spiro[C60-anthrone] | 173929-44-7

• 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: spiro[C60-anthrone]
• CAS: 173929-44-7
• 化学式: C₇₄H₈O
• 分子量: 912.877
• InChiKey: TWYVFSWGGGFMNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.3
• 重原子数：
  75
• 可旋转键数：
  0
• 环数：
  36.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  spiro[C60-anthrone] 以 四氢呋喃 为溶剂， 以41%的产率得到足球烯
  参考文献：
  名称：

  Reductive Electrochemistry of Spiromethanofullerenes

  摘要：

  The synthesis and electrochemical properties of spiromethanofullerenes 1-6 are described. The syntheses were achieved via the diazomethane route, and the regioisomeric distribution of bis-adducts 3 was determined by H-1 NMR, UV-vis, and HPLC analysis. The electrochemistry of these compounds in dichloromethane exhibits, besides several reversible reductions, some irreversible waves. Reductive electrolysis of 1 and 3-5 in dichloromethane leads to the removal of the addend and thus to the formation of C-60 Reductive electrolysis of 1, 2 and 6 in dichloromethane leads to a different reaction, which we tentatively assign to a reaction with the solvent to form fullerene-CH2Cl products. Electrolyses in the less reactive solvent THF lead to adduct removal for 1 and 3-5. Interestingly, significant formation of bis-adducts from the corresponding monoadducts was observed for 4 and 5. These electrochemically induced reactions, namely addend removal, reaction with the solvent, and addend transfer are influenced by the structure of the addend and by the choice of solvent.

  DOI：

  10.1021/jo010297z
• 作为产物：
  描述：

  10-重氮基-9(10H)-蒽酮 、 足球烯 以 邻二氯苯 为溶剂， 反应 0.67h， 以39%的产率得到spiro[C60-anthrone]
  参考文献：
  名称：

  Cycloadditions to [60]fullerene using microwave irradiation: A convenient and expeditious procedure

  摘要：

  Several Diels-Alder and 1,3-dipolar cycloadditions to C-60 were performed, under microwave irradiation, in a modified domestic microwave oven and a focused microwave reactor. Reactions proceed within minutes to afford the respective cycloadducts in similar or increased yields related to the described methods by conventional heating. This methodology simplifies the procedure and overcomes the drawbacks resulting from the long reaction times required under classical heating conditions. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01150-7

文献信息

• Synthesis and Electrochemistry of Electronegative Spiroannelated Methanofullerenes:  Theoretical Underpinning of the Electronic Effect of Addends and a Reductive Cyclopropane Ring-Opening Reaction
  作者：Brian Knight、Nazario Martín、Toshinobu Ohno、Enrique Ortí、Concepció Rovira、Jaume Veciana、José Vidal-Gancedo、Pedro Viruela、Rafael Viruela、Fred Wudl

  DOI：10.1021/ja962299k

  日期：1997.10.1

  and the TCNQ- and DCNQI-type derivatives (10 and 11) were isolated as [6,6] adducts. The spiro[cyclohexanone-4,61‘-methanofullerene] (6) was however obtained as a mixture of [5,6] and [6,6] isomers. The novel methanofullerenes, with the only exception of 6, show irreversible cyclic voltammograms with additional reduction peaks. The conjugated cyclohexadienone derivatives 3 exhibit better acceptor abilities

  已经制备了带有醌型加成物的螺环烷化甲烷富勒烯，包括 TCNQ 和 DCNQI 类似物（3a-c、6a、b、8、10 和 11），并通过实验技术和量子化学计算表征了它们的结构和电子特性. 螺[2,5-环己二烯酮-4,61'-甲基富勒烯]衍生物（3a-c）、螺[10-蒽酮-9,61'-甲基富勒烯]（8）以及TCNQ-和DCNQI-型衍生物(10 和 11) 被分离为 [6,6] 加合物。然而，螺[环己酮-4,61'-甲氧基富勒烯](6)作为[5,6]和[6,6]异构体的混合物获得。新的甲烷富勒烯，除了 6 种外，显示出不可逆的循环伏安图和额外的还原峰。共轭环己二烯酮衍生物 3 表现出比母体 C60 更好的受体能力。