4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]butanal | 160226-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]butanal
• CAS: 160226-45-9
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: HOFKJAPJTNCNJQ-MRVPVSSYSA-N

物化性质

• 沸点：
  233.2±15.0 °C(predicted)
• 密度：
  0.972±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]butanal 在 sodium hydroxide 、 重铬酸吡啶 、 Amberlyst 15 、 4 A molecular sieve 、 草酸 、 silver nitrate 作用下， 反应 9.0h， 生成 (R)-5-formyl δ-valerolactone
  参考文献：
  名称：

  5-formyl-δ—valerolactone : A useful synthon for the chiral synthesis of the vespa orientalis pheromone and the mosquito oviposition attractant pheromone

  摘要：

  A synthetic scheme starting from the reaction between the lithiated N-allyl-N-methyl-(bisdimethylamino)phosphoramide anion and the triflate derivative of (R)-(-)- or (S)-(+)-2,3-O-isopropylideneglycerol is described to prepare the key chiral synthon (R)-5- or (S)-5-formyl-delta-valerolactone that leads to the title compounds.

  DOI：

  10.1016/s0040-4039(00)74412-1
• 作为产物：
  描述：

  [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate 在 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 生成 4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]butanal
  参考文献：
  名称：

  5-formyl-δ—valerolactone : A useful synthon for the chiral synthesis of the vespa orientalis pheromone and the mosquito oviposition attractant pheromone

  摘要：

  A synthetic scheme starting from the reaction between the lithiated N-allyl-N-methyl-(bisdimethylamino)phosphoramide anion and the triflate derivative of (R)-(-)- or (S)-(+)-2,3-O-isopropylideneglycerol is described to prepare the key chiral synthon (R)-5- or (S)-5-formyl-delta-valerolactone that leads to the title compounds.

  DOI：

  10.1016/s0040-4039(00)74412-1

文献信息

• Structural Determination of Montanacin D by Total Synthesis
  作者：Shunya Takahashi、Yayoi Hongo、Yuki Tsukagoshi、Hiroyuki Koshino

  DOI：10.1021/ol801576z

  日期：2008.10.2

  The first total syntheses of acetogenin 3 and its 4S,8R-isomer are described. The key step involves intermolecular metathesis of an alpha,beta-unsaturated ketone carrying a tetra hydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.