3,3-cyclopentyl-3H-pyrazole-4,5-dicarboxylate | 119393-27-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,3-cyclopentyl-3H-pyrazole-4,5-dicarboxylate
• 英文别名: 3,4-bis(methoxycarbonyl)-1,2-diazaspiro<4.4>nona-1,3-diene；dimethyl-3,3-cyclopentyl-3H-pyrazole-4,5-dicarboxylate；Dimethyl 1,2-diazaspiro[4.4]nona-1,3-diene-3,4-dicarboxylate
• CAS: 119393-27-0
• 化学式: C₁₁H₁₄N₂O₄
• 分子量: 238.243
• InChiKey: XVZBADVUWCKWGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3-cyclopentyl-3H-pyrazole-4,5-dicarboxylate 以 苯 为溶剂， 反应 4.67h， 生成 dimethyl 4,5,6,7-tetrahydroindazole-2,3-dicarboxylate
  参考文献：
  名称：

  Thermal Rearrangements of 3,3-Spiroalkylated Pyrazoles: Ring Expansion and Novel Cases of Sequential 1,5-Shifts

  摘要：

  A 3,3-spiro-(cyclopentyl)pyrazole containing electron withdrawing ester groups undergoes readily ring expansion in the form of the van Alphen-Huettel rearrangement. Subsequent post van Alphen-Huettel rearrangement involved a sequence of 1,5-shifts different from that suggested earlier. Reactive intermediates have been isolated and identified. The corresponding phenyl analog does not exhibit post van Alphen-Huettel rearrangement. A rationale for the different behavior is offered. X-Ray crystallography has been applied to differentiate between structurally similar product.

  DOI：

  10.3987/com-01-9298
• 作为产物：
  描述：

  3-甲氧基-3-甲基-4-氧杂-1,2-二氮杂螺[4.4]壬-1-烯 、 丁炔二酸二甲酯 以 苯 为溶剂， 反应 5.0h， 以56%的产率得到3,3-cyclopentyl-3H-pyrazole-4,5-dicarboxylate
  参考文献：
  名称：

  Photolysis of 2-alkoxy-.DELTA.3-1,3,4-oxadiazolines. A new route to diazoalkanes

  摘要：

  DOI：

  10.1021/jo00269a019

文献信息

• Photoinduced Electron Transfer Reactions of 3,3-Dialkylated 4,5-Diphenyl-3H-Pyrazoles: A New Route to the Formation of the Solvent Adducts
  作者：Yao-Pin Yen、Tseng-Min Huang、Yu-Ping Tseng、Hsuan-Yu Lin、Ching-Cheng Lai

  DOI：10.1002/jccs.200400061

  日期：2004.4

  3,3-Dialkyl-4,5-diphenyl-3H-pyrazoles undergo readily photoinduced electron transfer (PET) reaction with 2,4,6-triphenylpyrylium tetrafluoroborate (TPP + ) in acetonitrile to produce cyclopropenes and 2H-pyrroles. During prolonged irradiation, the new ring-closure products derived from 2H-pyrroles as the secondary photoproducts are also produced. However, the corresponding ester analog exhibits different

  3,3-Dialkyl-4,5-diphenyl-3H-pyrazoles 与 2,4,6-triphenylpyrylium tetrafluoroborate (TPP + ) 在乙腈中很容易发生光诱导电子转移 (PET) 反应，生成环丙烯和 2H-吡咯。在长时间辐照过程中，还产生了以2H-吡咯为次级光产物的新型闭环产物。然而，相应的酯类似物表现出不同的行为以获得作为主要光产物的环丙烯和作为次要光产物的环丙烯的[2+2]二聚体。提供了不同行为的基本原理。
• MAJCHRZAK, MICHAEL W.;BEKHAZI, MICHEL;TSE-SHEEPY, IRENE;WARKENTIN, JOHN, J. ORG. CHEM., 54,(1989) N, C. 1842-1845
  作者：MAJCHRZAK, MICHAEL W.、BEKHAZI, MICHEL、TSE-SHEEPY, IRENE、WARKENTIN, JOHN

  DOI：——

  日期：——