1,2,4,11,15,30-hexakis(tert-butylperoxy)-1,2,4,11,15,30-hexahydro[60]fullerene | 686766-94-9

• 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: 1,2,4,11,15,30-hexakis(tert-butylperoxy)-1,2,4,11,15,30-hexahydro[60]fullerene
• 英文别名: 1,2,4,11,15,30-hexa-tert-butylperoxy-1,2,4,11,15,30-hexahydro[60]fullerene
• CAS: 686766-94-9
• 化学式: C₈₄H₅₄O₁₂
• 分子量: 1255.35
• InChiKey: NRPPERBGBQTRTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.3
• 重原子数：
  96.0
• 可旋转键数：
  12.0
• 环数：
  32.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  110.76
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,2,4,11,15,30-hexakis(tert-butylperoxy)-1,2,4,11,15,30-hexahydro[60]fullerene 在 足球烯 作用下， 以 氯苯 为溶剂， 反应 1.08h， 以20%的产率得到
  参考文献：
  名称：

  Synthesis of Fullerene Oxides Containing Both 6,6-Closed Epoxide and 5,6-Open Ether Moieties through Thermolysis of Fullerene Peroxides

  摘要：

  Thermolysis of the fullerene hexaadduct C-60(OO'Bu)(6) results in cleavage of two O-O bonds and elimination of two tert-butoxy groups to form two isomeric products with the formula C-60(O)(2)(OO'Bu)(4) in comparable yields. The two oxygen atoms exist as two epoxy groups in one isomer 3, and as an epoxy and an ether group in the other isomer 2. Addition of hydroxylamine to 2 opens both the epoxy and the ether moieties to give a cage-opened keto-ketoxime derivative.

  DOI：

  10.1021/jo9000977
• 作为产物：
  描述：

  叔丁基过氧化氢 、 1,2,4,15-tetrakis(t-butylperoxy)-1,2,4,15-tetrahydro[60]fullerene 在 碘苯二乙酸 作用下， 反应 0.08h， 生成 1,2,4,11,15,30-hexakis(tert-butylperoxy)-1,2,4,11,15,30-hexahydro[60]fullerene
  参考文献：
  名称：

  Selective Preparation of Oxygen-Rich [60]Fullerene Derivatives by Stepwise Addition of tert-Butylperoxy Radical and Further Functionalization of the Fullerene Mixed Peroxides

  摘要：

  tert-Butylperoxy radicals add to C-60 selectively to form multi-adducts C-60(O)(m)((OOBu)-Bu-t), (m = 0, n = 2, 4, 6; m = 1, n = 0, 2, 4, 6) in moderate yields under various conditions. Visible light irradiation favors epoxide formation. High concentration of tert-butylperoxy radicals mainly produces the hexa-homoadduct C-60((OOBu)-Bu-t)(6) 6; low concentration and long reaction time favor the epoxy-containing C-60(O)((OOBu)-Bu-t)(4) 7. The reaction can be stopped at the bis-adducts with limited TBHP. A stepwise addition mechanism is discussed involving mono-, allyl-, and cyclopentadienyl C-60 radical intermediates. m-CPBA reacts with the 1,4-bis-adduct to form C-60(O)((OOBu)-Bu-t)(2) and C-60(O)(3)((OOBu)-Bu-t)(2). The C-O bond of the epoxy ring in 7 can be cleaved with HNO3 and CF3COOH. Nucleophilic addition of NaOMe to 7 follows the S(N)1 and extended S(N)2' mechanism, from which four products are isolated with the general formula C-60(O)(a)(OH)(b)(OMe)(c)((OOBu)-Bu-t)(d). Visible light irradiation of the hexa-adduct 6 results in partial cleavage of both the C-O and O-O bonds of peroxide moieties and formation of the cage-opened compound C-60(O)(O)(2)((OOBu)-Bu-t)(4). All the fullerene derivatives are characterized by spectroscopic data. A single-crystal structure has been obtained for an isomer Of C-60(O)(OH)(2)(OMe)(4)((OOBu)-Bu-t)(2).

  DOI：

  10.1021/jo049974q

文献信息

• Punching a Carbon Atom of C ₆₀ into its Own Cavity to Form an Endohedral Complex CO@C ₅₉ O ₆ under Mild Conditions
  作者：Lijun Shi、Dazhi Yang、Francesca Colombo、Yuming Yu、Wen‐Xiong Zhang、Liangbing Gan

  DOI：10.1002/chem.201303501

  日期：2013.12.2

  Punching the ball: By using multistep chemical reactions as a “can opener”, a half circle opening is cut around a pentagon in C60 to form an open‐cage fullerene with an 18‐membered orifice. During the process, one carbon atom in the fullerene skeleton is eliminated into the cavity as carbon monoxide to form a stable endohedral complex CO@C59O6 (see figure). The single‐crystal X‐ray structure shows

  冲球：通过使用多步化学反应作为“开罐器”，在C 60中的五边形处切一个半圆的开口，形成带有18元孔的开笼式富勒烯。在此过程中，富勒烯骨架中的一个碳原子作为一氧化碳被排入空腔，形成了稳定的内六面体复合物CO @ C 59 O 6（见图）。X射线单晶结构表明，被捕的一氧化碳与笼子之间具有很强的偶极-偶极相互作用。
• Lewis Acid Promoted Preparation of Isomerically Pure Fullerenols from Fullerene Peroxides C₆₀(OO<i>t</i>-Bu)₆ and C₆₀(O)(OO<i>t</i>-Bu)₆
  作者：Fudong Wang、Zuo Xiao、Zhipeng Yao、Zhenshan Jia、Shaohua Huang、Liangbing Gan、Jiang Zhou、Gu Yuan、Shiwei Zhang

  DOI：10.1021/jo060012o

  日期：2006.6.1

  Fullerene mixed peroxides C-60(t-BuOO)(6) and C-60(O)(t-BuOO)(6) react with Lewis acids to form various fullerenols through the partial fragmentation of t-BuOO groups. Two monohydroxyl fullerenols with the general formula C-60(OH)(t-BuOO)(5) and six monohydroxyl fullerenols with the general formula C-60(O)(OH)(t-BuOO)(5) were prepared, which are essentially the same except the location of the OH group. An additional reaction of the monohydroxyl fullerenols gave bis- and trishydroxyl fullerenols. Single-crystal X-ray structures have been obtained for the two monohydroxyl fullerenols. Other compounds are characterized by chemical correlation and their spectroscopic data. Cuprous bromide could protect the most reactive t-BuOO group from being attacked by stronger Lewis acids. The proposed mechanism mainly involves Lewis acid induced heterolysis of the peroxo O-O bond.