(E,4R,5S)-4,5-isopropylidenedioxydec-2-enal | 172490-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,4R,5S)-4,5-isopropylidenedioxydec-2-enal
• 英文别名: (E)-3-[(4R,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl]prop-2-enal
• CAS: 172490-53-8
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: FHMMEWRRIANRBL-MJEUXHFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E,4R,5S)-4,5-isopropylidenedioxydec-2-enal 在 三氟乙酸 作用下， 反应 0.5h， 以57%的产率得到(E,4R,5S)-4,5-dihydroxydec-2-enal
  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,3S,4S)-1,2:3,4-diisopropylidenedioxynonane 在 过碘酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 (E,4R,5S)-4,5-isopropylidenedioxydec-2-enal
  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.