2-(2-isocyanophenyl)naphthalene | 66252-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-isocyanophenyl)naphthalene
• 英文别名: 2-(2-Isocyanophenyl)naphthalene
• CAS: 66252-10-6
• 化学式: C₁₇H₁₁N
• 分子量: 229.281
• InChiKey: LBWGJYOOEBWFAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-isocyanophenyl)naphthalene 在 disodium hydrogenphosphate 、 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 5-(difluoromethyl)benzo[i]phenanthridine
  参考文献：
  名称：

  Visible-Light-Mediated Fluoroalkylation of Isocyanides with Ethyl Bromofluoroacetates: Unified Synthesis of Mono- and Difluoromethylated Phenanthridine Derivatives

  摘要：

  A practical and unified strategy has been described for the preparation of mono- and difluoromethylated phenanthridine derivatives using a visible-light-promoted alkylation and decarboxylation sequence from biphenyl isocyanides with ethyl bromofluoroacetate (EBFA) or ethyl bromodifluoroacetate (EBDFA). These reactions could be carried out at room temperature in good to excellent chemical yields. Both stepwise and one-pot procedures have been developed, which makes this strategy more attractive.

  DOI：

  10.1021/ol501081h
• 作为产物：
  描述：

  2-溴苯胺 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 4.5h， 生成 2-(2-isocyanophenyl)naphthalene
  参考文献：
  名称：

  银催化自由基级联芳硫基二氟甲基化/异腈环化用于合成 6-菲啶基二氟甲基芳基硫醚

  摘要：

  研究了在银催化条件下通过芳硫基二氟乙酸盐氧化脱羧工艺合成6-菲啶基二氟甲基芳基硫醚的自由基异腈插入级联反应。

  DOI：

  10.1002/asia.202200088

文献信息

• Silver‐Enabled General Radical Difluoromethylation Reaction with TMSCF ₂ H
  作者：Jun Yang、Shengqing Zhu、Fang Wang、Feng‐Ling Qing、Lingling Chu

  DOI：10.1002/anie.202014587

  日期：2021.2.19

  A silver‐mediated oxidative difluoromethylation of styrenes and vinyl trifluoroborates with TMSCF2H is reported for the first time. This method enables direct and facile access to CF2H‐alkenes from abundant alkenes with excellent functional‐group compatibility. Moreover, this Ag/TMSCF2H protocol could further enable a series of radical difluoromethylation reactions of a wide array of substrates, offering

  首次报道了用TMSCF 2 H对苯乙烯和三氟硼酸乙烯基酯进行银介导的氧化二氟甲基化。这种方法可以从丰富的烯烃中直接和轻松地获得CF 2 H-烯烃，并且具有出色的官能团相容性。此外，该Ag / TMSCF 2 H方案可以进一步实现一系列底物的一系列自由基二氟甲基化反应，从而为构建多样化的C-CF 2 H键提供通用和互补的平台。
• Synthesis of 6-aroyl phenanthridines by Fe-catalyzed oxidative radical cyclization of 2-isocyanobiphenyls with benzylic alcohols
  作者：Ziyi Nie、Qiuping Ding、Yiyuan Peng

  DOI：10.1016/j.tet.2016.11.010

  日期：2016.12

  A practical method for the synthesis of 6-aroyl phenanthridine derivatives by Fe-catalyzed oxidative radical cyclization of 2-isocyanobiphenyls with benzylic alcohols is described. In addition, this cyclization could be occurred by using toluene as aroyl source. The procedure tolerates various functional groups under simple conditions. A single-electron-transfer pathway is proposed according to mechanistic

  描述了一种通过Fe催化的2-异氰基联苯与苯甲醇的氧化自由基环化合成6-芳基菲啶衍生物的实用方法。另外，可以通过使用甲苯作为芳酰基源来发生这种环化。该程序可以在简单条件下容忍各种官能团。根据机理研究提出了单电子转移途径。
• Selective C(sp³)–H activation of simple alkanes: visible light-induced metal-free synthesis of phenanthridines with H₂O₂ as a sustainable oxidant
  作者：Yongqiang Zhang、Yunhe Jin、Lifang Wang、Qingqing Zhang、Changgong Meng、Chunying Duan

  DOI：10.1039/d1gc02670d

  日期：——

  A visible light-induced metal-free C(sp³)–H phenanthridinylation of simple alkanes with isonitrile is developed with H₂O₂ as a terminal sustainable oxidant.

  一种可见光诱导的金属催化剂自由的简单烷烃与异腈的C(sp3)-H菲啰啉化反应被开发，其中H2O2作为终端可持续氧化剂。
• Transition-metal-free, visible-light induced cyclization of arylsulfonyl chlorides with 2-isocyanobiphenyls to produce phenanthridines
  作者：Lijun Gu、Cheng Jin、Jiyan Liu、Hongyan Ding、Baomin Fan

  DOI：10.1039/c4cc01487a

  日期：——

  A visible-light promoted transformation of 2-isocyanobiphenyls and arylsulfonyl chlorides for the synthesis of phenanthridines under oxidant-free and transition-metal-free conditions was described.

  2-异氰基联苯和芳基磺酰氯在无氧化剂和过渡金属的条件下，经可见光促进转化合成菲啰啉。
• 6-Aroylated Phenanthridines via Base Promoted Homolytic Aromatic Substitution (BHAS)
  作者：Dirk Leifert、Constantin Gabriel Daniliuc、Armido Studer

  DOI：10.1021/ol403147v

  日期：2013.12.20

  2-isocyanobiphenyls react with aromatic aldehydes via base promoted homolytic aromatic substitution (BHAS) to give 6-aroylated phenanthridines. Reactions occur via addition of acyl radicals to the isonitrile functionality and subsequent intramolecular BHAS of the intermediate imidoyl radicals. Initiation of the radical chain reaction is best achieved with small amounts of FeCl3 (0.4 mol %), and the commercially

  易于获得的2-异氰基联苯通过碱促进的均相芳族取代（BHAS）与芳族醛反应，生成6-芳基化菲啶。反应是通过将酰基基团加到异腈官能团上，以及随后的中间体亚氨基基团的分子内BHAS发生的。自由基链反应的引发最好用少量的FeCl 3（0.4 mol％）来实现，并且使用市售的廉价t BuOOH作为氧化剂。