methyl (2-phenylthioethyl)carbamate | 91012-35-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl (2-phenylthioethyl)carbamate
• 英文别名: N-2-Phenylmercapto-aethylcarbamidsaeure-methylester；N-2-Phenylthioethyl-O-methylcarbamat；methyl N-(2-phenylsulfanylethyl)carbamate
• CAS: 91012-35-0
• 化学式: C₁₀H₁₃NO₂S
• mdl: MFCD24389377
• 分子量: 211.285
• InChiKey: NBSJALYHKQFDTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 5-amino-3-[(2,4-dimethoxyphenyl)methyl]imidazole-4-carboxylate 、 methyl (2-phenylthioethyl)carbamate 在 potassium tert-butylate 作用下， 以 二乙二醇二甲醚 为溶剂， 以58%的产率得到7-(2,4-dimethoxybenzyl)-1-(2-phenylthioethyl)-3,7-dihydropurine-2,6-dione
  参考文献：
  名称：

  Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy

  摘要：

  An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.067
• 作为产物：
  描述：

  甲醇 、 aziridine-1-carbothioic acid S-phenyl ester 在 sodium iodide 作用下， 生成 methyl (2-phenylthioethyl)carbamate
  参考文献：
  名称：

  Mechanism of the isomerization of 1-(arylthiocarbonyl)aziridines to 2-(arylthioalkyl)isocyanates

  摘要：

  DOI：

  10.1021/jo00826a012

文献信息

• Mechanism of the isomerization of 1-(arylthiocarbonyl)aziridines to 2-(arylthioalkyl)isocyanates
  作者：Donald A. Tomalia、David P. Sheetz、G. E. Ham

  DOI：10.1021/jo00826a012

  日期：1970.1.1
• Efficient synthesis of 1,3,7-substituted xanthines by a safety-catch protection strategy
  作者：Matthew B. Allwood、Booma Cannan、Daan M.F. van Aalten、Ian M. Eggleston

  DOI：10.1016/j.tet.2007.09.067

  日期：2007.12

  An efficient synthesis of selectively N-substituted xanthine derivatives is described. Cyclocondensation of a suitably protected ammoimidazole with methyl-2-phenylthioethyl carbamate, followed by oxidation of sulfur to the sulfone, provides access to an orthogonally 1,7-protected xanthine, which may then be regioselectively alkylated and deprotected under mild conditions. (c) 2007 Elsevier Ltd. All rights reserved.