diethyl 2-hydroxy-3-oxobutylphosphonate | 138228-78-1

• 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 2-hydroxy-3-oxobutylphosphonate
• 英文别名: 4-Diethoxyphosphoryl-3-hydroxybutan-2-one
• CAS: 138228-78-1
• 化学式: C₈H₁₇O₅P
• 分子量: 224.194
• InChiKey: KBABTJFTJBDTPC-UHFFFAOYSA-N

物化性质

• 沸点：
  338.7±32.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2,2-triethoxy-2,2-dihydro-5-methyl-1,2λ⁵-oxaphospholene 在 盐酸 、 3-苯基-2-甲苯磺酰-1,2-氧杂氮杂环丙烷 作用下， 生成 diethyl 2-hydroxy-3-oxobutylphosphonate
  参考文献：
  名称：

  α,β-functionalization of enones via pentacovalent oxaphospholenes

  摘要：

  2,2,2-Triethoxy-1,2-lambda-5-oxaphospholene, 1, reacts under mild, neutral conditions with bromine, dialkyl azodicarboxylates, and oxaziridines to produce beta-heteroatom substituted gamma-ketophosphonates and beta-acyl vinyl phosphonate in high yields.

  DOI：

  10.1016/s0040-4039(00)92373-6

文献信息

• Synthese von Phosphono�pfels�ureestern durch Reduktion von 3-Phosphonopyruvaten
  作者：R. Neidlein、H. Feistauer

  DOI：10.1007/bf00807637

  日期：1997.1

  The reduction of 3-phosphonopyruvates with ammonia-borane complex proceeds with a very high diastereoselectivity (25:1). Syn- and anti-diastereoisomeric hydroxy esters could be unambiguously assigned by NMR spectroscopy. Furthermore, other beta-ketophosphonates could easily be reduced. Thus, diethyl-3,3-diethoxy-2-hydroxybutyl phosphonate was obtained which gave diethy-2-hydroxy-3-oxobutyl phosphonate after hydrolysis the first known phosphonoacyloine.
• α,β-functionalization of enones via pentacovalent oxaphospholenes
  作者：Cynthia K. McClure、Christopher W. Grote

  DOI：10.1016/s0040-4039(00)92373-6

  日期：1991.9

  2,2,2-Triethoxy-1,2-lambda-5-oxaphospholene, 1, reacts under mild, neutral conditions with bromine, dialkyl azodicarboxylates, and oxaziridines to produce beta-heteroatom substituted gamma-ketophosphonates and beta-acyl vinyl phosphonate in high yields.