3,6-diphenyl-4,5-dimethyl-1-phospha-2-oxanorborn-5-ene

• 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: 3,6-diphenyl-4,5-dimethyl-1-phospha-2-oxanorborn-5-ene
• 英文别名: 4,5-Dimethyl-3,6-diphenyl-2-oxa-1-phosphabicyclo[2.2.1]hept-5-ene
• 化学式: C₁₉H₁₉OP
• 分子量: 294.333
• InChiKey: BBCYCKXMKUONCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,6-diphenyl-4,5-dimethyl-1-phospha-2-oxanorborn-5-ene 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 Potassium;3,4-dimethyl-2-phenyl-1-phosphanidacyclopenta-2,4-diene
  参考文献：
  名称：

  Hetero-Diels−Alder Reactions of 2H-Phospholes with Aldehydes

  摘要：

  Transient 2-phenyl-3,4-dimethyl-5H-phosphole reacts at 150 degreesC with aldehydes RCH=O to give the corresponding [4 + 2] P-O cycloadducts with endo- (major) and exo-R-substituents. The cycloaddition with alpha,beta-unsaturated aldehydes takes place both at the C=O (major) and C=C bonds. Upon heating under reduced pressure, the benzaldehyde cycloadduct dissociates to give back the 2H-phosphole, which either dimerizes, is trapped by diphenylacetylene, or is deprotonated by (BuOK)-Bu-t.

  DOI：

  10.1021/jo020720j

文献信息

• Hetero-Diels−Alder Reactions of 2<i>H</i>-Phospholes with Aldehydes
  作者：Patrick Toullec、Louis Ricard、François Mathey

  DOI：10.1021/jo020720j

  日期：2003.4.1

  Transient 2-phenyl-3,4-dimethyl-5H-phosphole reacts at 150 degreesC with aldehydes RCH=O to give the corresponding [4 + 2] P-O cycloadducts with endo- (major) and exo-R-substituents. The cycloaddition with alpha,beta-unsaturated aldehydes takes place both at the C=O (major) and C=C bonds. Upon heating under reduced pressure, the benzaldehyde cycloadduct dissociates to give back the 2H-phosphole, which either dimerizes, is trapped by diphenylacetylene, or is deprotonated by (BuOK)-Bu-t.