9,10-dihydro-9,10-ethananthracenyl-11,12-dicarboxylic acid | 33216-00-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 9,10-dihydro-9,10-ethananthracenyl-11,12-dicarboxylic acid
• 英文别名: trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid；trans-(11S,12S)-(-)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid；(15S,16S)-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-dicarboxylic acid
• CAS: 33216-00-1
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: NYMGGONMSRTFKV-CKUJCDMFSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  556.0±50.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-9,10-ethananthracenyl-11,12-dicarboxylic acid 在 吡啶 、 氯化亚砜 、 碳酸氢钠 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  振动圆二色光谱中基于C * –H的模式和大幅度运动效应的重要性：富马酸二甲酯和蒽的手性加合物

  摘要：

  研究了基于C * –H的模式（C *为手性碳原子）以及大振幅运动在振动吸收（VA）和振动圆二色性（VCD）光谱中的作用。富马酸二甲酯与蒽的加合物实例，即二甲基-（+）-（11 R，12 R考虑了为此目的专门合成的）-9,10-二氢-9,10-乙基蒽-11,12-二羧酸酯及其两个氘代异位异构体。通过比较未氘代和氘代物种的实验光谱和DFT计算光谱，我们证明VA和VCD光谱中的C * –H弯曲，摇摆和拉伸模式在定义明确的光谱特征中清晰可见。此外，通过分析指纹和C–H拉伸区域的VA和VCD数据，可以收集有关构象异构体分布的重要信息，尤其要注意带状数据。通过执行线性跃迁（LT）计算，已模拟了与两个甲氧基部分的大幅度运动有关的效应，它包括系统地改变两个甲氧基部分的相对位置，并计算以此方式获得的部分优化结构的VCD光谱。与实验结果相比，LT方法可以提高计算光谱的质量，尤其是在相对强度和带宽方面。

  DOI：

  10.1021/jp502544v
• 作为产物：
  描述：

  (11S,12S)-9,10-ethane-11,12-dimenthyl carboxylate-9,10-dihydro anthracene 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以53%的产率得到9,10-dihydro-9,10-ethananthracenyl-11,12-dicarboxylic acid
  参考文献：
  名称：

  Enantioselective Diels-Alder reactions: novel constrained bis(oxazoline) ligand-metal triflate catalysts

  摘要：

  Five chiral 1,4-bis(oxazoline) ligands, each bearing a bicyclic backbone, were prepared and examined in Mg(OTf)(2)-, Zn(OTf)(2)-, and Cu(OTf)(2)-catalyzed Diels-Alder reactions. The cycloadditions were carried out at room temperature and afforded enantiomeric excess up to 88%. Surprisingly, a non-C-2-symmetric bis(oxazoline) bearing a meso backbone was among the more efficient ligands examined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00323-6

文献信息

• Synthesis and Effects on Chloroquine Susceptibility in <i>Plasmodium </i><i>f</i><i>alciparum </i>of a Series of New Dihydroanthracene Derivatives
  作者：Sandrine Alibert、Christiane Santelli-Rouvier、Bruno Pradines、Carole Houdoin、Daniel Parzy、Janina Karolak-Wojciechowska、Jacques Barbe

  DOI：10.1021/jm011046l

  日期：2002.7.1

  To suggest a mechanism of action for drugs capable to reverse the chloroquine resistance, a new set of 9,10-dihydro-9,10-ethano and ethenoanthracene derivatives was synthesized and compounds were tested with the aim to assess their effect on chloroquine susceptibility in Plasmodium falciparum resistant strains. With respect to this, reversal of resistance and change in drug accumulation were compared

  为了提出一种能够逆转氯喹耐药性的药物的作用机理，合成了一组新的9,10-二氢-9,10-乙醇和乙炔蒽衍生物，并对其进行了测试，目的是评估其对氯喹敏感性的影响。恶性疟原虫抗性菌株。对此，比较了耐药性的逆转和药物积累的变化。结构-活性关系和分子建模研究使得为逆转剂定义药效基团和提出与某些选定氨基酸相互作用的推定模型成为可能。
• Structural elucidation of bipyridine helicate complexes and their precursors by NMR spectroscopy
  作者：Rita Annunziata、Maurizio Benaglia、Antonino Famulari、Laura Raimondi

  DOI：10.1002/mrc.828

  日期：2001.6

  1H and 13C NMR assignments of bipyridine helicate complexes and their precursor ligands were achieved using gradient‐based homo‐ and hetero‐correlated 2D experiments. The observed trends in 1H and 13C chemical shift variations [Δδ(H) and Δδ(C)], on passing from the ligands to the complexes, are accounted for on the basis of MO evaluation of atomic charges. Copyright © 2001 John Wiley & Sons, Ltd.

  联吡啶螺旋配合物及其前体配体的 1H 和 13C NMR 归属是使用基于梯度的同相关和异相关 2D 实验实现的。观察到的 1H 和 13C 化学位移变化 [Δδ(H) 和 Δδ(C)] 从配体传递到配合物时的趋势是基于对原子电荷的 MO 评估来解释的。版权所有 © 2001 John Wiley & Sons, Ltd.
• Synthesis of novel aza-heterocyclic derivatives from diester and diacid chlorides having the dibenzobarrelene skeleton
  作者：İrfan Çapan、Süleyman Servi

  DOI：10.1080/00397911.2018.1437449

  日期：2018.5.19

  aza-heterocyclic-substituted dibenzobarrelene derivatives from the 2-aminobenzimidazole (or 2-aminoimidazoline) with diacid chlorides and diester in the presence of various organic bases, different products were isolated in high yield. NMR spectroscopic analysis proved these products to be dibenzobarrelene-substituted fused benzimidazodiazepine, imidazolinediazepine, and dicarboxamides derivatives. Cyclic

  摘要当试图在各种有机碱存在下从 2-氨基苯并咪唑（或 2-氨基咪唑啉）与二酰氯和二酯合成对称的氮杂杂环取代的二苯并芘衍生物时，不同的产物以高产率分离。NMR 光谱分析证明这些产物是二苯并茚取代的稠合苯并咪唑并二氮杂、咪唑啉二氮杂和二甲酰胺衍生物。使用这些方法首次合成了具有二苯并芘骨架的环状或非环状二甲酰胺。图形概要
• Singh, Ashok Kumar; Verma, Mamta; Verma, Shiva Mohan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 7, p. 631 - 634
  作者：Singh, Ashok Kumar、Verma, Mamta、Verma, Shiva Mohan

  DOI：——

  日期：——
• Chiral selectors based on C2-symmetric dicarboxylic acids
  作者：Stig Allenmark、Urban Skogsberg、Linda Thunberg

  DOI：10.1016/s0957-4166(00)00331-1

  日期：2000.9

  Bis-allylamides of rigid C-2-symmetric dicarboxylic acids, useful as precursors in the synthesis of liquid chromatographic chiral stationary phases via hydrosilylation reactions, have been prepared by two different approaches. One involved resolution of the dicarboxylic acid followed by reaction with allylamine via the acid chloride or by a carbodiimide-assisted condensation. The other route involved acetalization of N,N'-diallyl-L-tartardiamide (DATD) with aromatic aldehydes. Moreover, transformation of the enantiopure dicarboxylic acid used in the first route into the corresponding diamine permitted the synthesis of selectors possessing a reversed amide functionality. The enantiomer-discriminating properties of some of these selectors were studied by NMR. (C) 2000 Elsevier Science Ltd. All rights reserved.