3-[(4S,5S,6S)-5-[(E)-4,4-dimethylpent-2-en-2-yl]-5-hydroxy-2,2,4,6-tetramethyl-1,3-dioxan-4-yl]propanenitrile | 296759-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(4S,5S,6S)-5-[(E)-4,4-dimethylpent-2-en-2-yl]-5-hydroxy-2,2,4,6-tetramethyl-1,3-dioxan-4-yl]propanenitrile
• CAS: 296759-52-9
• 化学式: C₁₈H₃₁NO₃
• 分子量: 309.449
• InChiKey: XHKAEGSNWOGQQE-RXLBVGCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(4S,5S,6S)-5-[(E)-4,4-dimethylpent-2-en-2-yl]-5-hydroxy-2,2,4,6-tetramethyl-1,3-dioxan-4-yl]propanenitrile 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以99%的产率得到(E,4S,5S)-4,5-dihydroxy-5-[(1S)-1-hydroxyethyl]-4,6,8,8-tetramethylnon-6-enenitrile
  参考文献：
  名称：

  1,4-Hydrogen Radical Transfer as a New and Versatile Tool for the Synthesis of Enantiomerically Pure 1,2,3-Triols

  摘要：

  [GRAPHICS]1,4-Hydrogen radical transfers can now be reliably envisaged in radical synthetic chemistry as demonstrated by the formation of the cyano derivative II from I. Due to related sequences involving this new translocation process, followed by a highly diastereoselective trapping of the resulting anomeric radical, access to intriguing enantiopure 1,2,3-triols such as III is available.

  DOI：

  10.1021/ol000133p
• 作为产物：
  描述：

  3-[(4Z,5S,6S,10S)-4-(2,2-dimethylpropylidene)-2,2,6,8,8,10-hexamethyl-1,7,9-trioxa-2-silaspiro[4.5]decan-6-yl]propanenitrile 在 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以85%的产率得到3-[(4S,5S,6S)-5-[(E)-4,4-dimethylpent-2-en-2-yl]-5-hydroxy-2,2,4,6-tetramethyl-1,3-dioxan-4-yl]propanenitrile
  参考文献：
  名称：

  1,4-Hydrogen Radical Transfer as a New and Versatile Tool for the Synthesis of Enantiomerically Pure 1,2,3-Triols

  摘要：

  [GRAPHICS]1,4-Hydrogen radical transfers can now be reliably envisaged in radical synthetic chemistry as demonstrated by the formation of the cyano derivative II from I. Due to related sequences involving this new translocation process, followed by a highly diastereoselective trapping of the resulting anomeric radical, access to intriguing enantiopure 1,2,3-triols such as III is available.

  DOI：

  10.1021/ol000133p

文献信息

• 1,4-Hydrogen Radical Transfer as a New and Versatile Tool for the Synthesis of Enantiomerically Pure 1,2,3-Triols
  作者：Mihaela Gulea、Juan Manuel López-Romero、Louis Fensterbank、Max Malacria

  DOI：10.1021/ol000133p

  日期：2000.8.1

  [GRAPHICS]1,4-Hydrogen radical transfers can now be reliably envisaged in radical synthetic chemistry as demonstrated by the formation of the cyano derivative II from I. Due to related sequences involving this new translocation process, followed by a highly diastereoselective trapping of the resulting anomeric radical, access to intriguing enantiopure 1,2,3-triols such as III is available.