| 175875-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 175875-69-1
• 化学式: C₆₆H₁₁NO₂
• 分子量: 849.819
• InChiKey: HQVPPFHGAZGLLS-UHFFFAOYSA-N

物化性质

• 密度：
  2.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.9
• 重原子数：
  69
• 可旋转键数：
  3
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  反应 0.17h， 以99%的产率得到足球烯
  参考文献：
  名称：

  Metal-free, retro-cycloaddition of fulleropyrrolidines in ionic liquids under microwave irradiation

  摘要：

  在微波辐照下，离子液体可在几分钟内将富勒吡咯烷定量环化为 [60] 富勒烯，而无需任何其他添加剂。

  DOI：

  10.1039/b906813a
• 作为产物：
  描述：

  肌氨酸乙酯盐酸盐 、 足球烯 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 生成 、
  参考文献：
  名称：

  Synthesis of Fullerene Amino Acid Derivatives by Direct Interaction of Amino Acid Ester with C₆₀

  摘要：

  Amino acid esters react with C-60 both thermally and photochemically to give different products. Refluxing a mixture of C-60 and glycine ethyl ester afforded C-60(Me(2)CHNHCHCOOEt) 1, whereas irradiation of the same mixture produced C-60(EtOOCCHNHCHCOOEt) 2b as the main product. Photochemical reactions between C-60 and sarcosine esters yielded two pyrrolidine derivatives C-60(CH2N(Me)CHCOOR)3 and C-60(ROOCCHNHCHCOOR) 2 (R = Me, Et, CH(2)Ph). Compound 2a is also prepared from the photochemical reaction between C-60 and iminodiacetic methyl ester in high yield. These ester derivatives are difficult to hydrolyze in excess mineral acids. The fullerene dicarboxylic acid C-60(HOOCCHNHCHCOOH) 5 is synthesized from the tert-butyl derivative C-60((t)BuOOCCHNHCHCOO(t)Bu) 4. A possible radical reaction mechanism for the photochemical reactions is proposed which involves an unprecedented C-N bond breakage.

  DOI：

  10.1021/jo951933u

文献信息

• Reactions of [60]Fullerene with Halides and Amino Acids to Synthesize Fulleropyrrolidines
  作者：Bo Jin、Juan Shen、Rufang Peng、Congdi Chen、Shijin Chu

  DOI：10.1002/ejoc.201402655

  日期：2014.10

  discovery of other halides – such as allyl chloride, methallyl chloride, cinnamyl chloride, propargyl bromide, ethyl bromoacetate, bromoacetonitrile, bromomethane, bromopropane and bromobutane – that could also react with [60]fullerene and amino acids to produce fulleropyrrolidines. This reaction could be an alternative to the Prato reaction for synthesizing fulleropyrrolidines when aldehydes are expensive

  研究了 [60] 富勒烯与苄基氯和氨基酸在氯苯 (PhCl) 中的反应。从这些反应中获得了带有来自相应苄基氯的 ArCH 部分的富勒吡咯烷，通过 C-Cl 键断裂。使用PhCl/DMSO代替PhCl作为溶剂显着提高了反应效率。对这些反应的详细研究导致发现了其他卤化物——如烯丙基氯、甲基烯丙基氯、肉桂酰氯、炔丙基溴、溴乙酸乙酯、溴乙腈、溴甲烷、溴丙烷和溴丁烷——它们也可以与 [60] 富勒烯和氨基反应酸生成富勒吡咯烷。当醛价格昂贵或无法从商业来源获得时，该反应可以替代普拉托反应来合成富勒吡咯烷。提出了一种可能的产物形成反应机制，包括卤化物中的 C-X 键断裂形成醛。
• On the Mechanism of the Thermal Retrocycloaddition of Pyrrolidinofullerenes (Retro-Prato Reaction)
  作者：Salvatore Filippone、Marta Izquierdo Barroso、Ángel Martín-Domenech、Sílvia Osuna、Miquel Solà、Nazario Martín

  DOI：10.1002/chem.200800096

  日期：2008.6.9

  In contrast to N-methyl or N-unsubstituted pyrrolidinofullerenes, which efficiently undergo the retrocycloaddition reaction to quantitatively afford pristine fullerene, N-benzoyl derivatives do not give this reaction under the same experimental conditions. To unravel the mechanism of the retrocycloaddition process, trapping experiments of the in-situ thermally generated azomethine ylides, with an efficient

