| 1393134-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 1393134-20-7
• 化学式: C₇₇H₅NO
• 分子量: 959.893
• InChiKey: BPMKEKGOTVDFDO-NRKKKJJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.64
• 重原子数：
  79.0
• 可旋转键数：
  1.0
• 环数：
  39.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  、 溴甲苯 、 苯甲腈 在 四丁基高氯酸铵 作用下， 反应 3.0h， 以37%的产率得到
  参考文献：
  名称：

  Regioselective Oxazolination of C₇₀^2– and Formation of cis-1 C₇₀ Adduct with Respect to the Apical Pentagon

  摘要：

  Oxazolination of C-70 has been achieved via the aerobic oxidation of C-70(2-) in the presence of PhCN. Only one C-70 oxazoline regioisomer (1) is obtained, indicating that the oxazolination of C-70(2-) occurs with an unusual regioselectivity. Further benzylation of 1(2-) with benzyl bromide leads to the formation of the first cis-1 C-70 derivative with respect to the apical pentagon (2), as shown by the X-ray single-crystal structure and various spectral characterizations. The structure of the obtained C-70 oxazoline (1) is resolved with H/D labeling benzylation and HMBC (heteronuclear multiple bond coherence) NMR on the basis of the structure of 2. The result shows that for compound 1, the O atom is selectively bonded to the C1, while the N atom is bonded to the C2 of C-70. The exhibited regioselectivity for the orientation of oxazolino group on C-70 is further rationalized with computational calculations, and a reaction mechanism for the oxazolination of C-70(2-) is proposed.

  DOI：

  10.1021/jo301017a
• 作为产物：
  描述：

  苯甲腈 、 富勒烯 在 四丁基高氯酸铵 、 碘 作用下， 反应 1.5h， 以6%的产率得到
  参考文献：
  名称：

  Regioselective Oxazolination of C₇₀^2– and Formation of cis-1 C₇₀ Adduct with Respect to the Apical Pentagon

  摘要：

  Oxazolination of C-70 has been achieved via the aerobic oxidation of C-70(2-) in the presence of PhCN. Only one C-70 oxazoline regioisomer (1) is obtained, indicating that the oxazolination of C-70(2-) occurs with an unusual regioselectivity. Further benzylation of 1(2-) with benzyl bromide leads to the formation of the first cis-1 C-70 derivative with respect to the apical pentagon (2), as shown by the X-ray single-crystal structure and various spectral characterizations. The structure of the obtained C-70 oxazoline (1) is resolved with H/D labeling benzylation and HMBC (heteronuclear multiple bond coherence) NMR on the basis of the structure of 2. The result shows that for compound 1, the O atom is selectively bonded to the C1, while the N atom is bonded to the C2 of C-70. The exhibited regioselectivity for the orientation of oxazolino group on C-70 is further rationalized with computational calculations, and a reaction mechanism for the oxazolination of C-70(2-) is proposed.

  DOI：

  10.1021/jo301017a