N-phenylmethyl-N'-tert-butoxyurea

• 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: N-phenylmethyl-N'-tert-butoxyurea
• 英文别名: 1-Benzyl-3-[(2-methylpropan-2-yl)oxy]urea；1-benzyl-3-[(2-methylpropan-2-yl)oxy]urea
• 化学式: C₁₂H₁₈N₂O₂
• 分子量: 222.287
• InChiKey: AUAJBZIXZVDFGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  50.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenylmethyl-N'-tert-butoxyurea 在 盐酸 作用下， 以 水 为溶剂， 反应 0.17h， 以70%的产率得到1-苄基-3-羟基脲
  参考文献：
  名称：

  Synthesis of substituted N-hydroxyureas via the in situ generation of t-butoxy isocyanate

  摘要：

  Treatment of primary and secondary amines with tert-butylmesitylenesulfonoxycarbamate and a base afforded tert-butoxyurea, which when treated with an acid ultimately yielded substituted N-hydroxy ureas. It is proposed that this proceeded via the generation of t-butoxy isocyanate in situ. This method allows for the synthesis of both mono and disubstituted N-hydroxyureas. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.002
• 作为产物：
  描述：

  N-Boc-O-2,4,6-三甲基苯磺酰羟胺 、 苄胺 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以45%的产率得到N-phenylmethyl-N'-tert-butoxyurea
  参考文献：
  名称：

  Synthesis of substituted N-hydroxyureas via the in situ generation of t-butoxy isocyanate

  摘要：

  Treatment of primary and secondary amines with tert-butylmesitylenesulfonoxycarbamate and a base afforded tert-butoxyurea, which when treated with an acid ultimately yielded substituted N-hydroxy ureas. It is proposed that this proceeded via the generation of t-butoxy isocyanate in situ. This method allows for the synthesis of both mono and disubstituted N-hydroxyureas. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.002

文献信息

• Synthesis of Hydroxamic Esters via Alkoxyaminocarbonylation of β-Dicarbonyl Compounds
  作者：Stephen Hanessian、Shawn Johnstone

  DOI：10.1021/jo990353k

  日期：1999.8.1

  N-t-Butoxycarbonyl-O-sulfonyl-substitute hydroxylamines react with soft enolates to yield O-t-butoxycarbonylamino derivatives rather than the expected Boc-protected amino acids. The reaction is limited to enolates of beta-dicarbonyl compounds. Decarboxylation of the resultant tricarbonyl compound affords malonyl alpha-alkyl O-t-butoxycarbonylamino derivatives.
• Synthesis of substituted N-hydroxyureas via the in situ generation of t-butoxy isocyanate
  作者：Josef G. Krause、Brian D. Leskiw、Michelle L. Emery、Megan E. McGahan、Mary P. McCourt、Ronny Priefer

  DOI：10.1016/j.tetlet.2010.05.002

  日期：2010.7

  Treatment of primary and secondary amines with tert-butylmesitylenesulfonoxycarbamate and a base afforded tert-butoxyurea, which when treated with an acid ultimately yielded substituted N-hydroxy ureas. It is proposed that this proceeded via the generation of t-butoxy isocyanate in situ. This method allows for the synthesis of both mono and disubstituted N-hydroxyureas. (C) 2010 Elsevier Ltd. All rights reserved.