1,2-(2-benzoyl-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-benzoyl-4,5-dihydrooxazolo)-<60>fullerene
• 英文别名: 2-phenyl-oxazolo[4,5:1,2][60]fullerene
• 化学式: C₆₇H₅NO
• 分子量: 839.783
• InChiKey: ODPMTWZXPQRUKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  69
• 可旋转键数：
  1
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-(2-benzoyl-4,5-dihydrooxazolo)-<60>fullerene 在 四丁基高氯酸铵 作用下， 以 苯甲腈 为溶剂， 生成
  参考文献：
  名称：

  Electrochemical and H/D-Labeling Study of Oxazolino[60]Fullerene Rearrangement

  摘要：

  Isomerization of an oxazoline cycle from a [6,6]- to [5,6]-junction on the C(60) sphere of dianionic [60]fullero-oxazoline (1(2-)) during a 1,4-addition is studied by electrochemistry and a stepwise addition of PhCH(2)Br and PhCD(2)Br. Cyclic voltammerty of the in situ generated 1(2-) shows a very unusual positive shift for the anodic peak corresponding to the oxidation of 1(2-), indicating that the C(60) cage of dianionic 1 bears only one unit negative charge due to the heterolytic cleavage of the C(60)-O bond. Further study with a stepwise addition of PhCH(2)Br and PhCD(2)Br, which are used to differentiate the aryl groups added at each step onto dianionic 1, shows explicitly there is an exclusive selectivity of the C-O bond for the ring-opening and ring-closure during the isomerization of the heterocycle. A reaction mechanism is proposed on the basis of the experimental results and computational calculations.

  DOI：

  10.1021/jo1023798
• 作为产物：
  描述：

  1,2-(N-benzoylaziridino)-<60>fullerene 以 various solvent(s) 为溶剂， 反应 18.0h， 以90%的产率得到1,2-(2-benzoyl-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。
• Cu(OAc)₂-Mediated Reaction of C₆₀ with Ureas for the Preparation of Fulleroimidazolidinones
  作者：Hai-Tao Yang、Yi-Chen Tan、Yang Yang、Xiao-Qiang Sun、Chun-Bao Miao

  DOI：10.1021/acs.joc.5b02682

  日期：2016.2.5

  The Cu(OAc)2-mediated intermolecular diamination reaction of C60 with ureas allows the concise and efficient preparation of fulleroimidazolidinones involving the cleavage of two N–H bonds and formation of two C–N bonds. Both dialkylated and diarylated fulleroimidazolidinones can be synthesized using this method.

  Cu（OAc）2介导的C 60与脲的分子间胺化反应使得简明而高效的全咪唑啉酮类化合物的制备涉及两个N–H键的断裂和两个C–N键的形成。可以使用该方法合成二烷基化和二芳基化的全氨基咪唑啉酮。
• Hydroxide-Initiated Conversion of Aromatic Nitriles to Imidazolines: Fullerenes vs TCNE
  作者：Hui-Lei Hou、Zong-Jun Li、Shu-Hui Li、Si Chen、Xiang Gao

  DOI：10.1021/ol401834j

  日期：2013.9.20

  aromatic nitriles to imidazolines has been achieved under basic conditions with the electron-deficient C60 and C70 fullerenes, but not with the electron-deficient olefin of tetracyanoethylene (TCNE). In situ UV–vis–NIR indicates that the ability of RC60– to undergo single-electron transfer (SET) to C60 is crucial for the reaction.

  在碱性条件下，使用缺电子的C 60和C 70富勒烯，但未使用缺电子的四氰基乙烯的烯烃（TCNE），可以实现芳族腈向咪唑啉的转化。原位的UV-vis-NIR表明RC的能力60 -接受单电子转移（SET）至C 60是用于该反应的关键。
• 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。