3-[1,1']Binaphthalenyl-2-yl-3,3-di-tert-butyl-3λ⁵-dioxaphosphirane | 915299-95-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[1,1']Binaphthalenyl-2-yl-3,3-di-tert-butyl-3λ⁵-dioxaphosphirane
• 英文别名: 3,3-Ditert-butyl-3-(1-naphthalen-1-ylnaphthalen-2-yl)-1,2,3lambda5-dioxaphosphirane；3,3-ditert-butyl-3-(1-naphthalen-1-ylnaphthalen-2-yl)-1,2,3λ5-dioxaphosphirane
• CAS: 915299-95-5
• 化学式: C₂₈H₃₁O₂P
• 分子量: 430.527
• InChiKey: VOXZMSYOXICJKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  25.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[1,1']Binaphthalenyl-2-yl-3,3-di-tert-butyl-3λ⁵-dioxaphosphirane 以 氘代甲苯 、 甲苯 为溶剂， 反应 48.0h， 生成 2'-(Di-tert-butyl-phosphinoyl)-[1,1']binaphthalenyl-2-ol
  参考文献：
  名称：

  Intramolecular Arene Epoxidation by Phosphadioxiranes

  摘要：

  Singlet oxygen reacts with binaphthyl phosphine derivatives such as 1,1'-binaphthyl di-tert-butyl phosphine to form the corresponding binaphthyl-2-oxide phosphine oxides. This new intramolecular arene epoxidation reaction proceeds with complete retention of stereochemistry. The binaphthyl-2-oxide di-tert-butyl phosphine oxide undergoes a slow "NIH-rearrangement" to form the corresponding hydroxylated product. A transient phosphadioxirane intermediate has been directly observed by low-temperature NMR. Kinetic analyses show that all of the phosphadioxirane intermediate is converted to product.

  DOI：

  10.1021/ol0622007
• 作为产物：
  描述：

  racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl 在 氧气 、 tetraphenylporphyrin 作用下， 以 氘代甲苯 为溶剂， 生成 1,1'-binaphthyl-diptert-butylphosphine oxide 、 3-[1,1']Binaphthalenyl-2-yl-3,3-di-tert-butyl-3λ⁵-dioxaphosphirane
  参考文献：
  名称：

  Intramolecular Arene Epoxidation by Phosphadioxiranes

  摘要：

  Singlet oxygen reacts with binaphthyl phosphine derivatives such as 1,1'-binaphthyl di-tert-butyl phosphine to form the corresponding binaphthyl-2-oxide phosphine oxides. This new intramolecular arene epoxidation reaction proceeds with complete retention of stereochemistry. The binaphthyl-2-oxide di-tert-butyl phosphine oxide undergoes a slow "NIH-rearrangement" to form the corresponding hydroxylated product. A transient phosphadioxirane intermediate has been directly observed by low-temperature NMR. Kinetic analyses show that all of the phosphadioxirane intermediate is converted to product.

  DOI：

  10.1021/ol0622007

文献信息

• Intramolecular Arene Epoxidation by Phosphadioxiranes
  作者：Dong Zhang、Ruomei Gao、Shabana Afzal、Mario Vargas、Shantanu Sharma、Alison McCurdy、Muhammed Yousufuddin、Timothy Stewart、Robert Bau、Matthias Selke

  DOI：10.1021/ol0622007

  日期：2006.10.1

  Singlet oxygen reacts with binaphthyl phosphine derivatives such as 1,1'-binaphthyl di-tert-butyl phosphine to form the corresponding binaphthyl-2-oxide phosphine oxides. This new intramolecular arene epoxidation reaction proceeds with complete retention of stereochemistry. The binaphthyl-2-oxide di-tert-butyl phosphine oxide undergoes a slow "NIH-rearrangement" to form the corresponding hydroxylated product. A transient phosphadioxirane intermediate has been directly observed by low-temperature NMR. Kinetic analyses show that all of the phosphadioxirane intermediate is converted to product.