dimethyl 9,10-dihydro-2,6-dihydroxy-9,10-ethenoanthracene-11,12-dicarboxylate | 106513-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: dimethyl 9,10-dihydro-2,6-dihydroxy-9,10-ethenoanthracene-11,12-dicarboxylate
• 英文别名: dimethyl (1S,8S)-4,11-dihydroxytetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9(14),10,12,15-heptaene-15,16-dicarboxylate
• CAS: 106513-50-2；116300-50-6；116300-51-7
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: SKIYOZMHZOONHU-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 9,10-dihydro-2,6-dihydroxy-9,10-ethenoanthracene-11,12-dicarboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 9,10-dihydro-2,6-dihydroxy-9,10-ethenoanthracene-11,12-dicarboxylic acid
  参考文献：
  名称：

  Synthesis of the altertoxin III framework

  摘要：

  The framework of altertoxin III, a mycotoxin produced by Alternaria fungi investing food and feed, has been synthesised for the first time. Synthetic schemes including Diels-Alder reactions of anthracene derivatives turned out to be not successful due to an aromatisation of key intermediates. This aromatisation was further investigated by DFT calculations, which showed that the aromatisation tendency is dependant from the electronic characteristics of attached substituents. A Friedel-Crafts-type hafnium triflate-catalysed dimerisation of dihydroxytetralins with subsequent benzylic oxidation furnished the target compound, which should be a suitable precursor for the synthesis of altertoxin III and related natural products. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.013
• 作为产物：
  描述：

  2,6-二羟基蒽醌 在 盐酸 、 ammonium hydroxide 、 aluminum amalgam 、 甲烷磺酸 、 二苯基二硒醚 、 potassium tert-butylate 、 氯化二乙基铝 、 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.08h， 生成 dimethyl 9,10-dihydro-2,6-dihydroxy-9,10-ethenoanthracene-11,12-dicarboxylate
  参考文献：
  名称：

  "Hydrophobic" binding of water-soluble guests by high-symmetry, chiral hosts. An electron-rich receptor site with a general affinity for quaternary ammonium compounds and electron-deficient .pi. systems

  摘要：

  DOI：

  10.1021/ja00228a036

文献信息

• Design and synthesis of a new class of hydrophobic binding sites
  作者：Michael A. Petti、Timothy J. Shepodd、Dennis A. Dougherty

  DOI：10.1016/s0040-4039(00)84106-4

  日期：1986.1

  The design, synthesis and basic aggregation and binding behavior of a new class of water-soluble molecules with hydrophobic binding sites are reported.

  报道了具有疏水性结合位点的新型水溶性分子的设计，合成，基本聚集和结合行为。
• "Hydrophobic" binding of water-soluble guests by high-symmetry, chiral hosts. An electron-rich receptor site with a general affinity for quaternary ammonium compounds and electron-deficient .pi. systems
  作者：Michael A. Petti、Timothy J. Shepodd、Richard E. Barrans、Dennis A. Dougherty

  DOI：10.1021/ja00228a036

  日期：1988.9
• Evidence for the Importance of Polarizability in Biomimetic Catalysis Involving Cyclophane Receptors
  作者：Sarah M. Ngola、Dennis A. Dougherty

  DOI：10.1021/jo960521y

  日期：1996.1.1

  Cyclophanes 1-6 catalyze the nucleophilic dealkylation of a simple sulfonium compound by potassium iodide. The cation-pi interaction is important in substrate binding, but the primarily electrostatic nature of this effect does not explain all observations concerning catalysis. As a series of substituents are placed on the cyclophane framework, a systematic variation in catalyst effectiveness is seen, such that more polarizable substituents produce more potent catalysts. This provides support for the notion that transition states are especially polarizable, and catalysis can be enhanced by maximizing London dispersion forces. The reactions studied here are very similar to the broad class of biological methylations mediated by S-adenosylmethionine, and the biological catalysts may use forces similar to those described here.
• An improved, two step synthesis of the chiral templating reagent 2,6-Dihydroxy-9,10-dihydro-11,12-dicarbomethoxyethenoanthracene
  作者：James C. Adrian、Tina M. Ovitt

  DOI：10.1016/0957-4166(96)00298-4

  日期：1996.8

  An improved, two step synthesis, of the importrant chiral templating reagent 2,6-Dihydroxy-9, 10-dihydro-11,12-dicarbomethoxyethenoanthracene 3 has been developed with an overall yield of 82% (not optimized). The reaction features a simple diastereomeric separation to afford the enantiomeric products. The reaction can be scaled up to afford multigram quantities of the ethenoanthracenes. Copyright (C) 1996 Elsevier Science Ltd
• Changing the size of a cavity via an electron-transfer: synthesis and reduction of 1,5,22,26-tetraoxa-[5,5]-(2,8)-dibenzo[a,e]cylooctatetraenophane
  作者：Willi Heinz、Hans-Joachim Räder、Klaus Müllen

  DOI：10.1016/s0040-4039(00)95146-3

  日期：1989.1