2-phenyl-2H-benzo[g]indazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-2H-benzo[g]indazole
• 英文别名: 2-Phenylbenzo[g]indazole；2-phenylbenzo[g]indazole
• 化学式: C₁₇H₁₂N₂
• 分子量: 244.296
• InChiKey: XHGTZNGYEKXNSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenyl-2H-benzo[g]indazole 、 (1Z)-2-偶氮基-1-乙氧基-3-氧代-3-苯基-1-丙烯-1-醇 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 三氟甲磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以52%的产率得到ethyl 6-phenylbenzo[6,7]indazolo[2,3-a]quinoline-5-carboxylate
  参考文献：
  名称：

  通过Rh（III）催化的无氧化剂[4 + 2]或[5 + 1]环合2-芳基-2H-吲唑与α-重氮羰基化合物选择性合成吲哚并[2,3-a]喹啉

  摘要：

  通过Rh（III）催化的2-芳基-2 H-吲唑与α-重氮羰基化合物的无氧化剂环氧化反应选择性合成5,6-二取代和5-取代的吲唑并[2,3- a ]喹啉是报告。以2-芳基-2 H-吲唑为底物，α-重氮羰基化合物可作为C2合成子，通过Rh（III）催化[ 5,6-二取代的吲唑并[2,3- a ]喹啉] [4 +2]。另一方面，当使用2-芳基-3-甲酰基-2 H-吲唑类作为底物时，α-重氮羰基化合物转变为C1合成子，需要经历更复杂的[5 + 1]环化工艺来提供5位取代的吲哚并[2,3- a ]喹啉。

  DOI：

  10.1002/adsc.201901422
• 作为产物：
  描述：

  1,3-二苯-1H-吡唑-4-甲醛 在 三氟甲磺酸 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 为溶剂， 反应 14.0h， 生成 2-phenyl-2H-benzo[g]indazole
  参考文献：
  名称：

  Charge Migration in Dicationic Electrophiles and Its Application to the Synthesis of Aza-polycyclic Aromatic Compounds

  摘要：

  Superacid-promoted reactions of dicationic electrophiles have been studied, and the positive charge centers are found to migrate apart in a predictable manner. Using isotopic labeling the charge migration is found in one system to occur through successive deprotonation-reprotonation steps. The charge migration chemistry is the basis for new general synthetic route to aza-polycyclic aromatic compounds.

  DOI：

  10.1021/ol060125u

文献信息

• Efficient synthesis of 2-aryl-2<i>H</i>-indazoles by base-catalyzed benzyl C–H deprotonation and cyclization
  作者：Guo-Qing Jin、Wen-Xia Gao、Yun-Bing Zhou、Miao-Chang Liu、Hua-Yue Wu

  DOI：10.1039/d0cc05862a

  日期：——

  A straightforward and efficient method for the preparation of 2-aryl-2H-indazoles from ortho-alkyl substituted azoxybenzenes is presented. The reaction proceeds through base-catalyzed benzyl C–H deprotonation and cyclization to afford 2-aryl-2H-indazoles in good yields. This synthetic strategy can be applied to the construction of several fluorescent and bioactive molecules.

  提出了一种由邻烷基取代的z氧基苯制备2-芳基-2 H-吲唑的直接有效的方法。该反应通过碱催化的苄基CH脱质子化和环化反应进行，以高收率得到2-芳基-2 H-吲唑。这种合成策略可以应用于几种荧光和生物活性分子的构建。
• Direct Formation of 2-Substituted 2<i>H</i>-Indazoles by a Pd-Catalyzed Reaction between 2-Halobenzyl Halides and Arylhydrazines
  作者：Nayyef Aljaar、Mousa Al-Noaimi、Jürgen Conrad、Uwe Beifuss

  DOI：10.1021/acs.joc.0c01923

  日期：2021.1.15

  operationally simple method for the regioselective synthesis of 2-aryl-substituted 2H-indazoles is reported. The Pd-catalyzed reaction between easily available 2-bromobenzyl bromides and arylhydrazines employing Cs2CO3 as the base and t-Bu3PHBF4 as the ligand in DMSO at 120 °C in a sealed tube delivers the 2-substituted-2H-indazoles in a single synthetic step with yields up to 79%. The new method is based on

  报道了直接和操作简单的方法用于区域选择性合成2-芳基取代的2 H-吲唑。容易获得的2-溴苄基溴化物和芳基肼采用铯之间的Pd-催化反应2 CO 3作为碱和吨-Bu 3 PHBF 4作为在密封管中120℃下在DMSO中配体递送2-取代- 2 ħ -吲唑在单个合成步骤中的收率高达79％。该新方法基于区域选择性的分子间N-苄基化，然后进行分子内N-芳基化和氧化。
• Synthesis of 2<i>H</i>-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes
  作者：Yuesi Fang、Chunrui Wu、Richard C. Larock、Feng Shi

  DOI：10.1021/jo201605v

  日期：2011.11.4

  A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields this protocol, and subsequent Pd-catalyzed coupling reactions can be applied to the halogenated products to generate a structurally diverse library of indazoles.
• Selective Synthesis of Indazolo[2,3‐ <i>a</i> ]quinolines via Rh(III)‐Catalyzed Oxidant‐Free [4+2] or [5+1] Annulation of 2‐Aryl‐2 <i>H</i> ‐indazoles with <i>α</i> ‐Diazo Carbonyl Compounds
  作者：Shenghai Guo、Lincong Sun、Xuzhuo Li、Xinying Zhang、Xuesen Fan

  DOI：10.1002/adsc.201901422

  日期：2020.2.21

  A selective synthesis of 5,6‐disubstituted and 5‐substituted indazolo[2,3‐a]quinolines through a Rh(III)‐catalyzed oxidant‐free annulation of 2‐aryl‐2H‐indazoles with α‐diazo carbonyl compounds is reported. With 2‐aryl‐2H‐indazoles as the substrates, α‐diazo carbonyl compounds could act as a C2 synthon to afford 5,6‐disubstituted indazolo[2,3‐a]quinolines via a Rh(III)‐catalyzed [4+2] annulation. On

  通过Rh（III）催化的2-芳基-2 H-吲唑与α-重氮羰基化合物的无氧化剂环氧化反应选择性合成5,6-二取代和5-取代的吲唑并[2,3- a ]喹啉是报告。以2-芳基-2 H-吲唑为底物，α-重氮羰基化合物可作为C2合成子，通过Rh（III）催化[ 5,6-二取代的吲唑并[2,3- a ]喹啉] [4 +2]。另一方面，当使用2-芳基-3-甲酰基-2 H-吲唑类作为底物时，α-重氮羰基化合物转变为C1合成子，需要经历更复杂的[5 + 1]环化工艺来提供5位取代的吲哚并[2,3- a ]喹啉。
• Charge Migration in Dicationic Electrophiles and Its Application to the Synthesis of Aza-polycyclic Aromatic Compounds
  作者：Ang Li、Patrick J. Kindelin、Douglas A. Klumpp

  DOI：10.1021/ol060125u

  日期：2006.3.1

  Superacid-promoted reactions of dicationic electrophiles have been studied, and the positive charge centers are found to migrate apart in a predictable manner. Using isotopic labeling the charge migration is found in one system to occur through successive deprotonation-reprotonation steps. The charge migration chemistry is the basis for new general synthetic route to aza-polycyclic aromatic compounds.