α-(Diisopropoxyphosphinyl)-δ-valerolactone | 151746-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: α-(Diisopropoxyphosphinyl)-δ-valerolactone
• 英文别名: 3-Di(propan-2-yloxy)phosphoryloxan-2-one
• CAS: 151746-93-9
• 化学式: C₁₁H₂₁O₅P
• 分子量: 264.259
• InChiKey: MOOOCLGYMFKMOV-UHFFFAOYSA-N

物化性质

• 沸点：
  391.1±31.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙醛 、 α-(Diisopropoxyphosphinyl)-δ-valerolactone 在 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 α(Z)-Propylidene-δ-valerolactone 、 (E)-3-propylidenetetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Stereocontrol in Horner-Wadsworth-Emmons condensations of .alpha.-phosphono lactones with aldehydes: a synthesis of integerrinecic acid and senecic acid lactones

  摘要：

  The Homer-Wadsworth-Emmons condensations of alpha-phosphono lactones were investigated under a variety of conditions. Upon treatment with KHMDS and 18-crown-6 in THF, condensations of the five-membered ring phosphono lactones 7a and 8 with propionaldehyde afforded the E olefins cleanly. In contrast, these phosphonates gave predominantly the Z olefins upon treatment with propionaldehyde, K2CO3, and 18-crown-6 in THF. A similar, though somewhat less-pronounced trend was observed with the six-membered ring phosphono lactone 9a. However, in its condensation with acetaldehyde the more functionalized phosphono lactone 4 gave the best E selectivity (ca. 9:1) when DBU/CH3CN was used, providing the methyl ester of integerrinecic acid lactone (5) in 77% isolated yield. When K2CO3/18-crown-6/toluene was employed in a parallel reaction, only slight selectivity for the Z isomer was observed, but the methyl ester of senecic acid lactone (6) still was obtained in 43-46% yield from the product mixture.

  DOI：

  10.1021/jo00074a023
• 作为产物：
  描述：

  在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.0h， 生成 α-(Diisopropoxyphosphinyl)-δ-valerolactone
  参考文献：
  名称：

  Stereocontrol in Horner-Wadsworth-Emmons condensations of .alpha.-phosphono lactones with aldehydes: a synthesis of integerrinecic acid and senecic acid lactones

  摘要：

  The Homer-Wadsworth-Emmons condensations of alpha-phosphono lactones were investigated under a variety of conditions. Upon treatment with KHMDS and 18-crown-6 in THF, condensations of the five-membered ring phosphono lactones 7a and 8 with propionaldehyde afforded the E olefins cleanly. In contrast, these phosphonates gave predominantly the Z olefins upon treatment with propionaldehyde, K2CO3, and 18-crown-6 in THF. A similar, though somewhat less-pronounced trend was observed with the six-membered ring phosphono lactone 9a. However, in its condensation with acetaldehyde the more functionalized phosphono lactone 4 gave the best E selectivity (ca. 9:1) when DBU/CH3CN was used, providing the methyl ester of integerrinecic acid lactone (5) in 77% isolated yield. When K2CO3/18-crown-6/toluene was employed in a parallel reaction, only slight selectivity for the Z isomer was observed, but the methyl ester of senecic acid lactone (6) still was obtained in 43-46% yield from the product mixture.

  DOI：

  10.1021/jo00074a023

文献信息

• Stereocontrol in Horner-Wadsworth-Emmons condensations of .alpha.-phosphono lactones with aldehydes: a synthesis of integerrinecic acid and senecic acid lactones
  作者：Koo Lee、John A. Jackson、David F. Wiemer

  DOI：10.1021/jo00074a023

  日期：1993.10

  The Homer-Wadsworth-Emmons condensations of alpha-phosphono lactones were investigated under a variety of conditions. Upon treatment with KHMDS and 18-crown-6 in THF, condensations of the five-membered ring phosphono lactones 7a and 8 with propionaldehyde afforded the E olefins cleanly. In contrast, these phosphonates gave predominantly the Z olefins upon treatment with propionaldehyde, K2CO3, and 18-crown-6 in THF. A similar, though somewhat less-pronounced trend was observed with the six-membered ring phosphono lactone 9a. However, in its condensation with acetaldehyde the more functionalized phosphono lactone 4 gave the best E selectivity (ca. 9:1) when DBU/CH3CN was used, providing the methyl ester of integerrinecic acid lactone (5) in 77% isolated yield. When K2CO3/18-crown-6/toluene was employed in a parallel reaction, only slight selectivity for the Z isomer was observed, but the methyl ester of senecic acid lactone (6) still was obtained in 43-46% yield from the product mixture.