叔丁基(1,2-亚甲基富勒烯C60)-61-羧酸酯 | 150493-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 叔丁基(1,2-亚甲基富勒烯C60)-61-羧酸酯
• 中文别名: (1,2-亚甲基富勒烯-C60)-61-羧酸叔丁酯
• 英文名称: tert-Butyl methgano[60]fullerene carboxylate
• 英文别名: 1,2-(3'-tert-butylformylcyclopropano)[60]fullerene；tert-butyl 3′H-cyclopropa[1,9](C₆₀-I_h)[5,6]fullerene-3′-carboxylate；tert-butyl 3'H-cyclopropa[1,9](C60-Ih)[5,6]fullerene-3'-carboxylate；tert-butyl (1,2-methanofullerene)-61-carboxylate；(1,2-Methanofullerene C60)-61-carboxylic acid tert-butyl ester
• CAS: 150493-29-1
• 化学式: C₆₆H₁₀O₂
• 分子量: 834.804
• InChiKey: YGTNZHVTMAQCFA-UHFFFAOYSA-N

物化性质

• 密度：
  2.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.1
• 重原子数：
  68
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  叔丁基(1,2-亚甲基富勒烯C60)-61-羧酸酯 在 1,10-菲罗啉 、 silver carbonate 作用下， 以 邻二氯苯 为溶剂， 反应 8.0h， 以45%的产率得到1,2-dihydromethano[60]fullerene
  参考文献：
  名称：

  Methanofullerenes, C₆₀(CH₂)_n (n = 1, 2, 3), as Building Blocks for High-Performance Acceptors Used in Organic Solar Cells

  摘要：

  Selective preparation of C-60(CH2)n (n = 1, 2, 3) was realized via a "Bingel-decarboxylation" route. A 54 pi-electron derivative of C-60(CH2)(2), OQBMF, demonstrates an outstanding power conversion efficiency (PCE) of 6.43% (V-oc = 0.95 V, J(sc),c = 9.67 mA cm(-2), FF = 70%) in fullerene:P3HT solar cells since the small CH2 addends lift up fullerene LUMO and increase V-oc, significantly without decreasing mobility significantly.

  DOI：

  10.1021/ol4035275
• 作为产物：
  描述：

  di-tert-butyl methano[60]fullerene-61,61-dicarboxylate 以 邻二氯苯 为溶剂， 反应 6.0h， 以100%的产率得到叔丁基(1,2-亚甲基富勒烯C60)-61-羧酸酯
  参考文献：
  名称：

  Methanofullerenes, C₆₀(CH₂)_n (n = 1, 2, 3), as Building Blocks for High-Performance Acceptors Used in Organic Solar Cells

  摘要：

  Selective preparation of C-60(CH2)n (n = 1, 2, 3) was realized via a "Bingel-decarboxylation" route. A 54 pi-electron derivative of C-60(CH2)(2), OQBMF, demonstrates an outstanding power conversion efficiency (PCE) of 6.43% (V-oc = 0.95 V, J(sc),c = 9.67 mA cm(-2), FF = 70%) in fullerene:P3HT solar cells since the small CH2 addends lift up fullerene LUMO and increase V-oc, significantly without decreasing mobility significantly.

  DOI：

  10.1021/ol4035275

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。
• Synthesis of fullerene C60 monoadducts. Cyclopropanation of C60 with sulfonium ylides
  作者：D. N. Nikolaev、P. B. Davidovich、L. B. Piotrovskii

  DOI：10.1134/s107042801607023x

  日期：2016.7

  3′H-Cyclopropa[1,9](C60-I h )[5,6]fullerene-3′-carboxylic acid can be synthesized in a good yield by cyclopropanation of fullerene C60 with 2-(dimethyl-λ4-sulfanylidene)acetates provided that the ester residue is readily hydrolyzable in acid medium.

