1-diphenylmethyl-1,2-dihydro[60]fullerene | 215032-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-diphenylmethyl-1,2-dihydro[60]fullerene
• 英文别名: 9-benzhydryl-1H-(C60-Ih)[5,6]fullerene
• CAS: 215032-28-3
• 化学式: C₇₃H₁₂
• 分子量: 888.898
• InChiKey: XWNBMEVIWMWGFC-UHFFFAOYSA-N

物化性质

• 密度：
  3.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  18.9
• 重原子数：
  73
• 可旋转键数：
  3
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 1-diphenylmethyl-1,2-dihydro[60]fullerene 在 四丁基氢氧化铵 作用下， 以 甲醇 、 苯甲腈 为溶剂， 以29%的产率得到1-(diphenylmethyl)-4-allyl-1,4-dihydro[60]fullerene
  参考文献：
  名称：

  Alkylation of Dihydrofullerenes

  摘要：

  The falleride dianions C-60(2-) and C-70(2-) were generated by deprotonation of the corresponding hydrogenated fallerenes, 1,2-C60H2 and 1,2-C70H2. These anions were prepared in the presence of a variety of alkylating agents, and mono- or dialkylated products were obtained. Alkylation was not successful with sulfonate ester alkylating agents. Deprotonation of monoalkylated compounds, followed by second alkylation. with a different alkylating agent, produced heterodialkylated compounds. The monoalkyated material was invariably the 1,2-isomers, while the dialkylated materials were generally 1,4-isomers, although some 1,2-isomer was observed in the C-70 context. The major product from alkylation of C-70(2-) was the 7,23-isomer 13a, a structure where the alkylation took place near the equator of the fullerene cage, rather than at the more strained carbons near the poles.

  DOI：

  10.1021/jo020216e
• 作为产物：
  描述：

  足球烯 、 二苯基溴甲烷 在 四丁基高氯酸铵 、 三氟乙酸 作用下， 以 邻二氯苯 为溶剂， 反应 3.5h， 以59%的产率得到1-diphenylmethyl-1,2-dihydro[60]fullerene
  参考文献：
  名称：

  电化学生成的[60]富勒烯的二价阴离子与庞大的仲烷基溴的反应

  摘要：

  电化学生成的[60]富勒烯（C 60 2-）的二价阴离子与庞大的仲烷基溴化物的反应表现出不同的反应行为。C 60 2-与二苯基溴甲烷的反应生成1,2-C 60 HR或1,4-C 60 R 2（R = CHPh 2）加合物，而C 60 2-与2-溴丙二酸二乙酯的反应出乎意料地提供了甲基富勒烯C 60  > CR 2（R ＝ CO 2 Et）。已经提出了合理的反应机理来解释观察到的产物的形成。

  DOI：

  10.1016/j.tetlet.2019.03.019

文献信息

• Reactions of photoexcited C60 with weak organic acids. Novel method for the derivatization of fullerenes
  作者：M Fedurco、K Klostermann、U Kirbach、D Scheller、L Dunsch

  DOI：10.1016/s0009-2614(00)00049-x

  日期：2000.3

  Pyrex-filtered irradiation of C-60 solutions in liquid diphenylmethane in the absence of oxygen is shown to result in Ph,CH. radicals, which further react with the electron-deficient C-60 to give Ph2CH-C60Hn (n = 1, 3, 5). The fullerene ground state to C-3(60) transition is suggested to be accompanied by the increase of the fullerene solvation affecting thus the acidity of methylene hydrogens in Ph2CH2 as well as the feasibility of their dissociation. Also, photolysis of C-60 solutions in weakly acidic phenylacetylene is shown to lead to the addition of a varying number of phenylethinyl groups to the fullerene core. (C) 2000 Elsevier Science B.V. All rights reserved.
• Alkylation of Dihydrofullerenes
  作者：Mark S. Meier、Robert G. Bergosh、Megan E. Gallagher、H. Peter Spielmann、Zhongwen Wang

  DOI：10.1021/jo020216e

  日期：2002.8.1

  The falleride dianions C-60(2-) and C-70(2-) were generated by deprotonation of the corresponding hydrogenated fallerenes, 1,2-C60H2 and 1,2-C70H2. These anions were prepared in the presence of a variety of alkylating agents, and mono- or dialkylated products were obtained. Alkylation was not successful with sulfonate ester alkylating agents. Deprotonation of monoalkylated compounds, followed by second alkylation. with a different alkylating agent, produced heterodialkylated compounds. The monoalkyated material was invariably the 1,2-isomers, while the dialkylated materials were generally 1,4-isomers, although some 1,2-isomer was observed in the C-70 context. The major product from alkylation of C-70(2-) was the 7,23-isomer 13a, a structure where the alkylation took place near the equator of the fullerene cage, rather than at the more strained carbons near the poles.
• Reactions of the electrochemically generated dianion of [60]fullerene with bulky secondary alky bromides
  作者：Kai-Qing Liu、Guan-Wu Wang

  DOI：10.1016/j.tetlet.2019.03.019

  日期：2019.4

  Reactions of the electrochemically generated dianion of [60]fullerene (C602−) with bulky secondary alkyl bromides exhibit different reaction behaviors. Reaction of C602− with diphenylbromomethane gives rise to 1,2-C60HR or 1,4-C60R2 (R = CHPh2) adducts, while reaction of C602− with diethyl 2-bromomalonate unexpectedly affords methanofullerene C60 > CR2 (R = CO2Et). Plausible reaction mechanisms have

  电化学生成的[60]富勒烯（C 60 2-）的二价阴离子与庞大的仲烷基溴化物的反应表现出不同的反应行为。C 60 2-与二苯基溴甲烷的反应生成1,2-C 60 HR或1,4-C 60 R 2（R = CHPh 2）加合物，而C 60 2-与2-溴丙二酸二乙酯的反应出乎意料地提供了甲基富勒烯C 60  > CR 2（R ＝ CO 2 Et）。已经提出了合理的反应机理来解释观察到的产物的形成。