diethyl 1-benzoyloxy-3-phenyl-2(E)-propenylphosphonate | 185301-51-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl 1-benzoyloxy-3-phenyl-2(E)-propenylphosphonate
• 英文别名: diethyl benzoyloxy-(E)-cinnamylphosphonate；[(E)-1-diethoxyphosphoryl-3-phenylprop-2-enyl] benzoate
• CAS: 185301-51-3
• 化学式: C₂₀H₂₃O₅P
• 分子量: 374.373
• InChiKey: NHTMPWYNPJBWOQ-FOCLMDBBSA-N

物化性质

• 沸点：
  519.7±50.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  diethyl 1-benzoyloxy-3-phenyl-2(E)-propenylphosphonate 在 samarium diiodide 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (1E,3Z)-1-phenylundeca-1,3-diene
  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
• 作为产物：
  描述：

  反式肉桂醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 titanium(IV) isopropylate 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 diethyl 1-benzoyloxy-3-phenyl-2(E)-propenylphosphonate
  参考文献：
  名称：

  Asymmetric dihydroxylation of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix reagents. Effects of 1-acyloxy functional groups on the asymmetric dihydroxylation

  摘要：

  Asymmetric dihydroxylation (AD) of a racemic mixture of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix-alpha or -beta reagents was examined. The kinetic rate of dihydroxylation was highly dependent upon the configuration of the 1-acyloxy functional group as well as the nature of substituents at the 3-position. ?he reaction of a racemic mixture of diethyl (E)-3-phenyl-1-acetyloxy-2-propenylphosphonate with an AD-mix-beta reagent preferentially dihydroxylated the R-enantiomer to leave an unreacted S-enantiomer of high enantiomeric purity. Double diastereoselection of the resolved diethyl 3-phenyl-1-acetyloxy-2(E)-propenylphosphonate in dihydroxylation was also examined. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10342-8

文献信息

• Asymmetric dihydroxylation of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix reagents. Effects of 1-acyloxy functional groups on the asymmetric dihydroxylation
  作者：Tsutomu Yokomatsu、Takehiro Yamagishi、Tomoyuki Sada、Kenji Suemune、Shiroshi Shibuya

  DOI：10.1016/s0040-4020(97)10342-8

  日期：1998.1

  Asymmetric dihydroxylation (AD) of a racemic mixture of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix-alpha or -beta reagents was examined. The kinetic rate of dihydroxylation was highly dependent upon the configuration of the 1-acyloxy functional group as well as the nature of substituents at the 3-position. ?he reaction of a racemic mixture of diethyl (E)-3-phenyl-1-acetyloxy-2-propenylphosphonate with an AD-mix-beta reagent preferentially dihydroxylated the R-enantiomer to leave an unreacted S-enantiomer of high enantiomeric purity. Double diastereoselection of the resolved diethyl 3-phenyl-1-acetyloxy-2(E)-propenylphosphonate in dihydroxylation was also examined. (C) 1997 Elsevier Science Ltd. All rights reserved.
• 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.