(7S,8R,11R)-8-hydroxy-3,3-dimethyl-7,11-diphenyl-2,4-dioxa-spiro[5.5]undecane-1,5,9-trione | 851764-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7S,8R,11R)-8-hydroxy-3,3-dimethyl-7,11-diphenyl-2,4-dioxa-spiro[5.5]undecane-1,5,9-trione
• 英文别名: (7R,10R,11S)-10-hydroxy-3,3-dimethyl-7,11-diphenyl-2,4-dioxaspiro[5.5]undecane-1,5,9-trione
• CAS: 851764-30-2
• 化学式: C₂₃H₂₂O₆
• 分子量: 394.424
• InChiKey: ZSCWKFPDYBBTLC-QRQLOZEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (7S,8R,11R)-8-hydroxy-3,3-dimethyl-7,11-diphenyl-2,4-dioxa-spiro[5.5]undecane-1,5,9-trione 、 3,5-二硝基苯甲酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (7S,8R,11R)-8-(3,5-dinitrobenzyloxy)-3,3-dimethyl-7,11-diphenyl-2,4-dioxa-spiro[5.5]undecane-1,5,9-trione
  参考文献：
  名称：

  Direct Amino Acid-Catalyzed Asymmetric Desymmetrization of meso-Compounds:  Tandem Aminoxylation/O−N Bond Heterolysis Reactions

  摘要：

  A practical organocatalytic process for the synthesis of optically active, highly substituted (x-hydroxy-ketones was achieved through asymmetric desymmetrization (ADS) of prochiral ketones. The ADS and O-N bond reduction reaction of prochiral ketone with nitrosobenzene in the presence of a catalytic amount of chiral amine or amino acid produced the tandem ADS/O-N bond reduced products as single diastereomers with good yields and excellent enantiomeric excesses.

  DOI：

  10.1021/ol050246e
• 作为产物：
  描述：

  (7β,11β)-3,3-dimethyl-7,11-diphenyl-2,4-dioxaspiro[5.5]undecane-1,5,9-trione 在 亚硝基苯 、 L-脯氨酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以85%的产率得到(7S,8R,11R)-8-hydroxy-3,3-dimethyl-7,11-diphenyl-2,4-dioxa-spiro[5.5]undecane-1,5,9-trione
  参考文献：
  名称：

  Direct Amino Acid-Catalyzed Asymmetric Desymmetrization of meso-Compounds:  Tandem Aminoxylation/O−N Bond Heterolysis Reactions

  摘要：

  A practical organocatalytic process for the synthesis of optically active, highly substituted (x-hydroxy-ketones was achieved through asymmetric desymmetrization (ADS) of prochiral ketones. The ADS and O-N bond reduction reaction of prochiral ketone with nitrosobenzene in the presence of a catalytic amount of chiral amine or amino acid produced the tandem ADS/O-N bond reduced products as single diastereomers with good yields and excellent enantiomeric excesses.

  DOI：

  10.1021/ol050246e