2-(4-Methylphenyl)-2-oxoethyl 3-chlorobenzoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-Methylphenyl)-2-oxoethyl 3-chlorobenzoate
• 英文别名: [2-(4-methylphenyl)-2-oxoethyl] 3-chlorobenzoate
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: SMMZYESRIIDIOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(1-azidovinyl)-4-methylbenzene 在 N-溴代丁二酰亚胺(NBS) 、 silver(I) nitrite 、 水 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 2-(4-Methylphenyl)-2-oxoethyl 3-chlorobenzoate
  参考文献：
  名称：

  Radical Enamination of Vinyl Azides: Direct Synthesis of N-Unprotected Enamines

  摘要：

  An electron-withdrawing-group-generable radical-induced enamination of vinyl azides is reported, which results in a variety of beta-functionalized N-unprotected enamines in a stereoselective manner. A plausible mechanism involving an unusual 1,3-H transfer of in situ generated iminyl radical intermediate was proposed on the basis of experimental results and DFT calculations.

  DOI：

  10.1021/acs.orglett.7b03204

文献信息

• Radical Enamination of Vinyl Azides: Direct Synthesis of <i>N</i>-Unprotected Enamines
  作者：Yongquan Ning、Xue-Feng Zhao、Yan-Bo Wu、Xihe Bi

  DOI：10.1021/acs.orglett.7b03204

  日期：2017.11.17

  An electron-withdrawing-group-generable radical-induced enamination of vinyl azides is reported, which results in a variety of beta-functionalized N-unprotected enamines in a stereoselective manner. A plausible mechanism involving an unusual 1,3-H transfer of in situ generated iminyl radical intermediate was proposed on the basis of experimental results and DFT calculations.