  3' ħ -Cyclopropa [1,9]（C 60 -我 ħ）[5,6]富勒烯-3'-羧酸可以以良好的产率来合成由富勒烯C的环丙烷化60用2-（二甲基- λ 4 -亚磺酰基乙酸酯），条件是该酯残基在酸性介质中易于水解。
• Structures and Chemistry of Methanofullerenes: A Versatile Route intoN-[(Methanofullerene)carbonyl]-Substituted Amino Acids
  作者：Lyle Isaacs、Fran�ois Diederich

  DOI：10.1002/hlca.19930760705

  日期：1993.11.3

  higher single-bond character at 6-5 bonds. Reaction of C60 with diazo diester 15 gave the fullerene diester 14 which was hydrolyzed with BBr3 in benzene to the methanofullerenecarboxylic acid 10, a versatile synthon for the preparation of amphiphilic fullerene derivatives. Treatment of 10 with alcohols and amino acid esters under DCC coupling conditions afforded the esters 5 and 17 and the amino-acid

  C 60与恶二唑13的反应以32％的产率提供了二甲氧基甲基富勒烯7，为具有闭合的跨环键的6-6环桥联的异构体。文献调查显示，所有6-6环桥联的亚甲基富勒烯均为带有封闭的跨环键（6-6-封闭）的σ-芳香族芳香族化合物，所有6-5环桥联的都是具有开放式跨环键的π-芳香族芳香族（6 -5-打开）。对6-6封闭和6-5-开放结构的偏爱不是由于取代基效应引起的，而是用这些异构体中在C 60中看到的有利键的保守性进行了最好的解释，C 60在6-6键上具有较高的双键特性和更高的单键性状（6-5个键）。C 60与重氮二酯15的反应将得到的富勒烯二酯14与苯中的BBr 3水解为亚甲基富勒烯羧酸10，后者是一种用于制备两亲性富勒烯衍生物的通用合成子。在DCC偶联条件下用醇和氨基酸酯处理10，分别得到酯5和17以及氨基酸衍生物11和12。
• Synthesis of C60-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates
  作者：Guan-Wu Wang、Jia-Xing Li、Yu Xu

  DOI：10.1039/b807394e

  日期：——

  Nucleophilic cycloaddition of thiocyanates 1a–e with C60 in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene afforded C60-fused 2-iminotetrahydrothiophene derivatives 2a–e and methanofullerenes 3a–d. The product distributions were highly sensitive to the substrates employed. The 2-iminotetrahydrothiophene derivatives 2a–e could be further manipulated by hydrolysis and acetylation to give 2-oxotetrahydrothiophene derivatives 4a–e and 2-acetamidotetrahydrothiophene derivatives 5a–e. A possible reaction mechanism for the formation of products 2a–e and 3a–d was proposed.

  噻吩氰酸盐1a–e与C60在1,8-二氮-双环[5.4.0]十一烯存在下进行亲核环加成反应，生成C60融合的2-亚氨基四氢噻吩衍生物2a–e和甲烷全氟烯3a–d。产物分布对所采用的底物非常敏感。2-亚氨基四氢噻吩衍生物2a–e可通过水解和乙酰化进一步转化为2-氧四氢噻吩衍生物4a–e和2-乙酰基四氢噻吩衍生物5a–e。提出了生成产物2a–e和3a–d的可能反应机理。
• Palladium-catalyzed selective cycloaddition of diazo compounds to [60]fullerene
  作者：Airat Ramilevich Tuktarov、Arslan Rifkhatovich Akhmetov、Vyacheslav Vladimirovich Korolev、Artur Albertovich Khuzin、Liliya Linatovna Khasanova、Natalya Romanovna Popodko、Leonard Mukhibovich Khalilov、Usein Memetovich Dzhemilev

  DOI：10.3998/ark.5550190.0012.804

  日期：——

  The effective catalytic method for cycloaddition of higher diazoalkanes and diazoacetates to [60]fullerene in the presence of the three-component catalytic system Pd(acac)2–PPh3–Et3Al has been developed. The yield and selective formation of the target homo- and methanofullerenes are dependent upon the structure of the original diazo compounds.

  已经开发了在三组分催化体系 Pd(acac)2–PPh3–Et3Al 存在下，将高级重氮烷烃和重氮乙酸酯环加成为 [60] 富勒烯的有效催化方法。目标均富勒烯和甲烷富勒烯的产率和选择性形成取决于原始重氮化合物的结构。