4,5-Dihydro-2,3-diphenyl-2H-benzindazole | 114382-92-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-Dihydro-2,3-diphenyl-2H-benzindazole
• 英文别名: 4,5-dihydro-2,3-diphenyl-2H-benzo[g]indazole；3-(4-methoxyphenyl)-2-phenyl-4,5-dihydro-2H-benzo[g]indazole；2,3-diphenyl-4,5-dihydro-2H-benzo[g]indazole；2,3-diphenyl-4,5-dihydro-2H-benz[g]indazole；2,3-Diphenyl-4,5-dihydro-2H-benz[g]indazol；2,3-diphenyl-4,5-dihydro-2H-benzo[g]indazole；2,3-diphenyl-4,5-dihydrobenzo[g]indazole
• CAS: 114382-92-2
• 化学式: C₂₃H₁₈N₂
• 分子量: 322.409
• InChiKey: AFNBUGXAZQWXNO-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  528.6±29.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3,3a,4,5-tetrahydro-2,3-diphenyl-2H-benzo[g]indazole 在 copper dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 0.42h， 以94%的产率得到4,5-Dihydro-2,3-diphenyl-2H-benzindazole
  参考文献：
  名称：

  使用I2 / DMSO，CuCl2 / DMSO和N-溴代琥珀酰亚胺对3,3a，4,5-四氢-3-芳基-2-苯基-2H-苯并[g]吲唑的芳香化和卤化作用

  摘要：

  用I 2 / DMSO处理3,3a，4,5-四氢-3-3-芳基-2-苯基-2 H-苯并[g]吲唑4也会导致五元环的氧化（5）N-苯基部分的碘化以及五元环的氧化（6）。但是，4与CuCl 2 / DMSO的反应仅产生化合物5。N-溴代琥珀酰亚胺（NBS）与化合物4的反应导致完全芳构化，以及吲唑环的C-5处溴化（7）。化合物5和5中的吲唑六元环6通过使用NBS（溴化沿也经历芳构7和8）。

  DOI：

  10.1002/jhet.1049

文献信息

• Cyclocondensation of Arylhydrazines with 1,3-Bis(het)arylmonothio-1,3-diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 1-Aryl-3,5-bis(het)arylpyrazoles with Complementary Regioselectivity
  作者：S. Vijay Kumar、Santosh K. Yadav、B. Raghava、B. Saraiah、H. Ila、K. S. Rangappa、Arpan Hazra

  DOI：10.1021/jo400599e

  日期：2013.5.17

  Two efficient highly regioselective routes for the synthesis of unsymmetrically substituted 1-aryl-3,5-bis(het)arylpyrazoles with complementary regioselectivity starting from active methylene ketones have been reported. In the first protocol, the newly synthesized 1,3-bis(het)aryl-monothio-1,3-diketone precursors (prepared by condensation of active methylene ketones with het(aryl) dithioesters in the presence of sodium hydride) were reacted with arylhydrazines in refluxing ethanol under neutral conditions, furnishing 1-aryl-3,5-bis(het)arylpyrazoles 7, in which the het(aryl) moiety attached to the thiocarbonyl group of monothio-1,3-diketones is installed at the 3-position. In the second method, the corresponding 3-(methylthio)-1,3-bis(het)aryl-2-propenones (prepared in situ by base-induced alkylation of 1,3-monothiodiketones) were condensed with arylhydrazines in the presence of potassium tert-butoxide in. refluxing tert-butyl alcohol, yielding 1-aryl-3,5-bis(het)arylpyrazoles 9 with complementary regioselectivity (method A). The efficiency of this protocol was further improved by developing a one-pot, three-component procedure for the synthesis of pyrazoles 9, directly from active methylene ketones, by reacting in situ generated 3-(methylthio)-1,3-bis(het)aryl-2-propenones with arylhydrazines in the presence of sodium hydride (instead of potassium tert-butoxide as base). The structures and regiochemistry of newly synthesized pyrazoles were confirmed from their spectral and analytical data along with X-ray crystallographic data of three pairs of regioisomers.
• Isomerization of substituted tricyclic 4,5-dihydropyrazoles
  作者：T. L�r�nd、F. Aradi、�. Sz�ll�sy、G. T�th、T. K�nya

  DOI：10.1007/bf00807038

  日期：——

  The acid and base catalyzed isomerization of some tricyclic 2-pyrazolines with N-Carbamoyl-, N-thiocarbamoyl- and N-phenyl substituents was investigated. Starting from cis or trans 3-H, 3a-H diastereomers, equilibrium mixtures of cis and tl ans diastereomers were prepared which were separated and subsequently studied by H-1 NMR and C-13 NMR spectroscopy. A mechanism for the isomerization of the pyrazolines is suggested, supported by a deuterium exchange at C-3a.