diethyl 2-[3-(methoxycarbonyl)phenyl]ethylphosphonate | 1137728-00-7

• 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 2-[3-(methoxycarbonyl)phenyl]ethylphosphonate
• 英文别名: Methyl 3-(2-diethoxyphosphorylethyl)benzoate
• CAS: 1137728-00-7
• 化学式: C₁₄H₂₁O₅P
• 分子量: 300.292
• InChiKey: FVBWQRRBBXIUTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  diethyl (2-iodoethyl)phosphonate 、 3-methoxycarbonylphenylzinc iodide 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,1'-bis(diphenylphosphino)ferrocene 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以61%的产率得到diethyl 2-[3-(methoxycarbonyl)phenyl]ethylphosphonate
  参考文献：
  名称：

  Rh-Catalyzed Negishi Alkyl-Aryl Cross-Coupling Leading to α- or β-Phosphoryl-Substituted Alkylarenes

  摘要：

  The catalytic cross-coupling between ArZnX and ICH2(CH2)(n)P(O)(OEt)(2) (n = 0-3) has been investigated to determine the utility of the Rh catalyst during the alkyl-aryl cross-coupling and to develop a new synthetic method for phosphoryl-substituted alkylarenes. Rh-dppf exhibits an excellent catalytic activity for the reaction with the alkylphosphonate of n = 1, whereas for the reaction with those of n = 2 or 3, P-hydride elimination mainly takes place. As for the reaction with an alkylphosphonate of n = 0, a polarity inversion of the coupling components is necessary in order to provide the coupling products; the phosphoryl analogue of the Reformatsky reagent and ArI give the cross-coupling products in good yields through the catalysis by Rh-dppf.

  DOI：

  10.1021/jo900142b

文献信息

• Rh-Catalyzed Negishi Alkyl-Aryl Cross-Coupling Leading to α- or β-Phosphoryl-Substituted Alkylarenes
  作者：Hideki Takahashi、Shinya Inagaki、Naoko Yoshii、Fuxing Gao、Yasushi Nishihara、Kentaro Takagi

  DOI：10.1021/jo900142b

  日期：2009.4.3

  The catalytic cross-coupling between ArZnX and ICH2(CH2)(n)P(O)(OEt)(2) (n = 0-3) has been investigated to determine the utility of the Rh catalyst during the alkyl-aryl cross-coupling and to develop a new synthetic method for phosphoryl-substituted alkylarenes. Rh-dppf exhibits an excellent catalytic activity for the reaction with the alkylphosphonate of n = 1, whereas for the reaction with those of n = 2 or 3, P-hydride elimination mainly takes place. As for the reaction with an alkylphosphonate of n = 0, a polarity inversion of the coupling components is necessary in order to provide the coupling products; the phosphoryl analogue of the Reformatsky reagent and ArI give the cross-coupling products in good yields through the catalysis by Rh-dppf.