(9R,10R)-2,6-dihydroxy-9,10-dihydro-11,12-dicarbomethoxyethenoanthracene | 116300-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (9R,10R)-2,6-dihydroxy-9,10-dihydro-11,12-dicarbomethoxyethenoanthracene
• 英文别名: dimethyl (1R,8R)-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: 116300-51-7
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: SKIYOZMHZOONHU-HZPDHXFCSA-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：

  (9R,10R)-2,6-dihydroxy-9,10-dihydro-11,12-dicarbomethoxyethenoanthracene 在 cesium hydroxide 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 18.0h， 生成 2,6-bis(p-methylbenzyloxy)-9,10-dihydro-11,12-dicarboxyethenoanthracene
  参考文献：
  名称：

  Circular Dichroism Studies of Molecular Recognition with Cyclophane Hosts in Aqueous Media

  摘要：

  Circular dichroism (CD) methods have been employed to study molecular recognition phenomena in water soluble cyclophane hosts such as 1 and 2. The CD method is well suited to these systems and produces results that complement and expand upon previous NMR studies. The CD method operates at lower concentrations, allowing determinations of larger binding constants. Most importantly, when data concerning induced CD observed on binding achiral guests are analyzed using INDO/S coupled-oscillator calculations, valuable information concerning the binding conformations of the guest is obtained.

  DOI：

  10.1021/ja00141a014
• 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 (9R,10R)-2,6-dihydroxy-9,10-dihydro-11,12-dicarbomethoxyethenoanthracene
  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

• A Selective Receptor for Arginine Derivatives in Aqueous Media. Energetic Consequences of Salt Bridges That Are Highly Exposed to Water
  作者：Sarah M. Ngola、Patrick C. Kearney、Sandro Mecozzi、Keith Russell、Dennis A. Dougherty

  DOI：10.1021/ja982499r

  日期：1999.2.1

  Quantitative measures of salt-bridge-type interactions in a highly exposed aqueous environment have been obtained by modifying the well-studied cyclophane platform 1 to include carboxylates in close proximity to bound, cationic guests, producing hosts 2 and 3. Many guests show significantly enhanced binding to 2 and 3, but cations of the RNMe3+ type show little or no enhancement. We propose that the latter observations result from the fact that RNMe3+ compounds have very diffuse positive charges. Guests that show enhanced binding have focused regions of large, positive electrostatic potential. The highly charged 3 is able to bind very polar, very well-solvated guests, including a series of arginine-based dipeptides. Neutral, water-soluble host 4 was prepared and found to show a decreased affinity for cationic guests. We propose a novel induced dipole mechanism to rationalize these results.
• Kearney, Patrick C.; Mizoue, Laura S.; Kumpf, Robert A., Journal of the American Chemical Society, 1993, vol. 115, # 22, p. 9907 - 9919
  作者：Kearney, Patrick C.、Mizoue, Laura S.、Kumpf, Robert A.、Forman, Jonathan E.、McCurdy, Alison、Dougherty, Dennis A.

  DOI：——

  日期：——
• 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
• "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
• Circular Dichroism Studies of Molecular Recognition with Cyclophane Hosts in Aqueous Media
  作者：Jonathan E. Forman、Richard E. Barrans、Dennis A. Dougherty

  DOI：10.1021/ja00141a014

  日期：1995.9

  Circular dichroism (CD) methods have been employed to study molecular recognition phenomena in water soluble cyclophane hosts such as 1 and 2. The CD method is well suited to these systems and produces results that complement and expand upon previous NMR studies. The CD method operates at lower concentrations, allowing determinations of larger binding constants. Most importantly, when data concerning induced CD observed on binding achiral guests are analyzed using INDO/S coupled-oscillator calculations, valuable information concerning the binding conformations of the guest is obtained.