<(4-methoxyphenoxy)methyl>diphenylphosphine | 142041-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: <(4-methoxyphenoxy)methyl>diphenylphosphine
• 英文别名: (4-Methoxyphenoxy)methyl-diphenylphosphane
• CAS: 142041-41-6
• 化学式: C₂₀H₁₉O₂P
• 分子量: 322.343
• InChiKey: UEXVOHNWVVEFCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <(4-methoxyphenoxy)methyl>diphenylphosphine 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以98%的产率得到<(4-methoxyphenyl)methyl>diphenylphosphine oxide
  参考文献：
  名称：

  Synthetic studies on furanoheliangolides. Stereocontrolled construction of the oxygen-bridged tricyclic framework

  摘要：

  The heavily functionalized 6,9-epoxycyclodeca[b]furan-11-ones 34 and 37 have been prepared in 13 steps from 4-methyl-2-[(phenylmethoxy)methyl]furan. The key elements of the scheme include a high-pressure Diels-Alder cycloaddition to 1-cyanovinyl acetate, highly regioselective hydroboration, controlled stepwise oxidation to give keto aldehyde 20, and thermal oxy-Cope rearrangement of both 32 and 36b. The prior introduction of a phenylthio substituent provides for the accommodation of different levels of unsaturation at a more advanced stage of furanoheliangolide construction. While the present strategy is developed around a racemic model, the potential for adoption of enantioselective features is immediate. The overall stereocontrolled sequence provides a general and flexible entry into oxygen-bridged frameworks closely related to substructures occurring in many furan-type germacranolides.

  DOI：

  10.1021/jo00042a036
• 作为产物：
  描述：

  1-(氯甲氧基)-4-甲氧基苯 、 二苯基膦 在 双(三甲基硅烷基)氨基钾 作用下， 生成 <(4-methoxyphenoxy)methyl>diphenylphosphine
  参考文献：
  名称：

  Synthetic studies on furanoheliangolides. Stereocontrolled construction of the oxygen-bridged tricyclic framework

  摘要：

  The heavily functionalized 6,9-epoxycyclodeca[b]furan-11-ones 34 and 37 have been prepared in 13 steps from 4-methyl-2-[(phenylmethoxy)methyl]furan. The key elements of the scheme include a high-pressure Diels-Alder cycloaddition to 1-cyanovinyl acetate, highly regioselective hydroboration, controlled stepwise oxidation to give keto aldehyde 20, and thermal oxy-Cope rearrangement of both 32 and 36b. The prior introduction of a phenylthio substituent provides for the accommodation of different levels of unsaturation at a more advanced stage of furanoheliangolide construction. While the present strategy is developed around a racemic model, the potential for adoption of enantioselective features is immediate. The overall stereocontrolled sequence provides a general and flexible entry into oxygen-bridged frameworks closely related to substructures occurring in many furan-type germacranolides.

  DOI：

  10.1021/jo00042a036

文献信息

• Synthetic studies on furanoheliangolides. Stereocontrolled construction of the oxygen-bridged tricyclic framework
  作者：Dearg S. Brown、Leo A. Paquette

  DOI：10.1021/jo00042a036

  日期：1992.7

  The heavily functionalized 6,9-epoxycyclodeca[b]furan-11-ones 34 and 37 have been prepared in 13 steps from 4-methyl-2-[(phenylmethoxy)methyl]furan. The key elements of the scheme include a high-pressure Diels-Alder cycloaddition to 1-cyanovinyl acetate, highly regioselective hydroboration, controlled stepwise oxidation to give keto aldehyde 20, and thermal oxy-Cope rearrangement of both 32 and 36b. The prior introduction of a phenylthio substituent provides for the accommodation of different levels of unsaturation at a more advanced stage of furanoheliangolide construction. While the present strategy is developed around a racemic model, the potential for adoption of enantioselective features is immediate. The overall stereocontrolled sequence provides a general and flexible entry into oxygen-bridged frameworks closely related to substructures occurring in many furan-type germacranolides.