1,2-{[1',4']epicyclopent-2'-eno}-[60]fullerene | 148035-17-0

• 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: 1,2-{[1',4']epicyclopent-2'-eno}-[60]fullerene
• CAS: 148035-17-0
• 化学式: C₆₅H₆
• 分子量: 786.763
• InChiKey: PUNMZZVKACGTKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.5
• 重原子数：
  65.0
• 可旋转键数：
  0.0
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,2-{[1',4']epicyclopent-2'-eno}-[60]fullerene 、 4-甲基-1,2,4-三吖啉-3,5-二酮 以 1,1,2,2-四氯乙烷 为溶剂， 反应 4.0h， 以30%的产率得到4'-methyl-3',5'-dioxo-1',2',4'-triazabicyclo[3.2.0]heptano-[6',7':1,2]-endonorborneno-[6'',7'':3,4]-1,2,3,4,-tetrahydro-[60]fullerene
  参考文献：
  名称：

  通过 4-甲基-1,2,4-三唑啉-3,5-二酮的光化学环加成对 [60] 富勒烯和 [60] 富勒烯单加合物的官能化

  摘要：

  已经研究了 4-甲基-1,2,4-三唑啉-3,5-二酮 (NMTAD) 与 C60 和几种富勒烯衍生物的光反应。通常，NMTAD 环加成到 C60 及其具有封闭结构的单加合物以高度区域选择性的 [2+2] 方式在 cis-1 [6,6] 双键上。氮杂富勒烯的环加成通过稍微不同的途径发生，并导致部分簇开双（加合物）。然而，1,6-Methano[60] 富勒烯在没有光的情况下也会发生 [2+2+2] 环加成反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300297
• 作为产物：
  描述：

  环戊二烯 、 足球烯 以 苯 为溶剂， 以74%的产率得到1,2-{[1',4']epicyclopent-2'-eno}-[60]fullerene
  参考文献：
  名称：

  从火焰中分离富勒烯产物：C 60-环戊二烯加合物的结构和合成

  摘要：

  从低压苯火焰中分离出AC 60 -C 5 H 6加合物。该产物的结构与C 60和环戊二烯的狄尔斯-阿尔德加合物通过独立合成所确定的相同。经测定，该产物为加合物1至13 C和质子NMR，以及红外和质谱。

  DOI：

  10.1016/0040-4039(93)85006-i

文献信息

• The Diels–Alder reaction of C60 and cyclopentadiene in mesoporous silica as a reaction medium
  作者：Satoshi Minakata、Toshiki Nagamachi、Kazuhisa Nakayama、Takeyuki Suzuki、Takanori Tanaka

  DOI：10.1039/c1cc11437a

  日期：——

  As a new organic reaction medium, a periodic mesoporous inorganic material was found to function as a “solid solvent” in a Diels–Alder reaction of C60 with cyclopentadiene. This finding was supported by a concentration effect and a kinetic study of the reaction.

  作为一种新的有机反应介质，周期性介孔无机材料被发现在C60与环戊二烯的狄尔斯-阿尔德反应中充当“固体溶剂”。这一发现得到了浓度效应和反应动力学研究的支持。
• Reactions of fullerenes C60 and C70 with cyclopentadiene
  作者：Louis S. K. Pang、Michael A. Wilson

  DOI：10.1021/j100128a001

  日期：1993.7

  The kinetics of addition of cyclopentadiene to fullerene C60 and fullerene C70 have been studied in the temperature range 291-354 K by high-pressure liquid chromatography. The rate of addition of cyclopentadiene to fullerene C60 is about 7 times as fast as the rate of addition to fullerene C70 at 293 K. The activation energies for the two reactions are 29 and 67 kJ mol-1, respectively, and reflect the increased electron density in bonds adjoined to two hexagonal rings (C6-C6 bonds) in C60 relative to C70. The log A frequency factor for the reaction of C70 with cyclopentadiene is over twice that for C60 because of the presence of a greater proportion of C6-C6 bonds.
• [4+2+] Diels-Alder Cycloaddition to C60 and C70 Radical Cations in the Gas Phase: A Comparison with Solution
  作者：Hansjuergen Becker、Gholamreza Javahery、Simon Petrie、Diethard K. Bohme

  DOI：10.1021/j100073a002

  日期：1994.6

  Results of an experimental study using the selected-ion flow tube (SIFT) technique are reported for ion-molecule reactions of C-60(.+) With a variety of cycloalkenes and acyclic and cyclic dienes at 294 +/- 2 K in helium gas at a pressure of 0.35 +/- 0.01 Torr. Addition is observed only with 1,3-cyclopentadiene and 1,3-cyclohexadiene. Rate coefficients were measured to be 1.0 and 1.5 x 10(-11) cm(3) molecule(-1) s(-1), respectively. No reactions, k < 3 x 10(-12) cm(3) molecule(-1) s(-1), were observed with 1,3-butadiene, isoprene, 1,3-pentadiene, cyclopentene, cyclohexene, furan, and 1,4-cyclohexadiene. These results provide indirect evidence for the occurrence of a Diels-Alder cycloaddition with 1,3-cyclopentadiene and 1,3-cyclohexadiene. The addition reactions of these two molecules with C-60(.+) were found to be 5 +/- 1 and 6 +/- 2, respectively, faster than the addition reactions with C-70(.+) for which rate coefficients of 2.0 and 2.5 X 10(-12) cm(3) molecule(-1) s(-1), respectively, were measured. This relative reactivity, which in the case of 1,3-cyclopentadiene is remarkably similar to a reported relative reactivity of 7:1 measured in toluene solution at 293 K, has been interpreted in terms of the hybridization of the C atoms in C-60 and C-70.