Diethyl (1-Formyl-1-phenylmethyl)phosphonate | 33142-26-6

• 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 (1-Formyl-1-phenylmethyl)phosphonate
• 英文别名: phenyl-1 oxo-2 ethylphosphonate de diethyle；diethyl (2-oxo-1-phenyl)ethylphosphonate；diethyl-(2-oxo-1-phenylethyl)phosphonate；diethyl 1-formyl benzyl phosphonate；<2-Oxo-1-phenyl-aethyl>-phosphonsaeurediaethylester；2-Oxo-1-phenylethanphosphonsaeurediethylester；Phenyldiethoxyphosphorylacetaldehyde；2-diethoxyphosphoryl-2-phenylacetaldehyde
• CAS: 33142-26-6
• 化学式: C₁₂H₁₇O₄P
• 分子量: 256.238
• InChiKey: PMZSFJAQLAAPDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Diethyl (1-Formyl-1-phenylmethyl)phosphonate 在 盐酸 、 水 、 potassium hydride 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-(4-bromophenyl)-4-phenyl-1H-pyrazole
  参考文献：
  名称：

  β-Tosylhydrazono Phosphonates in Organic Synthesis. An Unambiguous Entry to Polysubstituted Pyrazoles

  摘要：

  δ-对甲苯磺酰基肼基膦酸盐是一种新型的双功能试剂，用于以芳香族和脂肪族醛为原料，通过一次操作简便地制备出多种多取代吡唑。

  DOI：

  10.1055/s-1999-2608
• 作为产物：
  描述：

  苯基膦酸二乙酯 在 盐酸 作用下， 生成 Diethyl (1-Formyl-1-phenylmethyl)phosphonate
  参考文献：
  名称：

  Grassberger,M.A., Justus Liebigs Annalen der Chemie, 1974, p. 1872 - 1875

  摘要：

  DOI：

文献信息

• A New Synthesis of Vinyl Phosphonates from α-Phenyl β-Oxo Phosphonates and Dialkyl Phosphite
  作者：Young Joo Koh、Dong Young Oh

  DOI：10.1080/00397919508011804

  日期：1995.9

  Abstract Reaction of 1-phenyl 2-oxo phosphonates with dialkyl phosphite sodium salt gave (E) vinyl phosphonates in good yield.

  摘要 1-苯基2-氧代膦酸酯与亚磷酸二烷基酯钠盐反应以良好的收率得到(E)乙烯基膦酸酯。
• METAL(I) AND METAL(II) DERIVATIVES OF DIETHYL (2-OXO-1-PHENYL) ETHYLPHOSPHONATE: SYNTHESIS, STRUCTURE AND REACTIVITY
  作者：Erhard T.K. Haupt、Jordanka Petrova、Zdravka Zdravkova、Nikolay G. Vassilev、Gabriele Eggers

  DOI：10.1080/10426509808033730

  日期：1998.10.1

  Abstract The synthesis and structures of sodium, potassium, calcium and magnesium derivatives of 2-diethoxyphosphonyl-2-phenylethen-1-01 1 (2, 3, 4 and 5 respectively) are described. The alkaline salts 2 and 3 are proven to be pure (E)-enolates, while the alkaline earth metal complexes 4 and 5 are diastereomeric mixtures of (Z) and (E) enolate. forms. The reactivity of the metal derivatives is studied

  摘要 描述了2-diethoxyphosphonyl-2-phenylethen-1-01 1 (分别为2、3、4和5)的钠、钾、钙和镁衍生物的合成和结构。碱性盐 2 和 3 被证明是纯的 (E)-烯醇化物，而碱土金属配合物 4 和 5 是 (Z) 和 (E) 烯醇化物的非对映异构混合物。形式。在酰化、烷基化和羰基烯化反应中研究了金属衍生物的反应性。只有 O-乙酰化 (6) 和 O-苄基化 (7) 产物作为非对映异构体的混合物获得，其中 (E)-烯醇的衍生物形式占主导地位。4与苯甲醛的羰基烯化反应在所选条​​件下不会发生。
• Synthese de phosphonates β-carbonyles
  作者：Elie Elia Aboujaoude、Noel Collignon、Philippe Savignac

  DOI：10.1016/0022-328x(84)85128-1

  日期：1984.3
• Buzykin, B. I.; Sokolov, M. P.; Pavlov, V. A., Journal of general chemistry of the USSR, 1990, vol. 60, # 3, p. 475 - 483
  作者：Buzykin, B. I.、Sokolov, M. P.、Pavlov, V. A.、Ivanova, V. N.、Chertanova, L. F.、Zyablikova, T. A.

  DOI：——

  日期：——
• 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.