(Z)-3-[[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-ylamino]methylene]dihydrofuran-2-(3H)-one | 1345980-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (Z)-3-[[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-ylamino]methylene]dihydrofuran-2-(3H)-one
• 英文别名: (Z)-3-((3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-ylamino)methylene)dihydrofuran-2(3H)-one；(z)-3-((3-(4-Chlorophenyl)-1-phenyl-1h-pyrazol-5-ylamino)methylene)-dihydrofuran-2(3h)-one；(3Z)-3-[[[5-(4-chlorophenyl)-2-phenylpyrazol-3-yl]amino]methylidene]oxolan-2-one
• CAS: 1345980-82-6
• 化学式: C₂₀H₁₆ClN₃O₂
• 分子量: 365.819
• InChiKey: BLHGUUFBSGQPGO-SQFISAMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-[[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-ylamino]methylene]dihydrofuran-2-(3H)-one 在 三乙胺 、 三氯氧磷 作用下， 生成 2-[5-(2-chloroethyl)-3-(4-chlorophenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy]ethanol
  参考文献：
  名称：

  Use of sodium salt of cyclic β-formylester for synthesis of dihydro-2H-furo[2,3-d]pyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines

  摘要：

  The chemoselective reaction of the sodium salt of alpha-formyl-gamma-butyrolactone and 5-aminopyrazole furnished dihydrofuro[2,3-d]pyrazolo[3,4-b]pyridine at two different reaction conditions, i.e., with NH4OAc or in refluxing AcOH. The same reactants when refluxed in MeOH and AcOH produced a pyrazolylamino dihydrofuranone derivative. A mixture of 2-chloroethyl-4-chloropyrazolopyridines and dihydrofuro[2,3-d]pyrazolo[3,4-b]pyridine derivatives was obtained on refluxing the intermediate dihydrofuranone in POCl3. A one-step synthesis of tricyclic pyrazolopyrrolopyridines and thienopyrazolopyridines resulted from SNAr reaction of 2-chloroethyl-4-chloropyrazolopyridines with primary aromatic amines and with thiourea.

  DOI：

  10.1007/s00706-011-0535-1
• 作为产物：
  描述：

  5-(4-氯-苯基)-2-苯基-2H-吡唑-3-基胺 、 Na-Salzes von Tetrahydro-2-oxofuran-3-carbaldehyd 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以65%的产率得到(Z)-3-[[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-5-ylamino]methylene]dihydrofuran-2-(3H)-one
  参考文献：
  名称：

  Use of sodium salt of cyclic β-formylester for synthesis of dihydro-2H-furo[2,3-d]pyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines

  摘要：

  The chemoselective reaction of the sodium salt of alpha-formyl-gamma-butyrolactone and 5-aminopyrazole furnished dihydrofuro[2,3-d]pyrazolo[3,4-b]pyridine at two different reaction conditions, i.e., with NH4OAc or in refluxing AcOH. The same reactants when refluxed in MeOH and AcOH produced a pyrazolylamino dihydrofuranone derivative. A mixture of 2-chloroethyl-4-chloropyrazolopyridines and dihydrofuro[2,3-d]pyrazolo[3,4-b]pyridine derivatives was obtained on refluxing the intermediate dihydrofuranone in POCl3. A one-step synthesis of tricyclic pyrazolopyrrolopyridines and thienopyrazolopyridines resulted from SNAr reaction of 2-chloroethyl-4-chloropyrazolopyridines with primary aromatic amines and with thiourea.

  DOI：

  10.1007/s00706-011-0535-1

文献信息

• Synthesis of Pyrazolopyridine Annulated Heterocycles and Study the Effect of Substituents on Photophysical Properties
  作者：Shivaraj P. Patil、Deepak P. Shelar、Raghunath B. Toche

  DOI：10.1007/s10895-011-0960-x

  日期：2012.1

  pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines 7(a-n) respectively. The substituents effect at C4 position on fluorescence properties of pyrazolopyridines has been studied. Moreover the effect of electron donor and halogen substituents on fluorescence properties of pyrazolopyrrolopyridines 7(a-n) has been investigated along with their fluorescent quantum yield. Synthesis of fluorescent pyrazolo[3,4-b]pyridine

  5-氨基吡唑与环状β-甲酰酯反应合成具有4-氯-5-氯乙基侧链的吡唑并[3,4- b ]吡啶，得到氨基吡唑二氢呋喃酮中间体，在三氯氧化磷中环化仅转化为4-氯-5-氯乙基吡唑并[3,4- b ]吡啶4(ab)占主要量。侧链与乙酸、硫脲和芳香胺形成角环导致形成三环呋喃[2,3- d ]吡唑并[2,3- b ]吡啶5(ab)、吡唑并[3,4- b ]噻吩并[2,3- d ]吡啶6(ab)和吡唑并[3,4- b ]吡咯并[2,3-d ]吡啶分别为7(an)。研究了C 4位取代基对吡唑并吡啶荧光性质的影响。此外，还研究了电子供体和卤素取代基对吡唑并吡咯并吡啶7(an)荧光性质的影响及其荧光量子产率。 荧光吡唑并[3,4- b ]吡啶环化杂环的合成