transform infrared (FT-IR) spectroscopy, elemental analysis, thermogravimetric analysis, and transmission electron microscopy. The nano-platinum/modified carbon nanotube catalyst was compared with a commercial Pt/active carbon catalyst in terms of product purity and yield. The results obtained by the use of the catalysts were additionally compared with those obtained by reaction of sodium isobutyl xanthogenacetate and 3- and 4-substituted anilines. Full structure characterization of the synthesized N-(substituted phenyl)-O-isobutyl thionocarbamates was achieved using FT-IR, H-1 and C-13 NMR, and mass spectrometric methods, and their purity was proved by elemental analysis and gas chromatography. The new catalytic method offers advantages over the commercial method, such as higher yields and no product purification is required, thus conforming to the principles of ecologically friendly syntheses.