tert-butyl 6-oxophenanthridine-5(6H)-carboxylate | 1103883-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl 6-oxophenanthridine-5(6H)-carboxylate
• 英文别名: 5-tert-butyloxycarbonylphenanthridin-6(5H)-one；Tert-butyl 6-oxophenanthridine-5-carboxylate；tert-butyl 6-oxophenanthridine-5-carboxylate
• CAS: 1103883-20-0
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: WGDUVTJWUVQJNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl phenanthridine-5(6H)-carboxylate 在 sodium chlorite 作用下， 以 三氯乙烷 、 水 为溶剂， 反应 6.0h， 以84%的产率得到tert-butyl 6-oxophenanthridine-5(6H)-carboxylate
  参考文献：
  名称：

  A Simple and Effective Synthesis of Benzolactones and Benzolactams by Noncatalytic­ Benzylic Oxidation of Cyclic Benzylic Ethers and N-Protected Cyclic Benzylic Amines with Sodium Chlorite as an Oxidant

  摘要：

  Sodium chlorite (NaClO2) was shown to be capable of oxidizing cyclic benzylic ethers and N-protected cyclic benzylic amines in a heterogeneous solvent system of 1,1,1-trichloroethane and water at 55-65 degrees C to give synthetically useful benzolactones and benzolactams, respectively, in high-to-excellent yields.

  DOI：

  10.1055/s-0032-1316747

文献信息

• Radical 1,4-aryl transfer in arylcarboxamides leading to phthalimides, biaryls and enantiomerically enriched β-arylethylamines
  作者：Jeremy Robertson、Matthew J. Palframan、Stephen A. Shea、Kirill Tchabanenko、William P. Unsworth、Chase Winters

  DOI：10.1016/j.tet.2008.07.118

  日期：2008.12

  5-exo Cyclisation of vinyl-, aryl- and alkyl-radicals onto the aryl group of arylcarboxamides is followed by beta-scission of the resulting spirocyclohexadienyl radicals with ejection of a carbamoyl radical. The fate of this radical depends on the substrate but, in the cases studied, either 5-endo cyclisation or direct reduction follows to give phthalimides, biaryls or beta-arylethylamines. (C) 2008 Elsevier Ltd. All rights reserved.