Triethyl α-Phosphono-3,3-dimethylbutyrate | 87271-96-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Triethyl α-Phosphono-3,3-dimethylbutyrate
• 英文别名: Ethyl 2-diethoxyphosphoryl-3,3-dimethylbutanoate
• CAS: 87271-96-3
• 化学式: C₁₂H₂₅O₅P
• 分子量: 280.301
• InChiKey: OPYCQQSGENNABB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  Triethyl α-Phosphono-3,3-dimethylbutyrate 、 苯甲醛 在 sodium hydride 作用下， 生成 3,3-Dimethyl-2-[1-phenyl-meth-(Z)-ylidene]-butyric acid ethyl ester
  参考文献：
  名称：

  Synthesis and Wittig-Horner Reactions of 1-(Functionally)Substituted 2,2-Dimethylpropanephosphonic Esters (1-t-Butyl-substituted Phosphonic Esters)

  摘要：

  DOI：

  10.1055/s-1983-30372
• 作为产物：
  描述：

  ethyl 2-diethoxyphosphoryl-3,3-bis(methylsulfanyl)prop-2-enoate 、 甲基锂 在 copper(l) iodide 作用下， 生成 Triethyl α-Phosphono-3,3-dimethylbutyrate
  参考文献：
  名称：

  Synthesis and Wittig-Horner Reactions of 1-(Functionally)Substituted 2,2-Dimethylpropanephosphonic Esters (1-t-Butyl-substituted Phosphonic Esters)

  摘要：

  DOI：

  10.1055/s-1983-30372

文献信息

• Reaction of diethyl phosphorochloridite with enolates: a general method for synthesis of .beta.-keto phosphonates and .alpha.-phosphono esters through carbon-phosphorus bond formation
  作者：Koo Lee、David F. Wiemer

  DOI：10.1021/jo00019a016

  日期：1991.9

  The reaction of ketone enolates with diethyl phosphorochloridite, followed by air oxidation of the immediate reaction products, has proven to be a general and convenient method for preparation of beta-keto phosphonates. Fourteen beta-keto phosphonates have been prepared by this method, in an average yield greater than 60%. This procedure also appears to be applicable to preparation of both alpha-phosphono aldehydes and alpha-phosphono esters. Although special precautions may be necessary to avoid aldol condensation during formation of aldehyde enolates, in two cases it was shown that the resulting enolates react readily with diethyl chlorophosphite. Finally, a set of five ethyl esters was converted to alpha-phosphono esters by this method. Yields of the alpha-phosphono esters are influenced by steric hindrance at the enolate carbon, but the average yield for this series was ca. 70%. Because this synthetic method relies upon an electrophilic phosphorus reagent for formation of the C-P bond, it is complementary to the traditional Arbuzov synthesis. On the basis of the 21 examples presented here, it appears to be more widely applicable.
• SCHAUMANN, E.;FITTKAU, S., SUNTHESIS, BRD, 1983, N 6, 449-450
  作者：SCHAUMANN, E.、FITTKAU, S.

  DOI：——

  日期：——
• Synthesis and Wittig-Horner Reactions of 1-(Functionally)Substituted 2,2-Dimethylpropanephosphonic Esters (1-<i>t</i>-Butyl-substituted Phosphonic Esters)
  作者：Ernst Schaumann、Stefan Fittkau

  DOI：10.1055/s-1983-30372

  日期：——