1,2-(3'-chloroformylcyclopropano)[60]fullerene | 188175-32-8

• 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-(3'-chloroformylcyclopropano)[60]fullerene
• 英文别名: [60]fullerenoacetyl chloride
• CAS: 188175-32-8
• 化学式: C₆₂HClO
• 分子量: 797.142
• InChiKey: FTAUVCDPSVMOHC-UHFFFAOYSA-N

物化性质

• 密度：
  3.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  64
• 可旋转键数：
  1
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-(3'-chloroformylcyclopropano)[60]fullerene 在 18-冠醚-6 sodium azide 、 溴苯 、 三甲基甲硅烷基锡 作用下， 反应 0.3h， 以34%的产率得到azidomethylmethano[60]fullerene
  参考文献：
  名称：

  第一次在甲醇桥碳上合成带有给电子基团的甲烷[60]富勒烯：氨基甲烷[60]富勒烯的合成和反应。

  摘要：

  [反应：参见正文]以叠氮基羰基甲基[60]富勒烯的库尔修斯重排为关键反应，首次合成了氨基甲烷[60]富勒烯为三氟甲磺酸盐。发现由此获得的氨基甲基[60]富勒烯能够与各种酰氯反应以提供相应的酰胺。

  DOI：

  10.1021/ol052509a
• 作为产物：
  描述：

  (1,2-甲桥富勒烯C60)-61-羧酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 5.0h， 以100%的产率得到1,2-(3'-chloroformylcyclopropano)[60]fullerene
  参考文献：
  名称：

  [60]富勒烯乙酰氯作为富勒烯衍生物的多用途前体：与各种醇类形成有效的酯。

  摘要：

  [反应：参见文章] [60]富勒烯基乙酰氯，[60]富勒烯乙酸的反应性衍生物之一，是首次分离和鉴定。该酰氯很容易以高收率由[60]富勒烯乙酸叔丁酯分两步合成。在4-（二甲基氨基）吡啶作为碱的存在下，酰氯在温和条件下与各种醇平稳反应，以中等至高收率得到相应的酯，包括[60]富勒烯-生物分子杂化物。

  DOI：

  10.1021/ol034793g

文献信息

• Synthesis and Reactions of 2,2-[60]Fullerenoalkanoyl Chlorides
  作者：Tomoyuki Tada、Yasuhiro Ishida、Kazuhiko Saigo

  DOI：10.1021/jo052399l

  日期：2006.2.1

  2,2-[60]Fullerenoalkanoyl chlorides (1a−d) were easily and securely prepared from the corresponding 2,2-[60]fullerenoalkanoic acids (2a−d) by the reaction with thionyl chloride in an unusual mixed solvent, CH2Cl2/dioxane. The characterization of 1a−d by 1H and 13C NMR, FT-IR, and MALDI-TOF-MASS was conducted for the first time. The 2,2-[60]fullerenoalkanoyl chlorides thus obtained were readily converted

  通过在不寻常的混合溶剂CH 2中与亚硫酰氯反应，由相应的2，2- [60]富勒烯链烷酸（2a - d）轻松安全地制备2,2- [60]富勒烯链烷酰氯（1a - d）。Cl 2 /二恶烷。用1 H和13表征1a - d首次进行13 C NMR，FT-IR和MALDI-TOF-MASS。通过分别与胺和醇缩合，由此获得的2，2- [60]富勒烯链烷酰氯易于以中等至优异的产率转化为相应的酰胺和酯。进行缩合反应后，可以轻松制备[60]富勒烯-生物分子杂化物。
• Supramolecular Nano Networks Formed by Molecular-Recognition-Directed Self-Assembly of Ditopic Calix[5]arene and Dumbbell [60]Fullerene
  作者：Takeharu Haino、Youko Matsumoto、Yoshimasa Fukazawa

  DOI：10.1021/ja0524088

  日期：2005.6.1

  Dumbbell fullerene 1 and ditopic bisdouble-calix[5]arene 2 were synthesized. Their iterative host-guest complexations create the supramolecular nano network. Scanning electron microscopy revealed the formation of the branched fiber, possessing a length of more than 100 mum and widths of 250-500 nm on a glass plate. More detailed information was given by atomic force microscopy. The formed fibers on

