dimethyl 1,5-diphenylpyrazole-3,4-dicarboxylate | 67491-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl 1,5-diphenylpyrazole-3,4-dicarboxylate
• 英文别名: dimethyl 1,5-diphenyl-1H-pyrazole-3,4-dicarboxylate；1,5-Diphenyl-3,4-dicarbomethoxy-pyrazol；1,5-Diphenyl-3,4-pyrazoldicarbonsaeure-dimethylester；1,5-Diphenyl-pyrazol-3,4-dicarbonsaeure-dimethylester；1,5-diphenyl-1H-pyrazole-3,4-dicarboxylic acid dimethyl ester；1,5-Diphenyl-1H-pyrazol-3,4-dicarbonsaeure-dimethylester
• CAS: 67491-64-9
• 化学式: C₁₉H₁₆N₂O₄
• 分子量: 336.347
• InChiKey: ZPANPHXREPYSIW-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• 沸点：
  494.6±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 1,5-diphenylpyrazole-3,4-dicarboxylate 在 肼 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以73%的产率得到2,3-diphenyl-5,6-dihydro-2H-pyrazolo[3,4-d]pyridazine-4,7-dione
  参考文献：
  名称：

  1,5-二苯基-1H-吡唑-3,4-二羧酸的吡唑衍生物的合成与表征

  摘要：

  4，（乙氧基羰基）-1,5-二苯基-1 H-吡唑-3-羧酸2的化合物是由4,5-二氧杂-2-苯基-4,5-二氢呋喃-3-羧酸乙酯反应制得的和1-亚苄基-2-苯基肼。许多替代吡唑的二羧酸衍生物（的4，图5a，图5b，图5c，6，7，8，图9a，图9b，图9c，图9d，图9e，9f中，9克，9H，9I，9J，9K，9升，9米，10，11，12，13，14）是从1,5-二苯基-1-合成ħ吡唑-3,4-二羧酸3，将其从碱性水解制备2。合成的化合物的结构通过1 H NMR，13 C NMR，质量，FTIR和元素分析进行表征。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.416
• 作为产物：
  描述：

  3,4-二(苯基)恶二唑-3-鎓-5-醇 生成 dimethyl 1,5-diphenylpyrazole-3,4-dicarboxylate
  参考文献：
  名称：

  MAERKY M.; MEIER H.; WUNDERLI A.; HEIMGARTNER H.; SCHMID H.; HANSEN H.-J., HELV. CHIM, ACTA, 1978, 61, NO 4, 1477-1510

  摘要：

  DOI：

文献信息

• Synthesis of 4-Fluoromethylsydnones and their Participation in Alkyne Cycloaddition Reactions
  作者：Robert S. Foster、Harry Adams、Harald Jakobi、Joseph P. A. Harrity

  DOI：10.1021/jo400381a

  日期：2013.4.19

  We report the synthesis and some structural studies of 4-trifluoromethyl, 4-difluoromethyl-, and 4-monofluoromethylsydnones. All but the latter compounds are stable and represent effective precursors to a range of pyrazoles after cycloaddition reactions with alkynes. The cycloadditions are generally highly regioselective and provide 5-fluoromethylpyrazole products, although we have observed that Bn-substituted

  我们报告了4-三氟甲基，4-二氟甲基-和4-单氟甲基sydnones的合成和一些结构研究。除后者以外的所有化合物都是稳定的，并且在与炔烃进行环加成反应后，代表了一系列吡唑的有效前体。尽管我们已经观察到Bn取代的sydnones可以提供意想不到的炔烃插入模式以生成3-氟甲基异构体，但是环加成物通常具有高度的区域选择性并提供5-氟甲基吡唑产物。
• Palladium-Catalysed Direct Arylation of Sydnones
  作者：Wesley Moran、Arantxa Rodriguez

  DOI：10.1055/s-0028-1083344

  日期：2009.2

  Conditions for the palladium-catalysed direct arylation of sydnones with aryl iodides and bromides are revealed.

  揭示了钯催化下，锡内酰酮与碘代芳烃和溴代芳烃直接偶联反应的条件。
• v. Auwers; Mauss, Chemische Berichte, 1926, vol. 59, p. 612
  作者：v. Auwers、Mauss

  DOI：——

  日期：——
• Rhodium-Catalyzed Addition–Cyclization of Hydrazines with Alkynes: Pyrazole Synthesis via Unexpected C–N Bond Cleavage
  作者：Deng Yuan Li、Xiao Feng Mao、Hao Jie Chen、Guo Rong Chen、Pei Nian Liu

  DOI：10.1021/ol501402p

  日期：2014.7.3

  Rhodium-catalyzed addition-cyclization of hydrazines with alkynes has been achieved to afford highly substituted pyrazoles under mild conditions. The cascade reaction involves two transformations: addition of the C-N bond of hydrazines to alkynes via unexpected C-N bond cleavage and intramolecular dehydration cyclization.
• Nucleophilic β-Oniovinylation:  Concept, Mechanism, Scope, and Applications
  作者：Robert Weiss、Matthias Bess、Stefan M. Huber、Frank W. Heinemann

  DOI：10.1021/ja071316a

  日期：2008.4.1

  Insertion of an electron-deficient alkyne A-C C-A (A = CO(2)Me) into the C-L(+) bond of an acyl-onio salt R-C(O)-L(+) (R = Ar, OAlk; L = 4-dimethylaminopyridine, PPh(3)) has for the first time been achieved in the presence of catalytic amounts of the nucleophile L. For R = OMe, a second insertion of the alkyne was observed. X-ray structures were obtained for a number of such -oniovinylation products. Depending on reaction conditions, preferentially E- or Z-stereochemistry was observed, the Z-isomer being the thermodynamically more stable. A mechanism for this novel insertion reaction is presented which accounts for the topology of the products and rationalizes the observed stereochemistry. The beta-onio-activated Michael systems thus generated represent a virtually unexplored class of compounds. The onio substituent in such compounds can be selectively replaced by a number of nucleophiles. Thus a series of Michael systems with donor functions in the beta-position is easily synthesized. These compounds represent a source for useful further transformations, for example, cyclizations to quinolones, thiochromones, and pyrazoles.