(2R,3R,4R)-1,2:3,4-diisopropylidenedioxynonane | 172490-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R)-1,2:3,4-diisopropylidenedioxynonane
• 英文别名: (4R,5R)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-5-pentyl-1,3-dioxolane
• CAS: 172490-52-7
• 化学式: C₁₅H₂₈O₄
• 分子量: 272.385
• InChiKey: JWKCIEOORGUGDQ-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-1,2:3,4-diisopropylidenedioxynonane 在 过碘酸 作用下， 以 乙醚 为溶剂， 生成 (4R^*,5R^*)-2,2-dimethyl-5-n-pentyl-1,3-dioxolane-4-carboxaldehyde
  参考文献：
  名称：

  The first synthesis of all possible stereoisomers of the (E)-4,5-dihydroxydec-2-enal, in homochiral form

  摘要：

  The first synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product of microsomal lipid peroxidation, is accomplished starting with D- and L-arabinose, D-ribose and D-lyxose by an identical reaction sequence. Each pentose was diacetonised and subjected to a Wittig reaction for the introduction of a four carbon chain. A selective cleavage of the terminal isopropylidene acetal and the oxidation of the diolic system affords a noraldehyde which is treated with (formylmethylene)triphenylphosphorane to afford the target molecule after regeneration of the diolic system.

  DOI：

  10.1016/0957-4166(95)00312-d
• 作为产物：
  描述：

  (2R,3R,4R)-1,2:3,4-diisopropylidenedioxynon-5-ene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (2R,3R,4R)-1,2:3,4-diisopropylidenedioxynonane
  参考文献：
  名称：

  The first synthesis of all possible stereoisomers of the (E)-4,5-dihydroxydec-2-enal, in homochiral form

  摘要：

  The first synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product of microsomal lipid peroxidation, is accomplished starting with D- and L-arabinose, D-ribose and D-lyxose by an identical reaction sequence. Each pentose was diacetonised and subjected to a Wittig reaction for the introduction of a four carbon chain. A selective cleavage of the terminal isopropylidene acetal and the oxidation of the diolic system affords a noraldehyde which is treated with (formylmethylene)triphenylphosphorane to afford the target molecule after regeneration of the diolic system.

  DOI：

  10.1016/0957-4166(95)00312-d

文献信息

• The first synthesis of all possible stereoisomers of the (E)-4,5-dihydroxydec-2-enal, in homochiral form
  作者：Pietro Allevi、Pierangela Ciuffreda、Giorgio Tarocco、Mario Anastasia

  DOI：10.1016/0957-4166(95)00312-d

  日期：1995.9

  The first synthesis of the four possible isomers of (E)-4,5-dihydroxydec-2-enal, a cytotoxic product of microsomal lipid peroxidation, is accomplished starting with D- and L-arabinose, D-ribose and D-lyxose by an identical reaction sequence. Each pentose was diacetonised and subjected to a Wittig reaction for the introduction of a four carbon chain. A selective cleavage of the terminal isopropylidene acetal and the oxidation of the diolic system affords a noraldehyde which is treated with (formylmethylene)triphenylphosphorane to afford the target molecule after regeneration of the diolic system.