3-Methyl-1-(2,6-di-tert-butyl-4-methylphenoxy)-3-phospholene 1-oxide | 151369-27-6

• 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: 3-Methyl-1-(2,6-di-tert-butyl-4-methylphenoxy)-3-phospholene 1-oxide
• 英文别名: 1-(2,6-ditert-butyl-4-methylphenoxy)-3-methyl-2,5-dihydro-1λ5-phosphole 1-oxide
• CAS: 151369-27-6
• 化学式: C₂₀H₃₁O₂P
• 分子量: 334.439
• InChiKey: FNKAGTCZVMNVQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-Methyl-1-(2,6-di-tert-butyl-4-methylphenoxy)-3-phospholene 1-oxide 在 溴 、 三乙胺 作用下， 以 氯仿 、 苯 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Experiments on the generation of 2-coordinate phosphoryl species by fragmentation of 7-phosphanorbornene and 3-phospholene derivatives

  摘要：

  2,6-Di-tert-butyl-4-methylphenylphosphenite (ArOP=O) was released into the gas phase on heating a neat sample of a 7-phosphanorbornene derivative 6 bearing this aryloxy substituent at 300-degrees-C (0.01 mm). Attempts to prepare 1-adamantyl phosphenite similarly were not successful. Irradiation of 6 in 1,2-dichloroethane at 254 nm failed to cause release of the phosphenite, but when some alcohol was present fragmentation proceeded readily to give the H-phosphonate (ArOPH(O)OR). It was deduced that the species undergoing the fragmentation was a 5-coordinate adduct of 6 and the alcohol. Similar behavior was observed for the other esters and also for a P-phenyl oxide and a P-phenyl sulfide in the 7-phosphanorbornene series, as well as for a 3-phospholene oxide. Isotope exchange experiments with (OH2)-O-18 proved the influence of the irradiation on the formation and fragmentation of the 5-coordinate adduct. Earlier literature reports that 2-coordinate species are released on irradiation of 7-phosphanorbornene and 3-phospholene derivatives therefore need reinterpretation.

  DOI：

  10.1021/jo00075a014
• 作为产物：
  描述：

  2,6-二叔丁基-4-甲基苯酚 、 1-chloro-3-methyl-3-phospholene-1-oxide 在 正丁基锂 作用下， 以 苯 为溶剂， 以40%的产率得到3-Methyl-1-(2,6-di-tert-butyl-4-methylphenoxy)-3-phospholene 1-oxide
  参考文献：
  名称：

  Experiments on the generation of 2-coordinate phosphoryl species by fragmentation of 7-phosphanorbornene and 3-phospholene derivatives

  摘要：

  2,6-Di-tert-butyl-4-methylphenylphosphenite (ArOP=O) was released into the gas phase on heating a neat sample of a 7-phosphanorbornene derivative 6 bearing this aryloxy substituent at 300-degrees-C (0.01 mm). Attempts to prepare 1-adamantyl phosphenite similarly were not successful. Irradiation of 6 in 1,2-dichloroethane at 254 nm failed to cause release of the phosphenite, but when some alcohol was present fragmentation proceeded readily to give the H-phosphonate (ArOPH(O)OR). It was deduced that the species undergoing the fragmentation was a 5-coordinate adduct of 6 and the alcohol. Similar behavior was observed for the other esters and also for a P-phenyl oxide and a P-phenyl sulfide in the 7-phosphanorbornene series, as well as for a 3-phospholene oxide. Isotope exchange experiments with (OH2)-O-18 proved the influence of the irradiation on the formation and fragmentation of the 5-coordinate adduct. Earlier literature reports that 2-coordinate species are released on irradiation of 7-phosphanorbornene and 3-phospholene derivatives therefore need reinterpretation.

  DOI：

  10.1021/jo00075a014

文献信息

• Quin Louis D., Jankowski Stefan, Rudzinski Juliusz, Sommese Anthony G., W+, J. Org. Chem, 58 (1993) N 23, S 6212-6216
  作者：Quin Louis D., Jankowski Stefan, Rudzinski Juliusz, Sommese Anthony G., W+

  DOI：——

  日期：——