diethyl 1-benzyl-3,5-pyrazoledicarboxylate | 115414-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl 1-benzyl-3,5-pyrazoledicarboxylate
• 英文别名: diethyl 1-benzylpyrazole-3,5-dicarboxylate；1-Benzyl-1H-pyrazole-3,5-dicarboxylic acid diethyl ester
• CAS: 115414-02-3
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: PTUYOKYXVZEOPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  diethyl 1-benzyl-3,5-pyrazoledicarboxylate 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 13,26-dibenzyl-3,6,9,12,13,16,19,22,25,26-decaazatricyclo-[22.2.1.1^11,14]-octacosa-1(27),11,14(28),24-tetraene
  参考文献：
  名称：

  Synthesis and Protonation Behavior of 26-Membered Oxaaza and Polyaza Macrocycles Containing Two Heteroaromatic Units of 3,5-Disubstituted Pyrazole or 1-Benzylpyrazole. A Potentiometric and ¹H and ¹³C NMR Study

  摘要：

  The synthesis and acid-base behavior of two series of 26-membered dioxatetraamine and hexaamine heterocyclophanes containing two nuclei of either pyrazole (4a and 6a) or 1-benzylpyrazole (4b and 6b), respectively, are reported. Dipodal (2 + 2) condensations of 3,5-pyrazoledicarbaldehyde 2a or its 1-benzyl derivative 2b with 1,5-diamino-3-oxapentane afford in both cases the stable Schiff bases 3a,b in 90% yield, which after reduction with NaBH4 gave 4a;b in 75% and 84% yield, respectively. Condensation of 2a with diethylenetriamine leads to a complex mixture containing imidazolidine isomers, which was reduced in situ to afford 6a in 30% yield. Condensation of 2b with the same amine gave the stable diimidazolidine derivative 5b, which after crystallization was isolated as a pure compound in 80% yield and fully identified from analytical and H-1 and C-13 NMR data as a constitutional isomer with both imidazolidine rings located at the side of the pyrazole closer to the benzylic substituents. Reduction of 5b with NaBH4 afforded the polyamine 6b in 86% yield. Protonation constants of 4a,b and 6a,b have been determined by potentiometric methods in the pH 2-11 range, and their protonation sequences were established by a H-1 and C-13 NMR study in D2O at variable pH. For each compound, the number of protonation constants equals the number of nitrogens in the side chains. In the pH range studied, the pyrazole rings are not involved in protonation or deprotonation processes.

  DOI：

  10.1021/jo981699i
• 作为产物：
  描述：

  diethyl 4,5-dihydro-1H-pyrazole-3,5-dicarboxylate 在 溴 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 diethyl 1-benzyl-3,5-pyrazoledicarboxylate
  参考文献：
  名称：

  Synthesis, cytostatic and trichomonacide activities of 3,5-bis-(halomethyl)pyrazoles

  摘要：

  DOI：

  10.1016/0223-5234(87)90034-1

文献信息

• Bueno, Jose M.; Navarro, Pilar; Rodriguez-Franco, M. Isabel, Journal of Chemical Research, Miniprint, 1991, # 5, p. 1101 - 1116
  作者：Bueno, Jose M.、Navarro, Pilar、Rodriguez-Franco, M. Isabel、Samat, A.

  DOI：——

  日期：——
• Fierros, Marta; Rodriguez-Franco, Maria Isabel; Navarro, Pilar, Heterocycles, 1993, vol. 36, # 9, p. 2019 - 2034
  作者：Fierros, Marta、Rodriguez-Franco, Maria Isabel、Navarro, Pilar、Conde, Santiago

  DOI：——

  日期：——
• Synthesis and Protonation Behavior of 26-Membered Oxaaza and Polyaza Macrocycles Containing Two Heteroaromatic Units of 3,5-Disubstituted Pyrazole or 1-Benzylpyrazole. A Potentiometric and ¹H and ¹³C NMR Study
  作者：Vicente J. Arán、Manoj Kumar、José Molina、Laurent Lamarque、Pilar Navarro、Enrique García-España、José A. Ramírez、Santiago V. Luis、Beatriz Escuder

  DOI：10.1021/jo981699i

  日期：1999.8.1

  The synthesis and acid-base behavior of two series of 26-membered dioxatetraamine and hexaamine heterocyclophanes containing two nuclei of either pyrazole (4a and 6a) or 1-benzylpyrazole (4b and 6b), respectively, are reported. Dipodal (2 + 2) condensations of 3,5-pyrazoledicarbaldehyde 2a or its 1-benzyl derivative 2b with 1,5-diamino-3-oxapentane afford in both cases the stable Schiff bases 3a,b in 90% yield, which after reduction with NaBH4 gave 4a;b in 75% and 84% yield, respectively. Condensation of 2a with diethylenetriamine leads to a complex mixture containing imidazolidine isomers, which was reduced in situ to afford 6a in 30% yield. Condensation of 2b with the same amine gave the stable diimidazolidine derivative 5b, which after crystallization was isolated as a pure compound in 80% yield and fully identified from analytical and H-1 and C-13 NMR data as a constitutional isomer with both imidazolidine rings located at the side of the pyrazole closer to the benzylic substituents. Reduction of 5b with NaBH4 afforded the polyamine 6b in 86% yield. Protonation constants of 4a,b and 6a,b have been determined by potentiometric methods in the pH 2-11 range, and their protonation sequences were established by a H-1 and C-13 NMR study in D2O at variable pH. For each compound, the number of protonation constants equals the number of nitrogens in the side chains. In the pH range studied, the pyrazole rings are not involved in protonation or deprotonation processes.
• Synthesis, cytostatic and trichomonacide activities of 3,5-bis-(halomethyl)pyrazoles
  作者：Laura Iturrino、Pilar Navarro、María Isabel Rodríguez-Franco、Mercedes Contreras、JoséAntonio Escario、Antonio Martinez、María del Rosario Pardo

  DOI：10.1016/0223-5234(87)90034-1

  日期：1987.9