1-(2-(4-methoxybenzylthio)acetyl)-2-methyl-3-phenylisothiourea | 1011290-96-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-(4-methoxybenzylthio)acetyl)-2-methyl-3-phenylisothiourea
• 英文别名: methyl N-[2-[(4-methoxyphenyl)methylsulfanyl]acetyl]-N'-phenylcarbamimidothioate
• CAS: 1011290-96-2
• 化学式: C₁₈H₂₀N₂O₂S₂
• 分子量: 360.501
• InChiKey: JUCREFYLEXHZOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-(4-methoxybenzylthio)acetyl)-2-methyl-3-phenylisothiourea 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以77%的产率得到2-苯氨基噻唑-4-酮
  参考文献：
  名称：

  New Methods for the Synthesis of 2-Aminothiazolones

  摘要：

  [GRAPHICS]Two new methods for the synthesis of 2-aminothiazolones from 2-(4-methoxybenzylthio)acetic acids are described. A single reagent and simple experimental conditions are used in the key tandem deprotection-cyclization process. In the first approach 2-aminothiazolones are directly accessed via cyclization of the corresponding N-acylisothioureas. The second complementary approach provides access to a variety of 2-thiomethylthiazoiones via cyclization of N-acyldithioimidates. The product 2-thiomethylthiazol ones are then efficiently converted to 2-aminothiazolones via amine displacement.

  DOI：

  10.1021/jo702369f
• 作为产物：
  描述：

  (4-methoxy-benzylsulfanyl)-acetic acid 、 S-methyl-N-phenylisothiourea hydroiodide 在 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以84%的产率得到1-(2-(4-methoxybenzylthio)acetyl)-2-methyl-3-phenylisothiourea
  参考文献：
  名称：

  New Methods for the Synthesis of 2-Aminothiazolones

  摘要：

  [GRAPHICS]Two new methods for the synthesis of 2-aminothiazolones from 2-(4-methoxybenzylthio)acetic acids are described. A single reagent and simple experimental conditions are used in the key tandem deprotection-cyclization process. In the first approach 2-aminothiazolones are directly accessed via cyclization of the corresponding N-acylisothioureas. The second complementary approach provides access to a variety of 2-thiomethylthiazoiones via cyclization of N-acyldithioimidates. The product 2-thiomethylthiazol ones are then efficiently converted to 2-aminothiazolones via amine displacement.

  DOI：

  10.1021/jo702369f

文献信息

• New Methods for the Synthesis of 2-Aminothiazolones
  作者：Seb Caille、Eric A. Bercot、Sheng Cui、Margaret M. Faul

  DOI：10.1021/jo702369f

  日期：2008.3.1

  [GRAPHICS]Two new methods for the synthesis of 2-aminothiazolones from 2-(4-methoxybenzylthio)acetic acids are described. A single reagent and simple experimental conditions are used in the key tandem deprotection-cyclization process. In the first approach 2-aminothiazolones are directly accessed via cyclization of the corresponding N-acylisothioureas. The second complementary approach provides access to a variety of 2-thiomethylthiazoiones via cyclization of N-acyldithioimidates. The product 2-thiomethylthiazol ones are then efficiently converted to 2-aminothiazolones via amine displacement.