  与有效地进行逆向加成反应以定量得到原始富勒烯的N-甲基或N-未取代的吡咯烷基富勒烯相反，N-苯甲酰基衍生物在相同的实验条件下不进行该反应。为了弄清逆环加成过程的机理，进行了原位热生成的偶氮甲亚胺基团与有效的双亲亲油团的捕集实验。这些实验提供了作为内/外异构体混合物的各个环加合物。在DFT级别并通过使用两层ONIOM（我们自己的n层集成分子轨道和分子力学）方法进行的理论计算为实验结果奠定了基础，并预测存在二烯体不是对甲硫氨酸的基本要求叶立德能够在热条件下离开富勒烯表面。一旦在反应介质中生成了1,3-偶极子，它就会被亲偶极子（马来酸酐或N-苯基马来酰亚胺）有效地捕获。然而，对于N-未取代的吡咯烷基富勒烯，亲核试剂在整个反应路径中参与协助1，3-偶极子离开富勒烯表面也是一种可能的机制，不能排除。3-偶极子在反应介质中生成，被偶极亲子（马来酸酐或N-苯基马来酰亚胺）有效地捕获。然而，对于N-未取代
• Study on the thermal reactions of [60]fullerene with amino acids and amino acid esters
  作者：San-E Zhu、Xin Cheng、Yu-Jin Li、Cheng-Kang Mai、Yong-Shun Huang、Guan-Wu Wang、Ru-Fang Peng、Bo Jin、Shi-Jin Chu

  DOI：10.1039/c2ob26066b

  日期：——

  Thermal reactions of [60]fullerene with a series of amino acids and amino acid esters under aerobic and dark conditions have been investigated. Fulleropyrrolidines can be obtained from these reactions although an aldehyde is not added purposely. Possible reaction mechanisms involving uncommon C–N bond cleavages have been proposed to generate aldehydes, which then react with amino acids and amino acid

  研究了[60]富勒烯与一系列氨基酸和氨基酸酯在好氧和黑暗条件下的热反应。尽管没有有意地添加醛，但是从这些反应可以获得全吡咯烷。已经提出了可能的涉及罕见的C–N键断裂的反应机理，以生成醛，然后与氨基酸和氨基酸酯反应生成甲亚胺基团，然后将1,3-偶极环加成生成[60]富勒烯，从而得到全吡咯烷。对照实验支持我们提出的机制，并阐明了氨基酸和氨基酸酯的C–N键裂解的先天性。
• Retro-Cycloaddition Reaction of Pyrrolidinofullerenes
  作者：Nazario Martín、Margarita Altable、Salvatore Filippone、Angel Martín-Domenech、Luis Echegoyen、Claudia M. Cardona

  DOI：10.1002/anie.200502556

  日期：2006.1
• Synthesis of Fullerene Amino Acid Derivatives by Direct Interaction of Amino Acid Ester with C₆₀
  作者：Liangbing Gan、Dejian Zhou、Chuping Luo、Haisong Tan、Chunhui Huang、Mujian Lü、Jinqi Pan、Yi Wu

  DOI：10.1021/jo951933u

  日期：1996.1.1

  Amino acid esters react with C-60 both thermally and photochemically to give different products. Refluxing a mixture of C-60 and glycine ethyl ester afforded C-60(Me(2)CHNHCHCOOEt) 1, whereas irradiation of the same mixture produced C-60(EtOOCCHNHCHCOOEt) 2b as the main product. Photochemical reactions between C-60 and sarcosine esters yielded two pyrrolidine derivatives C-60(CH2N(Me)CHCOOR)3 and C-60(ROOCCHNHCHCOOR) 2 (R = Me, Et, CH(2)Ph). Compound 2a is also prepared from the photochemical reaction between C-60 and iminodiacetic methyl ester in high yield. These ester derivatives are difficult to hydrolyze in excess mineral acids. The fullerene dicarboxylic acid C-60(HOOCCHNHCHCOOH) 5 is synthesized from the tert-butyl derivative C-60((t)BuOOCCHNHCHCOO(t)Bu) 4. A possible radical reaction mechanism for the photochemical reactions is proposed which involves an unprecedented C-N bond breakage.