1'-cyano-1,2-methano[60]fullerene

• 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'-cyano-1,2-methano[60]fullerene
• 化学式: C₆₂HN
• 分子量: 759.697
• InChiKey: MDXFIPKFMYOGKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  63
• 可旋转键数：
  0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二溴乙腈 、 足球烯 以 甲苯 、 乙腈 为溶剂， 以30%的产率得到1'-cyano-1,2-methano[60]fullerene
  参考文献：
  名称：

  A new route for the selective synthesis of [6,6]-methanofullerenes. Electrosynthesis of C61HCMe3 and C61HCN

  摘要：

  本文介绍了一种利用 C60 二价离子与二碘或二溴试剂之间的反应来选择性合成甲撑富勒烯的快速而简单的新方法。

  DOI：

  10.1039/cc9960001547

文献信息

• Kinetics and regioselectivity in the Diels–Alder reaction of fulleroids vs. methanofullerene and C60
  作者：Naohiko Ikuma、Yasunori Susami、Takumi Oshima

  DOI：10.1039/b918005b

  日期：——

  from the 1,3-dipolar cycloaddition of fullerene with a diazoalkane, have a [5,6]-open methylene bridge and two highly twisted bridgehead double bonds. The [H,H]- and [H,CN]-substituted fulleroids were found to display significantly enhanced and regioselective Diels–Alder addition as compared with the [6,6] closed methanofullerene and C60 with 2,3-dimethyl-1,3-butadiene, but reduced and nonregioselective

  从富勒烯与重氮烷的1,3-偶极环加成反应获得的富勒烯具有[5,6]-开放的亚甲基桥和两个高度扭曲的桥头双键。这 [高，低与[6,6]封闭的相比，发现]-和[H，CN]取代的富勒化合物显示出显着增强的和区域选择性的Diels–Alder添加 甲基富勒烯和C 60与2,3-二甲基-1,3-丁二烯，但减少且非区域选择性加成 环戊二烯。1：1加合物的NMR分析和量子计算表明，高反应性和区域选择性加成是由于桥头双键处的π轨道未对准。
• Synthesis and characterisation of the methanofullerenes, C60(CHCN) and C60(CBr2)
  作者：Ana M. Benito、Adam D. Darwish、Harold W. Kroto、Mohammed F. Meidine、Roger Taylor、David R.M. Walton

  DOI：10.1016/0040-4039(95)02256-2

  日期：1996.2

  Two new methanofullerenes, C60(CHCN) and C60(CBr2), have been prepared by treating a mixture of [60]fullerene and either CH2BrCN or CHBr3 respectively with LDA. The products were purified by silica gel column chromatography, characterised by EI-MS and IR, and shown by 13C NMR to consist solely of 6-6 ring junction adducts.

  通过分别用LDA处理[60]富勒烯与CH 2 BrCN或CHBr 3的混合物，制备了两种新的亚甲基富勒烯C 60（CHCN）和C 60（CBr 2）。产物通过硅胶柱色谱法纯化，通过EI-MS和IR表征，并通过13 C NMR显示仅由6-6个环结加合物组成。
• Quantitative Spectroscopic Studies of the Photoexcited State Properties of Methano- and Pyrrolidino-[60]fullerene Derivatives
  作者：Bin Ma、Christopher E. Bunker、Radhakishan Guduru、Xian-Fu Zhang、Ya-Ping Sun

  DOI：10.1021/jp971067k

  日期：1997.7.1

  UV/vis absorption and fluorescence spectra and fluorescence quantum yields and lifetimes of a series of methano- and pyrrolidino-[60]fullerene derivatives in different solvents are studied systematically. The absorption and fluorescence properties of the derivatives with different substituents are somewhat different from those of [60]fullerene, but very similar among themselves, indicating that the low-lying transitions and the photoexcited state processes are dictated by the electronic structures of functionalized [60]fullerene cages. The results also allow an examination of the issue concerning discrepancies between experimentally determined transition probabilities and those calculated in terms of the Strickler-Berg equation for fullerene molecules. In addition, quenchings of the excited singlet states of the [60]fullerene derivatives by electron donor N,N-diethylaniline (DEA) and the formation of emissive fullerene-DEA exciplexes in solvents of different polarities are investigated.