N'-hydroxy-N-methyl-N-phenylurea | 13262-41-4

• 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'-hydroxy-N-methyl-N-phenylurea
• 英文别名: 3-Hydroxy-1-methyl-1-phenylurea
• CAS: 13262-41-4
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: UDJKPENTLREIMW-UHFFFAOYSA-N

物化性质

• 熔点：
  105-110 °C
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N'-hydroxy-N-methyl-N-phenylurea 在 iron(II) triflate 、 2,2'-联吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 10.0h， 生成 1-甲基-2-苯咪唑啉酮
  参考文献：
  名称：

  铁催化的N-苯甲酰氧基脲分子内CH-酰胺化反应

  摘要：

  描述了N-苯甲酰氧基脲的氧化还原中性铁催化的分子内CH酰胺化。该方法采用的是由Fe（OTf）2和联吡啶作为催化剂而原位生成的简单铁络合物，而作为氮烯前体的N-苯甲酰氧基脲则不使用外源氧化剂。通过脂族C（sp 3）-H酰胺化以优异的产率合成了一系列环状脲。另外，该催化体系也适合芳基C（sp 2）-H亚硝基插入，以中等产率提供苯并咪唑酮。

  DOI：

  10.1002/cjoc.202100005
• 作为产物：
  描述：

  N-甲基-N-苯基氨基甲酰氯 在 盐酸羟胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以15%的产率得到N'-hydroxy-N-methyl-N-phenylurea
  参考文献：
  名称：

  Analogues of N-hydroxy-N′-phenylthiourea and N-hydroxy-N′-phenylurea as inhibitors of tyrosinase and melanin formation

  摘要：

  A series of N-hydroxy-N'-phenylthiourea and N-hydroxy-N'-phenylurea analogues were prepared and evaluated as inhibitors of tyrosinase and melanin formation. The most active analogue 1 inhibited mushroom tyrosinase with an IC(50) of around 0.29 mu M and also retained a substantial potency in cell culture by reducing pigment synthesis by 78%. Therefore, compound 1 could be considered as a promising candidate for preclinical drug development for skin hyperpigmentation application. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.079

文献信息

• 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.
• <scp>Iron‐Catalyzed</scp> Intramolecular C—H Amidation of <scp> <i>N</i> ‐Benzoyloxyureas </scp>
  作者：Dayou Zhong、Lin‐Yang Wu、Xing‐Zhen Wang、Wen‐Bo Liu

  DOI：10.1002/cjoc.202100005

  日期：2021.4

  A redox‐neutral Fe‐catalyzed intramolecular C—H amidation of N‐benzoyloxyureas is described. This methodology employs a simple iron complex in situ generated from Fe(OTf)2 and bipyridine as the catalyst and N‐benzoyloxyureas as the nitrene precursors without using exogenous oxidants. An array of cyclic ureas were synthesized via aliphatic C(sp3)—H amidation in excellent yields. In addition, this catalytic

  描述了N-苯甲酰氧基脲的氧化还原中性铁催化的分子内CH酰胺化。该方法采用的是由Fe（OTf）2和联吡啶作为催化剂而原位生成的简单铁络合物，而作为氮烯前体的N-苯甲酰氧基脲则不使用外源氧化剂。通过脂族C（sp 3）-H酰胺化以优异的产率合成了一系列环状脲。另外，该催化体系也适合芳基C（sp 2）-H亚硝基插入，以中等产率提供苯并咪唑酮。
• Analogues of N-hydroxy-N′-phenylthiourea and N-hydroxy-N′-phenylurea as inhibitors of tyrosinase and melanin formation
  作者：Marc Criton、Véronique Le Mellay-Hamon

  DOI：10.1016/j.bmcl.2008.04.079

  日期：2008.6

  A series of N-hydroxy-N'-phenylthiourea and N-hydroxy-N'-phenylurea analogues were prepared and evaluated as inhibitors of tyrosinase and melanin formation. The most active analogue 1 inhibited mushroom tyrosinase with an IC(50) of around 0.29 mu M and also retained a substantial potency in cell culture by reducing pigment synthesis by 78%. Therefore, compound 1 could be considered as a promising candidate for preclinical drug development for skin hyperpigmentation application. (C) 2008 Elsevier Ltd. All rights reserved.