(5aRS,11bRS)-3,5a,6,11b-tetrahydro-1,5,5-trimethyl-3-phenyl-5H-<1>benzopyrano<3',4':4,5>pyrano<2,3-c>pyrazole | 112296-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5aRS,11bRS)-3,5a,6,11b-tetrahydro-1,5,5-trimethyl-3-phenyl-5H-<1>benzopyrano<3',4':4,5>pyrano<2,3-c>pyrazole
• 英文别名: (1S,10R)-11,11,16-trimethyl-14-phenyl-8,12-dioxa-14,15-diazatetracyclo[8.7.0.02,7.013,17]heptadeca-2,4,6,13(17),15-pentaene
• CAS: 112296-62-5
• 化学式: C₂₂H₂₂N₂O₂
• 分子量: 346.429
• InChiKey: QDNMFCZVPVRVAA-FXAWDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  sodium salicylate 在 ethylenediamine Tetraacetic Acid 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 30.0h， 生成 (5aRS,11bRS)-3,5a,6,11b-tetrahydro-1,5,5-trimethyl-3-phenyl-5H-<1>benzopyrano<3',4':4,5>pyrano<2,3-c>pyrazole
  参考文献：
  名称：

  Intra- and intermolecular hetero-Diels-Alder reactions. 16. Stereospecificity in intramolecular hetero-Diels-Alder reactions of 2-benzylidene-1,3-dicarbonyl compounds

  摘要：

  DOI：

  10.1021/jo00384a059

文献信息

• Intra- and intermolecular hetero-Diels-Alder reactions. 17. Intramolecular hetero-Diels-Alder reaction of alkylidene- and benzylidenepyrazolones and benzylideneisoxazolones. Investigations toward the conformation of the transition state
  作者：Lutz F. Tietze、Thomas Brumby、Martina Pretor、Gerd Remberg

  DOI：10.1021/jo00239a024

  日期：1988.2
• Intramolecular Diels−Alder Reaction in Ionic Liquids: Effect of Ion-Specific Solvent Friction
  作者：Shraeddha Tiwari、Nageshwar Khupse、Anil Kumar

  DOI：10.1021/jo801802q

  日期：2008.11.21

  The present work aims at understanding the role of viscosity or solvent friction in ionic liquids for an intramolecular Diels-Alder (IMDA) reaction of (E)-1-phenyl-4-[2-(3-methyl-2-butenyloxy)benzylidene]-5-pyrazolone (1). The results have been analyzed on the basis of the current theoretical models, and their failure to account for the observed trends is discussed in terms of "effective" viscosity or microviscosity. The rates of the reaction decrease with the increasing viscosity of the ionic liquids. As evident from the anionic effect, the solute-solvent specific interactions play a role in governing the kinetics of the reaction. The lower viscosities of the bistrifluoromethanesulfonimide [NTf2](-) based ionic liquids as compared to those based on tetrafluoroborate [BF4](-) anion fail to result in a corresponding acceleration in the rates of the reaction. These contradictory results indicate that solvent microviscosity, rather than the bulk macroscopic viscosity, should be the criteria for selecting the ionic liquids as reaction media.