2-exo-2-(3-fluorophenyl)-1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazine-3,3-dicarbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-exo-2-(3-fluorophenyl)-1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazine-3,3-dicarbonitrile
• 英文别名: exo-2-(3-fluorophenyl)-3,3-dicyano-1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazine；(2R,10bR)-2-(3-fluorophenyl)-2,10b-dihydro-1H-pyrrolo[2,1-a]phthalazine-3,3-dicarbonitrile
• 化学式: C₁₉H₁₃FN₄
• 分子量: 316.337
• InChiKey: WIBCCXXMVXFYJB-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氟苯乙烯 、 phthalazinium-2-dicyanomethanide 以 乙腈 为溶剂， 反应 24.0h， 以76%的产率得到2-exo-2-(3-fluorophenyl)-1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazine-3,3-dicarbonitrile
  参考文献：
  名称：

  水和Huisgen环加成反应：重点研究二氰基（酞菁）甲烷与取代的苯乙烯和苯并亚苄基丙酮反应中过渡态的极性贡献。

  摘要：

  二氰基（酞菁-2-基-2-基-2-甲基）甲烷（1）与部分取代的苯乙烯和“亚苄基丙酮”在MeCN和H 2 O中的摩尔浓度为10 mol％的1,3-偶极环加成反应的合成和动力学研究报告了MeCN。动力学数据得到理论计算的支持。苯乙烯的主要产物为exo -2-芳基-1,2,3,10b-四氢吡咯并[2,1- a ]邻苯二甲腈3,3-二甲腈3，而'亚苄基丙酮'为1-内酯，2 -外-2-乙酰基1-芳基1,2,3,10b四氢吡咯并[2,1-一个]酞嗪-3,3-二腈7。没有迹象表明在水性环境中，环己二酮过渡态的极性比在MeCN中更强。

  DOI：

  10.1002/hlca.200590128

文献信息

• Water and theHuisgen Cycloaddition Reaction: A Focus on Polar Contributions to the Transition State in the Reactions of Dicyano(phthalazinium)methanide with Substituted Styrenes and Benzylidene Acetones
  作者：Richard N. Butler、Anthony G. Coyne、William J. Cunningham、Eamon M. Moloney、Luke A. Burke

  DOI：10.1002/hlca.200590128

  日期：2005.7

  Synthetic and kinetic studies on the 1,3-dipolar cycloaddition reactions of dicyano(phthalazin-2-ium-2-yl)methanide (1) with some substituted styrenes and ‘benzylidene acetones’ in MeCN and H2O containing 10 mol-% of MeCN are reported. The kinetic data were supported by theoretical calculations. The major products from styrenes were exo-2-aryl-1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazine-3,3-dicarbonitriles

  二氰基（酞菁-2-基-2-基-2-甲基）甲烷（1）与部分取代的苯乙烯和“亚苄基丙酮”在MeCN和H 2 O中的摩尔浓度为10 mol％的1,3-偶极环加成反应的合成和动力学研究报告了MeCN。动力学数据得到理论计算的支持。苯乙烯的主要产物为exo -2-芳基-1,2,3,10b-四氢吡咯并[2,1- a ]邻苯二甲腈3,3-二甲腈3，而'亚苄基丙酮'为1-内酯，2 -外-2-乙酰基1-芳基1,2,3,10b四氢吡咯并[2,1-一个]酞嗪-3,3-二腈7。没有迹象表明在水性环境中，环己二酮过渡态的极性比在MeCN中更强。
• Water and Organic Synthesis: A Focus on the In-Water and On-Water Border. Reversal of the In-Water Breslow Hydrophobic Enhancement of the Normal <i>endo</i>-Effect on Crossing to On-Water Conditions for Huisgen Cycloadditions with Increasingly Insoluble Organic Liquid and Solid 2π-Dipolarophiles
  作者：Richard N. Butler、Anthony G. Coyne、William J. Cunningham、Eamon M. Moloney

  DOI：10.1021/jo400055g

  日期：2013.4.5

  Measurements of the endo/exo product ratios for Huisgen cycloadditions with a series of vinyl ketones, alkyl acrylates, and substituted styrenes as dipolarophiles with phthalazinium and pyridazinium dicyanomethanide 1,3-dipoles in acetonitrile and water show that as the reactions change from in-water (large hydrophobic enhancement of endo-products) to on-water, the hydrophobic enhancement of the endo-products is reduced and partially reversed (relative to acetonitrile). An expected increase of the endo-effect with increasing hydrophobic character of the dipolarophile is overcome by decreasing water solubility causing changeover to on-water conditions. On-water reactions do not show increased cycloaddition endo-effects (relative to organic solvents) as do in-water reactions.