diethyl 1-(benzoyloxy)-3,7-dimethyl-2,6-octadienylphosphonate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diethyl 1-(benzoyloxy)-3,7-dimethyl-2,6-octadienylphosphonate
• 英文别名: [(2E)-1-diethoxyphosphoryl-3,7-dimethylocta-2,6-dienyl] benzoate
• 化学式: C₂₁H₃₁O₅P
• 分子量: 394.448
• InChiKey: MNVSNDBLMVSILN-FBMGVBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲酰膦酸二乙酯 、 柠檬醛 在 三氢化钐 、 二碘甲烷 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 3.0h， 生成 diethyl 1-(benzoyloxy)-3,7-dimethyl-2,6-octadienylphosphonate 、 diethyl 1-(benzoyloxy)-3,7-dimethyl-2,6-octadienylphosphonate
  参考文献：
  名称：

  Three-Component Coupling of Acylphosphonates and Two Carbonyl Compounds Promoted by Low-Valent Samariums:  One-Pot Synthesis of β-Hydroxyphosphonates

  摘要：

  Three-component coupling of acylphosphonates and two carbonyl compounds leading to beta-hydroxyphosphonates has been achieved with low-valent samariums. Thus, acylphosphonates reacted with aldehydes in the presence of semicatalytic amounts of samarium metal or SmI2 to give acyloxy-phosphonates in good yields. The second coupling reaction of the acyloxyphosphonates with aldehydes or ketones promoted by SmI2 afforded beta-hydroxyphosphonates instead of olefins. Moreover, these two reactions could be carried out in one pot.

  DOI：

  10.1021/jo991357s

文献信息

• Three-Component Coupling of Acylphosphonates and Two Carbonyl Compounds Promoted by Low-Valent Samariums:  One-Pot Synthesis of β-Hydroxyphosphonates
  作者：Ken Takaki、Yuichiro Itono、Akihiro Nagafuji、Yoji Naito、Tetsuya Shishido、Katsuomi Takehira、Yoshikazu Makioka、Yuki Taniguchi、Yuzo Fujiwara

  DOI：10.1021/jo991357s

  日期：2000.1.1

  Three-component coupling of acylphosphonates and two carbonyl compounds leading to beta-hydroxyphosphonates has been achieved with low-valent samariums. Thus, acylphosphonates reacted with aldehydes in the presence of semicatalytic amounts of samarium metal or SmI2 to give acyloxy-phosphonates in good yields. The second coupling reaction of the acyloxyphosphonates with aldehydes or ketones promoted by SmI2 afforded beta-hydroxyphosphonates instead of olefins. Moreover, these two reactions could be carried out in one pot.