Diethyl 2,4-dioxo-4-ethoxy-3-(triphenylphosphoranylidene)butanephosphonate | 78980-76-4

• 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 2,4-dioxo-4-ethoxy-3-(triphenylphosphoranylidene)butanephosphonate
• 英文别名: ethyl 4-diethoxyphosphoryl-3-oxo-2-(triphenyl-λ5-phosphanylidene)butanoate
• CAS: 78980-76-4
• 化学式: C₂₈H₃₂O₆P₂
• 分子量: 526.506
• InChiKey: QVCVMVHWGJANRC-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135 °C(Solvent: Ethyl acetate; Hexane)
• 沸点：
  640.1±57.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Diethyl 2,4-dioxo-4-ethoxy-3-(triphenylphosphoranylidene)butanephosphonate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 1.17h， 生成 ethyl 3-(trans-2-phenylcyclopropyl)3-oxo-2-(triphenylphosphoranylidene)propanoate
  参考文献：
  名称：

  Cyclopropane derivatives through charge-directed conjugate addition reactions of unsaturated acylphosphoranes

  摘要：

  DOI：

  10.1021/jo00355a039
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 在 盐酸 、 氢氧化钾 、 草酰氯 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 40.5h， 生成 Diethyl 2,4-dioxo-4-ethoxy-3-(triphenylphosphoranylidene)butanephosphonate
  参考文献：
  名称：

  Cooke, Manning P.; Biciunas, Kestutis P., Synthesis, 1981, # 4, p. 283 - 285

  摘要：

  DOI：

文献信息

• Oxidation of acylphosphoranes with sodium hypochlorite. Substituted carboxylic acids through charge-directed conjugate addition reactions
  作者：Manning P. Cooke

  DOI：10.1021/jo00153a027

  日期：1983.3
• Stereochemistry of metal-halogen exchange-initiated intramolecular conjugate addition reactions in the construction of 5-membered carbocycles
  作者：Manning P. Cooke

  DOI：10.1021/jo00031a031

  日期：1992.2

  The stereochemistry of some lithium-iodine exchange-initiated cyclization reactions of model omega-iodo, gamma-substituted activated olefins has been studied. The stereoselectivities of these anionic cyclization reactions have been found to be a function of the olefin activator employed, reaction conditions, Michael acceptor olefin geometry, the nature of the gamma-substituent, and, in some cases, the presence of additives. Cyclization reactions of iodides possessing E olefin geometry give a moderate preference for trans cyclopentane formation while Z olefin geometry leads to extremely high (> 300:1) trans product selectivity. Cyclization reactions of E olefins under radical conditions were found to be slightly more trans-selective than those observed under anionic conditions although Z olefin geometry again promotes very high trans product selectivity. The presence of the allylic methoxyl group in (E)-7d leads to cis selectivity under both anionic and radical conditions. Intramolecular complexation involving the reactive carbon center and the methoxyl group is suggested in both modes as a possible explanation for this cis product selectivity.
• Cooke, Manning P.; Widener, Rexford K., Journal of Organic Chemistry, 1987, vol. 52, # 8, p. 1382 - 1396
  作者：Cooke, Manning P.、Widener, Rexford K.

  DOI：——

  日期：——
• COOKE M. P.; BICIUNAS K. P., SYNTHESIS, 1981, NO 4, 283-285
  作者：COOKE M. P.、 BICIUNAS K. P.

  DOI：——

  日期：——
• COOKE, M. P. ,, JR, J. ORG. CHEM., 1983, 48, N 5, 744-746
  作者：COOKE, M. P. ,, JR

  DOI：——

  日期：——