allyl-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester | 173781-44-7

• 分子结构分类: 有机化合物 - 有机磷化合物
• 英文名称: allyl-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester
• 英文别名: (1,1-diethoxy-ethyl)-allyl-phosphinic acid ethyl ester；3-[1,1-Diethoxyethyl(ethoxy)phosphoryl]prop-1-ene
• CAS: 173781-44-7
• 化学式: C₁₁H₂₃O₄P
• 分子量: 250.275
• InChiKey: FHEJXKRZUZFYJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  allyl-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester 在 三甲基氯硅烷 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 ethyl allylphosphinate
  参考文献：
  名称：

  1,1-Diethoxyethylphosphinates and phosphonites. Intermediates for the synthesis of functional phosphorus acids

  摘要：

  Masked hypophosphorous and methanephosphonous acid synthons have been developed which provide functional phosphonous esters after mild deprotection.

  DOI：

  10.1016/0040-4039(95)01992-q
• 作为产物：
  描述：

  3-溴丙烯 、 ethyl (1,1-diethoxyethyl)phosphinate 在 sodium 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以80%的产率得到allyl-(1,1-diethoxy-ethyl)-phosphinic acid ethyl ester
  参考文献：
  名称：

  1,1-Diethoxyethylphosphinates and phosphonites. Intermediates for the synthesis of functional phosphorus acids

  摘要：

  Masked hypophosphorous and methanephosphonous acid synthons have been developed which provide functional phosphonous esters after mild deprotection.

  DOI：

  10.1016/0040-4039(95)01992-q

文献信息

• Temporary Protection of<i>H</i>-Phosphinic Acids as a Synthetic Strategy
  作者：Laëtitia Coudray、Jean-Luc Montchamp

  DOI：10.1002/ejoc.200900694

  日期：2009.9

  H-Phosphinates obtained through various methodologies are protected directly via reaction with triethyl orthoacetate. The resulting products can be manipulated easily, and various synthetic reactions are presented. For example, application to the synthesis of aspartate transcarbamoylase (ATCase) or kynureninase inhibitors are illustrated. Other reactions, such as Sharpless' asymmetric dihydroxylation

  通过各种方法获得的H-膦酸酯可通过与原乙酸三乙酯反应直接得到保护。所得产物易于操作，并提出了各种合成反应。例如，举例说明了在天冬氨酸转氨甲酰酶（ATCase）或犬尿氨酸酶抑制剂的合成中的应用。还展示了其他反应，例如Sharpless的不对称二羟基化反应或Grubbs的烯烃交叉复分解反应。
• Alkylation of <i>H</i>-Phosphinate Esters under Basic Conditions
  作者：Isabelle Abrunhosa-Thomas、Claire E. Sellers、Jean-Luc Montchamp

  DOI：10.1021/jo062436o

  日期：2007.4.1

  An efficient and general procedure was developed for the direct alkylation of H-phosphinate esters with LHMDS at low temperature. The simplicity of the reaction allows the use of various H-phosphinate esters and takes place with a wide range of electrophiles. The approach can be employed to access some GABA analogues or precursors to GABA analogues. The isolated yields are moderate to good. This is the first report of an alkylation with a secondary iodide or a primary chloride.