| 158871-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 158871-73-9
• 化学式: C₇₁H₄F₄N₂O₄
• 分子量: 1024.82
• InChiKey: PHKCUJKPYQPXQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  81
• 可旋转键数：
  4
• 环数：
  35.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.7
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  L-谷氨酸二乙酯盐酸盐 、 在 三乙胺 作用下， 以63%的产率得到
  参考文献：
  名称：

  Photochemical and Thermal Reactions of C60 with N-Succinimidyl 4-Azido-2,3,5,6-tetrafluorobenzoate: A New Method for Functionalization of C60

  摘要：

  The first example of a photochemical reaction between C-60 and an N-hydroxysuccinimide (NHS) functionalized perfluorophenyl azide (PFPA) is reported. Photolysis of a chlorobenzene solution of C-60 and N-succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate (1) at 300 nm gave exclusively the monoadduct azamethanofullerene 2 in 10% yield (39% based on recovered C-60) The reaction is believed to take place via the addition of the photogenerated, highly reactive nitrene intermediate to a 6,6 double bond of C-60. The NHS active ester group present in 2 served as a site for attachment of other molecules by way of an acylation reaction. For example, 2 was allowed to react with L-glutamic acid diethyl ester or benzylamine to give the corresponding amides 3 or 4. Thermal reaction of C-60 and 1 in chlorobenzene at 105-108 degrees C gave the same adduct 2 in 25% yield (45% based on recovered C-60).

  DOI：

  10.1021/jo00099a025
• 作为产物：
  描述：

  N-琥珀酰亚胺4-叠氮-2,3,5,6-四氟苯甲酸 、 足球烯 以 氯苯 为溶剂， 反应 120.0h， 以23%的产率得到
  参考文献：
  名称：

  Photochemical and Thermal Reactions of C60 with N-Succinimidyl 4-Azido-2,3,5,6-tetrafluorobenzoate: A New Method for Functionalization of C60

  摘要：

  The first example of a photochemical reaction between C-60 and an N-hydroxysuccinimide (NHS) functionalized perfluorophenyl azide (PFPA) is reported. Photolysis of a chlorobenzene solution of C-60 and N-succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate (1) at 300 nm gave exclusively the monoadduct azamethanofullerene 2 in 10% yield (39% based on recovered C-60) The reaction is believed to take place via the addition of the photogenerated, highly reactive nitrene intermediate to a 6,6 double bond of C-60. The NHS active ester group present in 2 served as a site for attachment of other molecules by way of an acylation reaction. For example, 2 was allowed to react with L-glutamic acid diethyl ester or benzylamine to give the corresponding amides 3 or 4. Thermal reaction of C-60 and 1 in chlorobenzene at 105-108 degrees C gave the same adduct 2 in 25% yield (45% based on recovered C-60).

  DOI：

  10.1021/jo00099a025

文献信息

• Photochemical and Thermal Reactions of C60 with N-Succinimidyl 4-Azido-2,3,5,6-tetrafluorobenzoate: A New Method for Functionalization of C60
  作者：Mingdi Yan、Sui Xiong Cai、John F. W. Keana

  DOI：10.1021/jo00099a025

  日期：1994.10

  The first example of a photochemical reaction between C-60 and an N-hydroxysuccinimide (NHS) functionalized perfluorophenyl azide (PFPA) is reported. Photolysis of a chlorobenzene solution of C-60 and N-succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate (1) at 300 nm gave exclusively the monoadduct azamethanofullerene 2 in 10% yield (39% based on recovered C-60) The reaction is believed to take place via the addition of the photogenerated, highly reactive nitrene intermediate to a 6,6 double bond of C-60. The NHS active ester group present in 2 served as a site for attachment of other molecules by way of an acylation reaction. For example, 2 was allowed to react with L-glutamic acid diethyl ester or benzylamine to give the corresponding amides 3 or 4. Thermal reaction of C-60 and 1 in chlorobenzene at 105-108 degrees C gave the same adduct 2 in 25% yield (45% based on recovered C-60).