(3ac,9ac)-3a,4,9,9a-tetrahydro-4r,9c-ethano-3H-naphtho[2,3-c]furan-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (3ac,9ac)-3a,4,9,9a-tetrahydro-4r,9c-ethano-3H-naphtho[2,3-c]furan-1-one
• 英文别名: (1R,8S,9S,13R)-11-oxatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-trien-10-one
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: XGHWNLFATJUPRH-LOWDOPEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2(5H)-呋喃酮 、 (1-(trimethylsilyl)-1,2,3,4-tetrahydronaphth-4-yl)trimethylammonium iodide 在 potassium fluoride 作用下， 以 乙腈 为溶剂， 以17%的产率得到(3ac,9ac)-3a,4,9,9a-tetrahydro-4r,9c-ethano-3H-naphtho[2,3-c]furan-1-one
  参考文献：
  名称：

  Reactivity and endo–exo Selectivity in Diels–Alder Reaction of o-Quinodimethanes. An Experimental and DFT Computational Study

  摘要：

  endo-exo Selectivity in Diels-Alder cycloadditions of several o-quinodimethanes (1-4) with acrylonitrile, 2-(5H)-furanone and N-methylmaleimide has been investigated in acetonitrile solution. Transition structures of the cycloaddition of the parent o-QDM (1), (E,E)1,8-dimethyl-o-QDM (2), isoindene (3) and 2,3-dihydronaphthalene (4) with acrylonitrile and maleimide were located at both HF/6-31G* and B3LYP/6-31G* methods. Theoretical data reproduce fairly well both experimental absolute reaction rates and diastereoisomer ratios. The high endo selectivity has been rationalized mainly as a result of solvation effects (acetonitrile, PCM model) and reactant deformations. The latter is due to steric interactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00126-5

文献信息

• Reactivity and endo–exo Selectivity in Diels–Alder Reaction of o-Quinodimethanes. An Experimental and DFT Computational Study
  作者：Cristiana Di Valentin、Mauro Freccero、Mirko Sarzi-Amadè、Riccardo Zanaletti

  DOI：10.1016/s0040-4020(00)00126-5

  日期：2000.4

  endo-exo Selectivity in Diels-Alder cycloadditions of several o-quinodimethanes (1-4) with acrylonitrile, 2-(5H)-furanone and N-methylmaleimide has been investigated in acetonitrile solution. Transition structures of the cycloaddition of the parent o-QDM (1), (E,E)1,8-dimethyl-o-QDM (2), isoindene (3) and 2,3-dihydronaphthalene (4) with acrylonitrile and maleimide were located at both HF/6-31G* and B3LYP/6-31G* methods. Theoretical data reproduce fairly well both experimental absolute reaction rates and diastereoisomer ratios. The high endo selectivity has been rationalized mainly as a result of solvation effects (acetonitrile, PCM model) and reactant deformations. The latter is due to steric interactions. (C) 2000 Elsevier Science Ltd. All rights reserved.