(3S,5R,8R)-2,3,8-triphenyl-1,6,9-trioxa-2-azaspiro[4.4]nonane | 165132-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3S,5R,8R)-2,3,8-triphenyl-1,6,9-trioxa-2-azaspiro[4.4]nonane
• CAS: 165132-81-0
• 化学式: C₂₃H₂₁NO₃
• 分子量: 359.425
• InChiKey: NPULYDDGAFGYSB-RJGXRXQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5R,8R)-2,3,8-triphenyl-1,6,9-trioxa-2-azaspiro[4.4]nonane 在 palladium on activated charcoal sodium tetrahydroborate 、 甲酸铵 作用下， 生成 (S)-3-Anilino-3-phenylpropanol
  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：

  (3S,5S,8R)-2,3,8-triphenyl-1,6,9-trioxa-2-azaspiro[4.4]nonane 以 氘代二甲亚砜 为溶剂， 反应 2.0h， 生成 (3S,5R,8R)-2,3,8-triphenyl-1,6,9-trioxa-2-azaspiro[4.4]nonane
  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

• Determination of the Stereochemistry of Four Spirodiastereoisomers by One- and Two-Dimensional NOE Studies
  作者：A. Moreno、A. Díaz-Ortiz、E. Díez-Barra、A. de la Hoz、F. Langa、P. Prieto、T. D. W. Claridge

  DOI：10.1002/(sici)1097-458x(199601)34:1<52::aid-omr829>3.0.co;2-2

  日期：1996.1

  The stereochemistries of four cycloadducts obtained by 1,3‐dipolar reactions were investigated with one‐ and two‐dimensional NMR techniques. Analysis of a series of homonuclear NOE difference spectra and COSY and NOESY spectra recorded in a variety of solvents and at various temperatures allowed the determination of the full stereochemistry of each adduct.

  用一维和二维核磁共振技术研究了通过 1,3-偶极反应获得的四种环加合物的立体化学。在各种溶剂和各种温度下记录的一系列同核 NOE 差异光谱以及 COZY 和 NOESY 光谱的分析允许确定每个加合物的完整立体化学。
• 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.