(2R,4R)-1-cyano-6-phenyl-2,4-bis(trimethylsiloxy)hexane | 135943-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,4R)-1-cyano-6-phenyl-2,4-bis(trimethylsiloxy)hexane
• 英文别名: (3R,5R)-7-phenyl-3,5-bis(trimethylsilyloxy)heptanenitrile
• CAS: 135943-95-2
• 化学式: C₁₉H₃₃NO₂Si₂
• 分子量: 363.648
• InChiKey: MMNXOJGQKVKLGW-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,4S)-1,2:4,5-dianhydro-3-deoxypentitol 在 potassium cyanide 、 18-冠醚-6 、 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 3.42h， 生成 (2R,4R)-1-cyano-6-phenyl-2,4-bis(trimethylsiloxy)hexane
  参考文献：
  名称：

  Optically pure 1,3-diols from (2R,4R)- and (2S,4S)-1,2:4,5-diepoxypentane

  摘要：

  Optically pure (> 97% ee) (2R,4R)-1,2:4,5-diepoxypentane (1) and its enantiomer can be prepared in three steps from 2,4-pentanedione without the need for chromatographic purification. Diepoxide 1 is an efficient precursor to a wide variety of optically pure syn and anti 1,3-diols. Reaction with excess nucleophile gives symmetric[GRAPHICS]anti 1,3-diols in good yield. Reaction with a slight excess of alkyllithium under Ganem's conditions gives the monoepoxides 5 in good yield. Addition of a second nucleophile to monoepoxide 5 gives asymmetric anti 1,3-diols. Mitsunobu inversion of monoepoxide 5 followed by addition of a second nucleophile gives syn 1,3-diols. Optically pure syn and anti 1,3-diols are available from diepoxide 1 in one to three steps and good overall yield.

  DOI：

  10.1021/jo00017a032