9,10-dihydro-9,10-bis(hydroxymethyl)-9,10-ethanoanthracene-11,12-anhydride | 145100-44-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 9,10-dihydro-9,10-bis(hydroxymethyl)-9,10-ethanoanthracene-11,12-anhydride
• CAS: 145100-44-3
• 化学式: C₂₀H₁₆O₅
• 分子量: 336.344
• InChiKey: NDIWOHKEHIZIDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  9,10-二(氯甲基)蒽 生成 9,10-dihydro-9,10-bis(hydroxymethyl)-9,10-ethanoanthracene-11,12-anhydride
  参考文献：
  名称：

  The structure of 9,10-Dihydro-9,10-bis(hydroxymethyl)-9, 10-ethanoanthracene-11,12-anhydride

  摘要：

  The title compound, prepared as an intermediate in the synthesis of dibenzo[2.2.2.n]paddlanes, exhibits rapid conformational interconversion on the NMR timescale. The X-ray structure is reported and compared to molecular mechanics calculations. The results imply significant steric crowding in the title compound.

  DOI：

  10.1016/s0040-4039(00)60951-6

文献信息

• Solvent Influence on the Diels-Alder Reaction Rates of 9-(Hydroxymethyl)anthracene and 9,10-Bis(hydroxymethyl)anthracene with Two Maleimides
  作者：Vladimir D. Kiselev、Dmitry A. Kornilov、Igor A. Sedov、Alexander I. Konovalov

  DOI：10.1002/kin.21057

  日期：2017.1

  9‐(hydroxymethyl)anthracene and 9,10‐bis(hydroxymethyl)anthracene with maleic anhydride and two maleimides, N‐ethyl‐ and N‐phenylmaleimide, have been studied at various temperatures and pressures in different solvent media. A rate acceleration in water in comparison with organic solvents is observed. Thermodynamic functions of activation for the reaction of 9,10‐bis(hydroxymethyl)anthracene with N‐ethylmaleimide

  在不同温度和压力下，研究了9-（羟甲基）蒽和9,10-双（羟甲基）蒽与马来酸酐和两种马来酰亚胺N-乙基和N-苯基马来酰亚胺的Diels-Alder反应速率。不同的溶剂介质。与有机溶剂相比，观察到了水中的速率加速。活化的热力学函数，用于9,10-双（羟甲基）蒽与N的反应测定了1,4-二恶烷与水的二元混合物中的乙基马来酰亚胺。从观察到的趋势可以得出结论，在水中的狄尔斯-阿尔德反应的加速与反应物向活化复合物途中的反应中心的能量有利脱水有关。添加有机助溶剂会使这些中心的去溶剂化作用降低。
• Effect of hydrostatic pressure, temperature, and solvent on the rate of the Diels–Alder reaction between 9,10-anthracenedimethanol and maleic anhydride
  作者：V. D. Kiselev、D. A. Kornilov、O. V. Anikin、L. I. Latypova、A. I. Konovalov

  DOI：10.1134/s0036024417030128

  日期：2017.3

  of the reaction between 9,10-anthracenedimethanol and maleic anhydride in 1,4-dioxane, acetonitrile, trichloromethane, and toluene is studied at 25, 35, 45°C in the pressure range of 1–1772 bar. The rate constants, enthalpies, entropies and activation volumes are determined. It is shown that the rate of reaction with 9,10-anthracenedimethanol is approximately one order of magnitude higher than with

  在1,1772 bar的压力范围内，分别于25、35、45°C下研究了9,10-蒽二甲醇与马来酸酐在1,4-二恶烷，乙腈，三氯甲烷和甲苯中的反应速率。确定速率常数，焓，熵和活化体积。结果表明，与9，10-蒽二甲醇的反应速率比与9-蒽二甲醇的反应速率高约一个数量级。