4-(Diethoxyphosphoryl)-2-methoxy-5-oxo-4-(2-methoxyprop-2-enyl)hept-1-ene | 131904-14-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 4-(Diethoxyphosphoryl)-2-methoxy-5-oxo-4-(2-methoxyprop-2-enyl)hept-1-ene
• CAS: 131904-14-8
• 化学式: C₁₆H₂₉O₆P
• 分子量: 348.376
• InChiKey: LQOOBPPCVAEERW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  23.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-甲氧基-3-溴丙烯 、 二乙基(2-氧丁基)膦 在 potassium tert-butylate 作用下， 生成 钾二乙基磷酸酯 、 4-(Diethoxyphosphoryl)-2-methoxy-5-oxohept-1-ene 、 4-(Diethoxyphosphoryl)-2-methoxy-5-oxo-4-(2-methoxyprop-2-enyl)hept-1-ene
  参考文献：
  名称：

  Methylenomycin B: new syntheses based on .beta.- and .gamma.-keto phosphonates and .gamma.-keto phosphine oxides

  摘要：

  Methylenomycin B has been synthesized from diethyl 2-oxobutanephosphonate (4) in three steps in 39% overall yield. Starting from diethyl 3-oxobutanephosphonate (10) and diphenyl(3-oxobutyl)phosphine oxide (13), methylenomycin B has been obtained in 34% and 27% overall yield, respectively. A characteristic feature of these syntheses of methylenomycin B is that the exo-methylene function is introduced via the Horner-Wittig reaction of formaldehyde (36% aqueous solution) with the corresponding alpha-phosphorylcyclopentenones 6 and 20. The latter were obtained from phosphorylated 1,4-diketones by intramolecular base-catalyzed cyclization. A brief discussion of some mechanistic aspects of the Conant reaction is also given.

  DOI：

  10.1021/jo00003a051