| 1609487-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1609487-04-8
• 化学式: C₁₄H₈F₃NO
• 分子量: 263.219
• InChiKey: JTGJMTKSYAVWOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  13.59
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  肼基甲酸甲酯 、 在 叔丁基过氧化氢 、 iron(II) diacetylacetonate 作用下， 以 氟苯 、 水 为溶剂， 反应 12.0h， 以67%的产率得到methyl 2-(trifluoromethoxy)phenanthridine-6-carboxylate
  参考文献：
  名称：

  Radical Arylalkoxycarbonylation of 2-Isocyanobiphenyl with Carbazates: Dual C–C Bond Formation toward Phenanthridine-6-carboxylates

  摘要：

  A sequential oxidative radical alkoxycarbonylation and aromatization of 2-isocyanobiphenyl with carbazates was developed to furnish phenanthridine-6-carboxylates. Various functional groups such as methoxy, chloro, fluoro, trifluoromethoxy, and trifluoromethyl groups were tolerated well under the reaction conditions. The sequential radical addition-cyclization strategy represents a practical route to access phenanthridine-6-carboxylates.

  DOI：

  10.1021/jo500842e

文献信息

• A radical addition/cyclization of diverse ethers to 2-isocyanobiaryls under mildly basic aqueous conditions
  作者：Cintia Anton-Torrecillas、Diego Felipe-Blanco、Jose C. Gonzalez-Gomez

  DOI：10.1039/c6ob02103d

  日期：——

  Mildly basic aqueous conditions facilitated the tert-butyl peroxybenzoate (TBPB) mediated dehydrogenative addition of a range of ethers, including acetals, to diverse substituted 2-isocyanobiaryls. Mechanistic studies suggest that this radical cascade is an example of base promoted homolytic aromatic substitution (BHAS).

  温和的碱性水性条件促进了过氧苯甲酸叔丁酯（TBPB）介导的一系列醚（包括缩醛）的脱氢加成到各种取代的2-异氰基双芳基化合物中。机理研究表明，这种自由基级联是碱促进的均相芳族取代（BHAS）的一个例子。
• Tandem dual C(sp3)-H/C(sp2)-H functionalization: a radical cyclization of 2-isocyanobiphenyl with ether to 6-alkylated phenanthridine
  作者：ChangDuo Pan、Jie Han、Zhu ChengJian

  DOI：10.1007/s11426-014-5118-7

  日期：2014.8

  A simple and efficient radical coupling of 2-isocyanobiphenyl with ethers was developed, providing a variety of 6-alkylated phenanthridines. Both cyclic and acyclic ethers are suitable substrates for this transformation, which comprised the functionalization of two C-H bonds: the sp3 C-H of ether and sp2 C-H of phenyl group. The kinetic isotope effect (KIE) revealed that the cleavage of sp3 C-H bond would be involved in the rate-determining step.

  开发了一种简单高效的2-异氰基联苯与醚的偶联反应，生成多种6-烷基化的吩噻嗪。环状和非环状醚均可作为该反应的底物，涉及两个C-H键的功能化：醚的sp3 C-H键和苯基的sp2 C-H键。动力学同位素效应（KIE）表明，sp3 C-H键的断裂是决速步。
• Metal-free radical oxidative decarboxylation/cyclization of acyl peroxides and 2-isocyanobiphenyls
  作者：Changduo Pan、Honglin Zhang、Jie Han、Yixiang Cheng、Chengjian Zhu

  DOI：10.1039/c4cc10015h

  日期：——

  A metal-free radical oxidative decarboxylation/cyclization of acyl peroxides and 2-isocyanobiphenyls was achieved, leading to 6-aryl phenanthridines as well as 6-alkyl phenanthridines in moderate to good yields. The procedure featured simple conditions and was metal-free and base free. It represents a practical approach to access 6-aryl/alkyl phenanthridines.

  实现了酰基过氧化物和2-异氰基联苯的金属自由基氧化脱羧/环化反应，从而以中等至良好的收率得到了6-芳基菲啶和6-烷基菲啶。该过程条件简单，不含金属和碱。它代表了一种接近6-芳基/烷基菲啶的实用方法。