  合成了哑铃富勒烯1和双位双双杯[5]芳烃2。他们的迭代主客体复合创造了超分子纳米网络。扫描电子显微镜显示分枝纤维的形成，在玻璃板上具有超过 100 毫米的长度和 250-500 纳米的宽度。原子力显微镜提供了更详细的信息。在云母板上形成的纤维具有60-90nm的宽度和1.2-1.9nm的高度。纳米尺寸的组件可能由一束 40-60 条聚合物链组成，这些聚合物链通过将烷基侧链与范德华相互作用缠结而成。
• Synthesis of 2,2-[60]Fullerenoalkylamines via the Curtius Rearrangement
  作者：Yasuhiro Ishida、Kazuhiko Saigo、Tomoyuki Tada

  DOI：10.1055/s-2007-968017

  日期：2007.2

  2,2-[60]Fullerenoalkylamines were easily and securely prepared from 2,2-[60]fullerenoalkanoyl azides, which were simply obtained from the corresponding 2,2-[60]fullerenoalkanoyl chlorides through the Curtius rearrangement in the presence of tert-butyl alcohol, followed by debutylation and decarboxylation under acidic conditions.

  2,2-[60] 富勒烯烷基胺很容易和安全地由 2,2-[60] 富勒烯烷酰基叠氮化物制备，这些叠氮化物可以简单地从相应的 2,2-[60] 富勒烯烷酰氯在叔-存在下通过 Curtius 重排获得。丁醇，然后在酸性条件下进行脱丁和脱羧。
• Toward Controlled Spacing in One-Dimensional Molecular Chains:  Alkyl-Chain-Functionalized Fullerenes in Carbon Nanotubes
  作者：Thomas W. Chamberlain、Andrew Camenisch、Neil R. Champness、G. Andrew D. Briggs、Simon C. Benjamin、Arzhang Ardavan、Andrei N. Khlobystov

  DOI：10.1021/ja071803q

  日期：2007.7.1

  A range of fullerenes (C-60) functionalized with long alkyl chains have been synthesized and inserted into single-walled carbon nanotubes. The impact of the alkyl chain length and of the type of linker between the addend and the fullerene cage on the geometry of molecular arrays in nanotube has been studied by high-resolution transmission electron microscopy. In the presence of functional groups the mean interfullerene separations are significantly increased by 2-8 nm depending on the length of the alkyl chain, but the periodicity of the fullerene arrays is disrupted due to the conformational flexibility of the alkyl groups.
• Conformational Analysis of Single Perfluoroalkyl Chains by Single-Molecule Real-Time Transmission Electron Microscopic Imaging
  作者：Koji Harano、Shinya Takenaga、Satoshi Okada、Yoshiko Niimi、Naohiko Yoshikai、Hiroyuki Isobe、Kazu Suenaga、Hiromichi Kataura、Masanori Koshino、Eiichi Nakamura

  DOI：10.1021/ja411235x

  日期：2014.1.8

  Whereas a statistical average of molecular ensembles has been the conventional source of information on molecular structures, atomic resolution movies of single organic molecules obtained by single-molecule real-time transmission electron microscopy have recently emerged as a new tool to study the time evolution of the structures of individual molecules. The present work describes a proof-of-principle study of the determination of the conformation of each C-C bond in single perfluoroalkyl fullerene molecules encapsulated in a single-walled carbon nanotube (CNT) as well as those attached to the outer surface of a carbon nanohorn (CNH). Analysis of 82 individual molecules in CNTs under a 120 kV electron beam indicated that 6% of the CF2-CF2 bonds and about 20% of the CH2-CH2 bonds in the corresponding hydrocarbon analogue are in the gauche conformation. This comparison qualitatively matches the known conformational data based on time- and molecular-average as determined for ensembles. The transmission electron microscopy images also showed that the molecules entered the CNTs predominantly in one orientation. The molecules attached on a CNH surface moved more freely and exhibited more diverse conformation than those in a CNT, suggesting the potential applicability, of this method for the determination of the dynamic shape of flexible molecules and of detailed conformations. We observed little sign of any decomposition of the specimen molecules, at least up to 10(7) e.nm(-2) (electrons/nm(2)) at 120 kV acceleration voltage. Decomposition of CNHs under irradiation with a 300 kV electron beam was suppressed by cooling to 77 K, suggesting that the decomposition is a chemical process. Several lines of evidence suggest that the graphitic substrate and the attached molecules are very cold.