1,2-<2-(4-methoxybenzoyl)-4,5-dihydrooxazolo>-<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: 1,2-<2-(4-methoxybenzoyl)-4,5-dihydrooxazolo>-<60>fullerene
• 英文别名: 2-(4-methoxyphenyl)-oxazolo[4,5:1,2][60]fullerene
• 化学式: C₆₈H₇NO₂
• 分子量: 869.809
• InChiKey: VZDMIZHTRNINRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  71
• 可旋转键数：
  2
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,2--<60>fullerene 以 various solvent(s) 为溶剂， 反应 18.0h， 以92%的产率得到1,2-<2-(4-methoxybenzoyl)-4,5-dihydrooxazolo>-<60>fullerene
  参考文献：
  名称：

  将光化学生成的丙烯腈加到C 60中。Fulleroaziridines的合成和热重排为Fullerooxazoles

  摘要：

  由芳酰叠氮化物1在二氯甲烷中的光解产生的C 60与酰基硝烯2的反应产生了稳定的全氟叠氮吡啶衍生物3a，3b，3c和3d。通过在四氯乙烷中沸腾而使全氟氮丙啶3重排导致形成相应的全氟恶唑4a，4b，4c和4d。还通过在苯中辐照C 60和1b观察到了全氟恶唑4b的形成。

  DOI：

  10.1016/0040-4020(95)00013-x

文献信息

• Ferric perchlorate-mediated one-step reaction of [60]fullerene with primary amides for the synthesis of fullerooxazoles
  作者：Xiao-Feng Zhang、Fa-Bao Li、Ji-Long Shi、Jun Wu、Li Liu

  DOI：10.1039/c5nj02503f

  日期：——

  The reaction of [60]fullerene with amides promoted by cheap and easily available ferric perchlorate affords a series of interesting fullerooxazole derivatives.

  [60]富勒烯与酰胺在廉价且易获得的高氯酸铁的促进下，形成了一系列有趣的富勒氧唑衍生物。
• PhI(OAc)2/I2-mediated [3+2] reaction of [60]fullerene with amides for the preparation of fullerooxazoles
  作者：Hai-Tao Yang、Wen-Long Ren、Chun-Ping Dong、Yang Yang、Xiao-Qiang Sun、Chun-Bao Miao

  DOI：10.1016/j.tetlet.2013.09.002

  日期：2013.12

  An efficient synthesis of fullerooxazoles was developed via PhI(OAc)2/I2-mediated [3+2] reaction of C60 with amides under photo-irradiation. The reaction was tolerant to various aryl and alkyl amides. The reaction mechanism was investigated in detail and a radical pathway was proposed for the formation of fullerooxazoles. Further transformation of compound 2l allowed the easy conjunction of fullerooxazole

  在光照射下，通过PhI（OAc）2 / I 2介导的C 60与酰胺的[3 + 2]反应，开发了全氟恶唑的有效合成方法。该反应耐受各种芳基和烷基酰胺。详细研究了反应机理，并提出了形成全氟恶唑的自由基途径。化合物21的进一步转化使得富勒唑基部分易于与其他分子骨架结合。
• CuI-Catalyzed Oxidative [3 + 2] Reaction of Fullerene with Amidines or Amides Using Air as the Oxidant: Preparation of Fulleroimidazole or Fullerooxazole Derivatives
  作者：Hai-Tao Yang、Xi-Chen Liang、Yan-Hong Wang、Yang Yang、Xiao-Qiang Sun、Chun-Bao Miao

  DOI：10.1021/ol401909z

  日期：2013.9.20

  CuI-catalyzed oxidative reaction of amidines with C60 using air as the oxidant has been exploited for the easy preparation of fulleroimidazole derivatives. Furthermore, this kind of CuI-catalyzed [3 + 2] reaction has also been successfully applied in the synthesis of fullerooxazole derivatives starting from amides for the first time. The substrate scope is broad, and the process is particularly cheap

  利用CuI以空气为氧化剂，催化C与C 60的氧化反应已被广泛用于制备全咪唑衍生物。此外，这种由CuI催化的[3 + 2]反应也已成功地首次用于从酰胺开始的全氟恶唑衍生物的合成中。基材范围广，并且该方法特别便宜且简单。
• Synthesis of Fullerooxazoles: Novel Reactions of [60]Fullerene with Nitriles Promoted by Ferric Perchlorate
  作者：Fa-Bao Li、Tong-Xin Liu、Guan-Wu Wang

  DOI：10.1021/jo8007868

  日期：2008.8.1

  The ferric perchlorate-mediated reactions of C60 with various nitriles in o-dichlorobenzene under nitrogen atmosphere afforded the rare fullerooxazoles, which would be difficult to prepare by other methods. A possible reaction mechanism for the formation of the fullerooxazoles was proposed.

  在氮气氛下，高氯酸铁介导的C 60与各种腈在邻二氯苯中的反应提供了稀有的全氟恶唑，这很难用其他方法制备。提出了形成全氟恶唑的可能的反应机理。
• Copper-mediated synthesis of fullerooxazoles from [60]fullerene and <i>N</i>-hydroxybenzimidoyl cyanides
  作者：Qing-Song Liu、Wen-Jie Qiu、Wen-Qiang Lu、Guan-Wu Wang

  DOI：10.1039/d2ob00239f

  日期：——

  efficient copper-mediated [3 + 2] heteroannulation reaction of [60]fullerene with N-hydroxybenzimidoyl cyanides has been developed for the synthesis of fullerooxazoles. A possible reaction mechanism involving unique C–CN and N–OH bond cleavages and subsequent C–OH bond formation for N-hydroxybenzimidoyl cyanides is proposed to explain the generation of fullerooxazoles. In addition, the formed fullerooxazoles

  已经开发了一种新颖且有效的铜介导的[60]富勒烯与N-羟基苯并亚胺酰氰化物的[3 + 2]异环化反应，用于合成富勒恶唑。提出了一种可能的反应机制，涉及独特的 C-CN 和 N-OH 键断裂以及随后N-羟基苯并亚氨基氰化物的C-OH 键形成来解释富勒恶唑的产生。此外，形成的富勒恶唑可以进一步电化学转化为酰胺化的 1,2-氢化富勒烯。