(3R,5R,9R)-3,7,9-triphenyl-1,4,6-trioxaspiro[4.5]dec-7-ene | 165306-49-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,5R,9R)-3,7,9-triphenyl-1,4,6-trioxaspiro[4.5]dec-7-ene
• CAS: 165306-49-0
• 化学式: C₂₅H₂₂O₃
• 分子量: 370.448
• InChiKey: MVVJRNZTZUOJGP-HVCNVCAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5R,9R)-3,7,9-triphenyl-1,4,6-trioxaspiro[4.5]dec-7-ene 在 氢氧化钾 、 acid ion-exchange resin 、 四丁基溴化铵 作用下， 生成 (S)-3,5-Diphenyl-5-oxopentanoic acid
  参考文献：
  名称：

  Transformations of isoxazolidine and dihydropyran derivatives to optically active compounds

  摘要：

  Isoxazolidine and dihydropyran spiro derivatives can be easily transformed, by hydrolysis and hydrogenolysis, to give delta-keto esters, delta-keto acids, beta-amino esters, beta-amino acids and 3-amino alcohols in good yields, Starting from optically active compounds enantiomerically pure products are obtained, In some cases, reactions were induced by microwave irradiation.

  DOI：

  10.1039/p19960000259
• 作为产物：
  描述：

  (R)-2-methylene-4-phenyl-1,3-dioxolane 、 反式-查耳酮 反应 0.05h， 生成 (3R,5R,9S)-3,7,9-triphenyl-1,4,6-trioxaspiro[4.5]dec-7-ene 、 (3R,5R,9R)-3,7,9-triphenyl-1,4,6-trioxaspiro[4.5]dec-7-ene 、 、 (3R,5S,9S)-3,7,9-triphenyl-1,4,6-trioxaspiro[4.5]dec-7-ene
  参考文献：
  名称：

  Facial Selectivity in Cycloadditions of a Chiral Ketene Acetal under Microwave Irradiation in Solvent-Free Conditions. Configurational Assignment of the Cycloadducts by NOESY Experiments and Molecular Mechanics Calculations

  摘要：

  (R)-4-Phenyl-2-methylene-1,3-dioxolane (1) undergoes 1,3-dipolar and Diels-Alder cycloadditions under microwave irradiation within 3 min with excellent yields, a simple purification procedure, and an interesting facial selectivity. The stereochemistry of these cycloadducts has been inferred by NOESY experiments and molecular mechanics calculations. X-ray structure determination was required in one case. Thermal isomerization of the cycloadducts was performed affecting only the spiro-carbon. The Diels-Alder adducts in the presence of a slight amount of acid yield the corresponding open chain esters.

  DOI：

  10.1021/jo00118a037

文献信息

• Facial Selectivity in Cycloadditions of a Chiral Ketene Acetal under Microwave Irradiation in Solvent-Free Conditions. Configurational Assignment of the Cycloadducts by NOESY Experiments and Molecular Mechanics Calculations
  作者：Angel Diaz-Ortiz、Enrique Diez-Barra、Antonio de la Hoz、Pilar Prieto、Andres Moreno、Fernando Langa、Thierry Prange、Alain Neuman

  DOI：10.1021/jo00118a037

  日期：1995.6

  (R)-4-Phenyl-2-methylene-1,3-dioxolane (1) undergoes 1,3-dipolar and Diels-Alder cycloadditions under microwave irradiation within 3 min with excellent yields, a simple purification procedure, and an interesting facial selectivity. The stereochemistry of these cycloadducts has been inferred by NOESY experiments and molecular mechanics calculations. X-ray structure determination was required in one case. Thermal isomerization of the cycloadducts was performed affecting only the spiro-carbon. The Diels-Alder adducts in the presence of a slight amount of acid yield the corresponding open chain esters.
• Transformations of isoxazolidine and dihydropyran derivatives to optically active compounds
  作者：Angel Díaz-Ortiz、Enrique Díez-Barra、Antonio de la Hoz、Pilar Prieto、Andrés Moreno

  DOI：10.1039/p19960000259

  日期：——

  Isoxazolidine and dihydropyran spiro derivatives can be easily transformed, by hydrolysis and hydrogenolysis, to give delta-keto esters, delta-keto acids, beta-amino esters, beta-amino acids and 3-amino alcohols in good yields, Starting from optically active compounds enantiomerically pure products are obtained, In some cases, reactions were induced by microwave irradiation.