diethyl (4-[(t-butyldimethyl)silyloxymethyl]phenyl)methylphosphonate | 1137728-04-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl (4-[(t-butyldimethyl)silyloxymethyl]phenyl)methylphosphonate
• 英文别名: Tert-butyl-[[4-(diethoxyphosphorylmethyl)phenyl]methoxy]-dimethylsilane
• CAS: 1137728-04-1
• 化学式: C₁₈H₃₃O₄PSi
• 分子量: 372.517
• InChiKey: HBTICVSAKOCIPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ((diethoxyphosphoryl)methyl)zinc(II) iodide 、 硅烷,(1,1-二甲基乙基)[(4-碘苯基)甲氧基]二甲基- 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 10.08h， 以71%的产率得到diethyl (4-[(t-butyldimethyl)silyloxymethyl]phenyl)methylphosphonate
  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