diethyl 3-(allyloxy)but-1-ynylphosphonate | 1099651-63-4

• 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 3-(allyloxy)but-1-ynylphosphonate
• 英文别名: 1-Diethoxyphosphoryl-3-prop-2-enoxybut-1-yne
• CAS: 1099651-63-4
• 化学式: C₁₁H₁₉O₄P
• 分子量: 246.243
• InChiKey: OGVFWRVVUCZZNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  diethyl 3-(allyloxy)but-1-ynylphosphonate 、 molybdenum hexacarbonyl 在 二甲基亚砜 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以78%的产率得到diethyl 3-methyl-5-oxo-3,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-4-ylphosphonate
  参考文献：
  名称：

  Mo(CO)₆-Mediated Intramolecular Pauson−Khand Reaction of Substituted Diethyl 3-Allyloxy-1-Propynylphosphonates

  摘要：

  Cyclisation of diethyl 3-allyloxy-1-propynylphosphonates with MO(CO)(6) under PK conditions to give 3-substituted-5-oxo-3,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-4-ylphosphonate, 2a-h, in 45-88% isolated yields was done. The R groups are always syn with H-b (where applicable). The stereochemistry was determined via both NMR and crystal X-ray analysis.

  DOI：

  10.1021/jo801988k
• 作为产物：
  描述：

  allyl 1-methylprop-2-ynyl ether 、 氯磷酸二乙酯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 以2.755 g的产率得到diethyl 3-(allyloxy)but-1-ynylphosphonate
  参考文献：
  名称：

  Mo(CO)₆-Mediated Intramolecular Pauson−Khand Reaction of Substituted Diethyl 3-Allyloxy-1-Propynylphosphonates

  摘要：

  Cyclisation of diethyl 3-allyloxy-1-propynylphosphonates with MO(CO)(6) under PK conditions to give 3-substituted-5-oxo-3,5,6,6a-tetrahydro-1H-cyclopenta[c]furan-4-ylphosphonate, 2a-h, in 45-88% isolated yields was done. The R groups are always syn with H-b (where applicable). The stereochemistry was determined via both NMR and crystal X-ray analysis.

  DOI：

  10.1021/jo801988k

文献信息

• Molybdenum-Mediated Deconjugation of α,β-Unsaturated Fused-Cyclopentenone Phosphonates
  作者：Dmitri Gelman、Morris Srebnik†、Dorit Moradov、Abraham Rubinstein

  DOI：10.1055/s-0031-1289751

  日期：2012.4

  The synthesis of diethyl (3-alkyl-5-oxo-4,5,6,6a-tetra­hydro-1H-cyclopenta[c]furan-4-yl)phosphonates from the corresponding 3-allyloxy-1-propynylphosphonates is described. The in situ reaction involves two steps: an intramolecular Pauson-Khand reaction followed by an unusual double bond deconjugation mediated by molybdenum hexacarbonyl in dimethyl sulfoxide.

  描述了由相应的3-烯丙氧基-1-丙炔基膦酸酯合成(3-烷基-5-氧代-4,5,6,6a-四氢-1H-环戊[c]呋喃-4-基)膦酸二乙酯。原位反应涉及两个步骤：分子内 Pauson-Khand 反应，然后是二甲基亚砜中的六羰基钼介导的不寻常的双键解共轭。