61-Hydroxy-1,9-(methano<1,2>benzenomethano)fullerene<60> | 157731-67-4

• 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: 61-Hydroxy-1,9-(methano<1,2>benzenomethano)fullerene<60>
• 英文别名: Tritriacontacyclo[62.4.0.03,58.03,62.04,20.05,57.06,18.07,55.08,17.09,53.010,15.011,52.012,49.013,47.014,44.016,43.019,42.021,41.022,62.023,39.024,61.025,37.026,35.027,60.028,33.029,59.030,56.031,54.032,51.034,50.036,48.038,46.040,45]octahexaconta-1(68),4,6(18),7,9(53),10(15),11,13,16,19,21,23,25,27,29(59),30(56),31,33,35,37,39,41,43,45,47,49,51,54,57,60,64,66-dotriacontaen-2-ol
• CAS: 157731-67-4
• 化学式: C₆₈H₈O
• 分子量: 840.811
• InChiKey: BKZAIXQQOPRWBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  69
• 可旋转键数：
  0
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  61-Hydroxy-1,9-(methano<1,2>benzenomethano)fullerene<60> 在 pyridinium chlorochromate 作用下， 以 二硫化碳 、 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到
  参考文献：
  名称：

  带有羟基的[60]富勒烯-邻-喹二甲烷加合物的光化学合成，构象分析和转化。

  摘要：

  研究了[60]富勒烯与在邻位带有烷基的各种芳族醛或酮1a-n的光化学反应。他们中的一些提供了带有连接在环己烯环上的羟基的稳定的邻喹二甲烷加合物2。发现加合物2采用两个构象剂A和E之一或两者，它们分别具有伪轴和伪赤道羟基。构象比明显取决于与芳族核和环己烯环相连的取代基。还通过VT-NMR技术研究了2的动力学行为。

  DOI：

  10.1021/jo0161328
• 作为产物：
  描述：

  1-羟基-苯并环丁烯 、 足球烯 以 甲苯 为溶剂， 生成 61-Hydroxy-1,9-(methano<1,2>benzenomethano)fullerene<60>
  参考文献：
  名称：

  光化学生成羟基的C60的Diels-Alder环加成反应由立体因素控制的邻喹啉甲烷：机理研究

  摘要：

  光酚反应性中间体会添加到C 60中，生成稳定的[4 + 2]富勒烯加合物。主要基于分子内和分子间动力学同位素效应（KIEs）研究，提供了一种用于C 60反应性的机械方法。

  DOI：

  10.1002/ejoc.201900859

文献信息

• Covalent attachment of various substituents in closest proximity to the C60-core: A broad synthetic approach to stable fullerene derivatives
  作者：Alexander Kraus、Andreas Gügel、Pavel Belik、Michael Walter、Klaus Müllen

  DOI：10.1016/0040-4020(95)00567-r

  日期：1995.1

  alpha-Substituted o-quinodimethanes facilitate the covalent attachment of many attractive molecules in closest proximity to the C-60-core. Thermal isomerization of various (+/-)-hydroxybenzocyclobutene esters 4, 8, 10 and 13 in the presence of C-60 provided the corresponding fullerene adducts 5(n), 7(n), 9(n), 11(n) and 12(n) in high yields. Using a dumbbell shaped bis-o-quinodimethane precursor 19, accessible from (+/-)-7-hydroxybenzocyclobutene and dodecanedicarboxylic acid dichloride, a soluble C-60-containing polymer 20 was formed.
• Reaction of C60 with Benzocyclobutenol: Expeditious Route to Fullerene Adducts
  作者：Xiaojun Zhang、Christopher S. Foote

  DOI：10.1021/jo00097a026

  日期：1994.9

  Reaction of C-60 with benzocyclobutenol (2a) and its methoxy ether (2b) in refluxing toluene gave 1,9-dihydrofullerene cycloadducts a and 3b in 59% and 50% yields, respectively. The alcohol was converted to pyranyl ether (4), acrylate (5), p-vinylbenzoate (6) and acid succinate esters (7) in good yields under very mild conditions. The adducts exist as two interconverting boat conformers. Acrylate 5 and p-vinylbenzoate 6 should be useful for polymerization studies. Acid 7 shows enhanced solubility in polar solvents.
• Facile modification of [60]fullerene by photochemically generated hydroxy-o-quinodimethane derivatives
  作者：Kyoji O-kawa、Yosuke Nakamura、Jun Nishimura

  DOI：10.1016/s0040-4039(00)00318-x

  日期：2000.4

  o-Quinodimethane derivatives generated by a simple photolysis of commercially available o-tolualdehyde and related compounds efficiently reacted with [60]fullerene to give stable adducts possessing a hydroxy group which is applicable to further functionalization. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Photochemical Synthesis, Conformational Analysis, and Transformation of [60]Fullerene−<i>o</i>-quinodimethane Adducts Bearing a Hydroxy Group
  作者：Yosuke Nakamura、Kyoji O-kawa、Satoshi Minami、Toshio Ogawa、Seiji Tobita、Jun Nishimura

  DOI：10.1021/jo0161328

  日期：2002.2.1

  photochemical reactions of [60]fullerene with various aromatic aldehydes or ketones 1a-n carrying an alkyl group at the ortho position were examined. Some of them afforded stable o-quinodimethane adducts 2 with a hydroxy group attached to the cyclohexene ring. The adducts 2 were found to adopt one or both of two conformers A and E, which possess pseudoaxial and pseudoequatorial hydroxy groups, respectively. The

  研究了[60]富勒烯与在邻位带有烷基的各种芳族醛或酮1a-n的光化学反应。他们中的一些提供了带有连接在环己烯环上的羟基的稳定的邻喹二甲烷加合物2。发现加合物2采用两个构象剂A和E之一或两者，它们分别具有伪轴和伪赤道羟基。构象比明显取决于与芳族核和环己烯环相连的取代基。还通过VT-NMR技术研究了2的动力学行为。
• Diels-Alder Cycloaddition of C₆₀ with Photochemically Generated Hydroxy to <i>o</i> -quinodimethanes Governed by Steric Factors: A Mechanistic Study
  作者：Manolis M. Roubelakis、Nikitas G. Malliaros、Michael Orfanopoulos

  DOI：10.1002/ejoc.201900859

  日期：2019.9.8

  intermediates add to C60, producing stable [4+2] fullerene adducts. A mechanistic approach for this reactivity of C60 is provided, based mainly on intra‐ and intermolecular kinetic isotope effects (KIEs) studies.

  光酚反应性中间体会添加到C 60中，生成稳定的[4 + 2]富勒烯加合物。主要基于分子内和分子间动力学同位素效应（KIEs）研究，提供了一种用于C 60反应性的机械方法。