1-(1-hydroxy-3-methylbutan-2-yl)-3-phenylthiourea | 254900-23-7

• 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: 1-(1-hydroxy-3-methylbutan-2-yl)-3-phenylthiourea
• 英文别名: 1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-3-phenylthiourea
• CAS: 254900-23-7
• 化学式: C₁₂H₁₈N₂OS
• 分子量: 238.354
• InChiKey: RTUJKZXZUIRBIF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-hydroxy-3-methylbutan-2-yl)-3-phenylthiourea 在 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 N-phenyl-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-amine
  参考文献：
  名称：

  A Selective and Convenient Method for the Synthesis of 2-Phenylaminothiazolines

  摘要：

  A series of 2-phenylaminothiazolines have been prepared from the corresponding N-(2-hydroxyethyl)-N'-phenylthioureas under mild reaction conditions using either thio-CDI (1,1'-thiocarbonyldiimidazole) or CDI (1,1'-carbonyldiimidazole) to promote the cyclization. This protocol provides the desired cyclization products in good yield with excellent selectivity. The scope and selectivity of this methodology are also described.

  DOI：

  10.1021/ol102428m
• 作为产物：
  描述：

  L-缬氨醇 、 硫代异氰酸苯酯 以 四氢呋喃 为溶剂， 以93%的产率得到1-(1-hydroxy-3-methylbutan-2-yl)-3-phenylthiourea
  参考文献：
  名称：

  A Selective and Convenient Method for the Synthesis of 2-Phenylaminothiazolines

  摘要：

  A series of 2-phenylaminothiazolines have been prepared from the corresponding N-(2-hydroxyethyl)-N'-phenylthioureas under mild reaction conditions using either thio-CDI (1,1'-thiocarbonyldiimidazole) or CDI (1,1'-carbonyldiimidazole) to promote the cyclization. This protocol provides the desired cyclization products in good yield with excellent selectivity. The scope and selectivity of this methodology are also described.

  DOI：

  10.1021/ol102428m

文献信息

• One-pot synthesis of 2-phenylaminothiazolines from N-2-hydroxyethyl)-N′-phenylthioureas
  作者：Taek Hyeon Kim、Jung Ki Min、Gue-Jae Lee

  DOI：10.1016/s0040-4039(99)01704-9

  日期：1999.11

  2-Phenylaminothiazolines 3 were synthesized from N-(2-hydroxyethyl)-N'-phenylthioureas 2 by a one-pot reaction using p-toluenesulfonyl chloride (TsCl) and NaOH or Et3N. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A mild cyclodesulfurization of N-(2-hydroxyethyl)-N′-phenylthioureas to 2-phenylamino-2-oxazolines using TsCl/NaOH
  作者：Taek Hyeon Kim、Namgun Lee、Gue-Jae Lee、Jae Nyoung Kim

  DOI：10.1016/s0040-4020(01)00682-2

  日期：2001.8

  An efficient synthesis of 2-phenylamino-2-oxazolines 3 via cyclodesulfurization of N-(2-hydroxyethyl)-N ' -phenylthioureas 2 by a one-pot reaction using p-toluenesulfonyl chloride (TsCl) and NaOH in very good yields is described. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A Selective and Convenient Method for the Synthesis of 2-Phenylaminothiazolines
  作者：April L. Bernacki、Lingyang Zhu、D. David Hennings

  DOI：10.1021/ol102428m

  日期：2010.12.3

  A series of 2-phenylaminothiazolines have been prepared from the corresponding N-(2-hydroxyethyl)-N'-phenylthioureas under mild reaction conditions using either thio-CDI (1,1'-thiocarbonyldiimidazole) or CDI (1,1'-carbonyldiimidazole) to promote the cyclization. This protocol provides the desired cyclization products in good yield with excellent selectivity. The scope and selectivity of this methodology are also described.