1,4-二氢-1,4-甲桥蒽-9,10-二酮 | 32745-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1,4-二氢-1,4-甲桥蒽-9,10-二酮
• 英文名称: methanoanthraquinone
• 英文别名: 1,4-dihydro-1,4-methano-anthracene-9,10-dione；9.10-Dioxo-1.4-methylen-1.4.9.10-tetrahydro-anthracen；1,4-Dihydro-1,4-methano-anthracen-9,10-dion；1.4-Methylen-1.4-dihydro-anthrachinon；1,4-Dihydro-1,4-methanoanthracene-9,10-dione；tetracyclo[10.2.1.02,11.04,9]pentadeca-2(11),4,6,8,13-pentaene-3,10-dione
• CAS: 32745-55-4
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: UGTIHRDRMFXRLO-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C
• 沸点：
  409.0±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  1,4-二氢-1,4-甲桥蒽-9,10-二酮 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以64%的产率得到2α,3α-epoxy-1α,4α-dihydro-1,4-methanoanthracene-9,10-dione
  参考文献：
  名称：

  Synthesis and acid- and base-promoted ring opening of polycarbocyclic oxiranes

  摘要：

  Acid promoted ring opening of 1 alpha,4 alpha,4a alpha,9a alpha-tetrahydro-2 beta-3 beta-epoxy-1,4-methanoanthracene-9,10-dione and the corresponding 2-methyl derivative (i.e., 3a and 3b, respectively) afforded 4a and 46 in 26% and 49% yield, respectively. Similar results were obtained when a solution of either 3a or 3b in aqueous acetone was reacted with Na2CO3 at ambient temperature for 2 days. However, reaction of 3b with aqueous methanolic NaOH (ambient temperature, 7 days) produced a small quantity of 46 along with a novel pentacyclic diketone, 6b (44% yield). Finally, acid promoted ring opening of 1 alpha,4 alpha-dihydro-4a alpha,9a alpha-epoxy-1,4-methanoanthracene-9,10-dione (12) resulted in extensive skeletal rearrangement of the substrate, thereby affording 14 in low yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00162-8
• 作为产物：
  描述：

  exo tetracyclo<10.2.1.0^2,11.0^4,9>pentadeca-4,5,7,13-tetraene-3,10-dione 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到1,4-二氢-1,4-甲桥蒽-9,10-二酮
  参考文献：
  名称：

  二碘化sa诱导的四环[10.2.n.0 2,11 .0 4,9 ] pentadeca-2,4,5,7,13-pentaene-3,10-diones的形成及相关体系

  摘要：

  内四环或外四环[10.2.n.0 2,11 .0 4,9 ]五环十烷基-4,5,7,13-四烯-3,10-二酮与Sml 2的反应导致有效形成氧化的标题醌。

  DOI：

  10.1016/0040-4039(94)02442-e

文献信息

• Rigid molecular racks featuring the 1,10-phenanthroline ligand especially those co-functionalised with redox-active groups or other bidentate ligands
  作者：Ronald N. Warrener、Austin C. Schultz、Mark A. Houghton、Douglas N. Butler

  DOI：10.1016/s0040-4020(97)00014-8

  日期：1997.3

  stereospecificity. Bridged 1,10-phenanthrolines with different separation distances and ligand, ligand orientations have been prepared and mixed ligand systems are described with diazafluorene and 3,6-di(2-pyridyl)pyridazine ligand components. New diad and triad systems are reported which contain redox-active components linked to ligand centres. The rigid nature of the polyalicyclic molrac framework and the fusion

  首次制备的6,7-二氮杂苯环酮（DAPC）以二聚体形式存在，但与单体11处于热平衡状态在解决方案中。DAPC是一种反应性二烯，可与具有高立体特异性的环应变和缺电子的二烯亲核体发生反应。制备了具有不同分离距离和配体的桥连的1,10-菲咯啉，配体的取向和混合的配体体系与二氮杂芴和3,6-二（2-吡啶基）哒嗪配体组成一起描述。据报道，新的二元组和三元组系统包含与配体中心相连的氧化还原活性成分。聚脂环莫拉克骨架的刚性性质和用于连接官能团的融合方法为分子提供了精确的生色团几何定位和取向。这使得这些系统成为研究电子转移和能量转移过程的关键分子。
• Rotational correlation times and radii of dithiazol-2-yl and dithiazolidin-2-yl free radicals
  作者：Shirley A. Fairhurst、Roger S. Pilkington、Leslie H. Sutcliffe

  DOI：10.1039/f19837900439

  日期：——

  2-dithiazolidin-2-yl radicals have been shown to be useful model compounds for detailed e.s.r. studies of rotational reorientation in liquid and frozen media. Consequently they are also potentially useful spin probes and spin labels. The e.s.r. powder spectra have been analysed and the resulting g and A tensors were used to calculate rotational diffusion correslation times, rotational energetics of activation

  已经证明，1,3,2-二噻唑-2-基和1,3,2-二噻唑烷-2-基是用于在液体和冷冻介质中进行旋转重取向的详细esr研究的有用的模型化合物。因此，它们也是潜在有用的自旋探针和自旋标记。对esr粉末光谱进行了分析，并将所得的g和A张量用于计算旋转扩散相关时间，激活的旋转能量和有效半径。后者比通过模型半径计算出的半径更接近匹配，而不是通过模型氮氧基自由基发现的：旋转扩散活化能表明，自由基的非极性特性使溶质与溶剂之间的相互作用最小化。
• Pd-Catalyzed C–H Annulation of Five-Membered Heteroaryl Halides with Norbornene Derivatives
  作者：Birakishore Padhi、Geunhee Kang、Eunmin Kim、Jeongmin Ha、Hyun Tae Kim、Jeewoo Lim、Jung Min Joo

  DOI：10.1021/acscatal.9b05177

  日期：2020.2.7

  Complementary to Catellani-type reactions and 1:1 coupling of six-membered halo(hetero)arenes and norbornene (NBE) derivatives, Pd-catalyzed 1:2 coupling of five-membered haloheteroarenes with NBEs was achieved to afford rigid nonplanar heterocycles. Pyrazole, thiophene, furan, and indole underwent exo- and trans-selective annulation. Two strained alkene groups of the resulting products were further

  互补于Catellani型反应和六元卤代（杂）芳烃与降冰片烯（NBE）衍生物的1：1偶联，Pd催化五元卤代芳烃与NBE的1：2偶联以提供刚性的非平面杂环。吡唑，噻吩，呋喃和吲哚进行了exo-和反选择环空。进一步处理所得产物的两个应变烯基，得到1-烷基吲唑和梯形聚合物。杂芳烃的类型和卤化物的位置以及配体和碱的选择对于在C–H环化反应和Catellani反应之间设置偏好至关重要，这对于开发Pd催化，NBE介导的杂芳烃反应非常有用。
• Oxidative Dehydrogenation and the Aromatization of Polycycles Using <i>o</i>-Iodoxybenzoic Acid (IBX)
  作者：Sambasivarao Kotha、Shaibal Banerjee、Kalyaneswar Mandal

  DOI：10.1055/s-2004-829580

  日期：——

  An efficient and convenient method for the dehydro­genation and aromatization of various polycycles using o-iodoxybenzoic acid (IBX) is described.

  本文介绍了一种利用邻碘氧基苯甲酸（IBX）对各种多环进行脱氢和芳香化的高效便捷方法。
• Diels; Alder, Chemische Berichte, 1929, vol. 62, p. 2357
  作者：Diels、Alder

  DOI：——

  日期：——