methyl [2-(iodoacetyl)phenyl]carbamate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl [2-(iodoacetyl)phenyl]carbamate
• 英文别名: Methyl [(iodoacetyl)phenyl]carbamate；methyl N-[2-(2-iodoacetyl)phenyl]carbamate
• 化学式: C₁₀H₁₀INO₃
• 分子量: 319.099
• InChiKey: JLWMRFBACQGDCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl [2-(iodoacetyl)phenyl]carbamate 、 2-氨基-2-苯基乙酸 在 碘 、 二甲基亚砜 、 对氨基苯磺酸 作用下， 反应 5.0h， 以76%的产率得到methyl [2-(2-phenyl-1,3-oxazol-5-yl)phenyl]carbamate
  参考文献：
  名称：

  Synthesis of 2,5-diaryl-1,3-oxazoles containing a carbamate group

  摘要：

  Acetophenones containing a methoxycarbonylamino group in position 2, 3, or 4 of the aromatic ring reacted with phenylglycine in the presence of 2 equiv of iodine and 0.5 equiv of sulfanilic acid in DMSO at 100 degrees C for 6 h to give methyl [2(3,4)-(2-phenyl-1,3-oxazol-5-yl)phenyl]carbamates. The reaction was presumed to involve intermediate formation of methyl [(iodoacetyl)phenyl]carbamate. This was confirmed by the isolation of methyl [2-(iodoacetyl) phenyl]carbamate in the reaction of methyl (2-acetylphenyl)carbamate with iodine in glacial acetic acid and its subsequent transformation to methyl [2-(2-phenyl-1,3-oxazol-5-yl)phenyl]carbamate.

  DOI：

  10.1134/s1070428017120120
• 作为产物：
  描述：

  methyl (2-acetylphenyl)carbamate 在 碘 、 溶剂黄146 作用下， 反应 7.0h， 以75%的产率得到methyl [2-(iodoacetyl)phenyl]carbamate
  参考文献：
  名称：

  Synthesis of 2,5-diaryl-1,3-oxazoles containing a carbamate group

  摘要：

  Acetophenones containing a methoxycarbonylamino group in position 2, 3, or 4 of the aromatic ring reacted with phenylglycine in the presence of 2 equiv of iodine and 0.5 equiv of sulfanilic acid in DMSO at 100 degrees C for 6 h to give methyl [2(3,4)-(2-phenyl-1,3-oxazol-5-yl)phenyl]carbamates. The reaction was presumed to involve intermediate formation of methyl [(iodoacetyl)phenyl]carbamate. This was confirmed by the isolation of methyl [2-(iodoacetyl) phenyl]carbamate in the reaction of methyl (2-acetylphenyl)carbamate with iodine in glacial acetic acid and its subsequent transformation to methyl [2-(2-phenyl-1,3-oxazol-5-yl)phenyl]carbamate.

  DOI：

  10.1134/s1070428017120120