(2-chlorophenylcarbamoyl)methyl diacetate | 97965-89-4

• 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: (2-chlorophenylcarbamoyl)methyl diacetate
• 英文别名: [1-acetyloxy-2-(2-chloroanilino)-2-oxoethyl] acetate
• CAS: 97965-89-4
• 化学式: C₁₂H₁₂ClNO₅
• 分子量: 285.684
• InChiKey: YCBFNYXSBOPPLH-UHFFFAOYSA-N

物化性质

• 沸点：
  472.6±45.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2-chlorophenylcarbamoyl)methyl diacetate 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 N-(2-chlorophenyl)-2-isonitrosoacetanilide
  参考文献：
  名称：

  An improved synthesis of isonitrosoacetanilides

  摘要：

  A novel two-step synthesis of isonitrosoacetanilides [2-(hydroxyimino)-N-phenylacetamides] has been developed, involving the initial acylation of aniline derivatives with 2,2-diacetoxyacetyl chloride, followed by reaction with hydroxylamine hydrochloride. The method works equally well with a variety of different aniline derivatives, including those with poor aqueous solubility and those containing electron rich ortho-substituents, neither of which react well under traditional conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.046
• 作为产物：
  描述：

  2,2-二乙酰氧基乙酸 在 氯化亚砜 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2-chlorophenylcarbamoyl)methyl diacetate
  参考文献：
  名称：

  An improved synthesis of isonitrosoacetanilides

  摘要：

  A novel two-step synthesis of isonitrosoacetanilides [2-(hydroxyimino)-N-phenylacetamides] has been developed, involving the initial acylation of aniline derivatives with 2,2-diacetoxyacetyl chloride, followed by reaction with hydroxylamine hydrochloride. The method works equally well with a variety of different aniline derivatives, including those with poor aqueous solubility and those containing electron rich ortho-substituents, neither of which react well under traditional conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.046

文献信息

• Iodobenzene Diacetate (PIDA)/Zn(II)-Mediated Oxidation and Cleavage of C–C Bond: Formation of Substituted N-aryl Carbamoyl Methyl Diacetates and Derivatives from 3-oxo-butanamides
  作者：Hu Wenjun、Deng Zhaohui、Cui Chen、Wei-Bing Liu

  DOI：10.3184/174751912x13445852334047

  日期：2012.10

  Various substituted N-aryl carbamoyl methyl diacetates have been synthesized from N-aryl-3-oxobutanamides via a diacetoxylation mediated by the combination of iodobenzene diacetate (PIDA)/Zn(OAc)2. This provides a new convenient method to form C–O bonds and cleave C–C bonds. Ten examples were obtained from easily available materials in good to excellent yields.

  已经从 N-芳基-3-氧代丁酰胺通过碘苯二乙酸酯 (PIDA)/Zn(OAc)2 的组合介导的二乙酰氧基化合成了各种取代的 N-芳基氨基甲酰基二乙酸甲酯。这为形成 C-O 键和裂解 C-C 键提供了一种新的便捷方法。十个例子是从容易获得的材料中获得的，产率很好。