| 1265172-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 1265172-83-5
• 化学式: C₈₁H₁₉NO
• 分子量: 1024.03
• InChiKey: VPEMCBBJSBEMLE-FBCWWBABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.05
• 重原子数：
  83.0
• 可旋转键数：
  5.0
• 环数：
  36.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  、 苄基溴-α,α-d2 、 溴甲苯 以 苯甲腈 为溶剂， 反应 2.05h， 生成 (1R,4R,5R,7S)-4-(hydroxymethyl)-8,8-dimethyl-2-oxo-3-oxabicyclo[5.1.0]octan-5-yl benzoate 、
  参考文献：
  名称：

  Electrochemical and H/D-Labeling Study of Oxazolino[60]Fullerene Rearrangement

  摘要：

  Isomerization of an oxazoline cycle from a [6,6]- to [5,6]-junction on the C(60) sphere of dianionic [60]fullero-oxazoline (1(2-)) during a 1,4-addition is studied by electrochemistry and a stepwise addition of PhCH(2)Br and PhCD(2)Br. Cyclic voltammerty of the in situ generated 1(2-) shows a very unusual positive shift for the anodic peak corresponding to the oxidation of 1(2-), indicating that the C(60) cage of dianionic 1 bears only one unit negative charge due to the heterolytic cleavage of the C(60)-O bond. Further study with a stepwise addition of PhCH(2)Br and PhCD(2)Br, which are used to differentiate the aryl groups added at each step onto dianionic 1, shows explicitly there is an exclusive selectivity of the C-O bond for the ring-opening and ring-closure during the isomerization of the heterocycle. A reaction mechanism is proposed on the basis of the experimental results and computational calculations.

  DOI：

  10.1021/jo1023798