5,8-dimethoxy-1,4-methano-1,2,3,4-tetrahydronaphthalene | 25715-49-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5,8-dimethoxy-1,4-methano-1,2,3,4-tetrahydronaphthalene
• 英文别名: 1,4-dimethoxy-5,8-methano-5,6,7,8-tetrahydronaphthalene；1.4-Dimethoxy-5.8-methano-6.7-dihydronaphthalin；3'.6'-Dimethoxybenzonorbornylen；3,6-Dimethoxytricyclo[6.2.1.02,7]undeca-2,4,6-triene
• CAS: 25715-49-5
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: AVFMKSMSBDQAAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  288.9±40.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,8-dimethoxy-1,4-methano-1,2,3,4-tetrahydronaphthalene 在 三溴化硼 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 5,8-dihydroxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carboxaldehyde
  参考文献：
  名称：

  2,4-Dialkyl-8,9,10,11-tetrahydrobenzo[g]pyrimido[4,5-c]isoquinoline-1,3,7,12(2H,4H)-tetraones as new leads against Mycobacterium tuberculosis

  摘要：

  Given the re-emergence of tuberculosis in Europe and beyond, the search for novel bio-active compound classes against this disease is of utmost importance. As a result of a high intrinsic tolerance of the etiological agent, Mycobacterium tuberculosis, towards most antibiotics and xenobiotics, the search for such new compounds is far from trivial. Further exacerbated by the rapid generation and spread of drug resistant M. tuberculosis and fuelled by the HIV/AIDS pandemic, halting the tuberculosis epidemic is of paramount importance. As part of our program to design new 2-aza-anthraquinones with anti-mycobacterial activity, various dialkyltetrahydrobenzo[g]pyrimido[4,5-c]lisoquinolinetetraones were designed and synthesised. The compounds were submitted to a biological evaluation in which the activity against M.tb H37Rv(lux) was observed, as well as the acute toxicity towards J774 A.1 macrophages. From these results, the selectivity index was calculated. Furthermore, the activity of the most promising compounds was further studied against a multi-drug resistant LAM-1 strain and against intracellular replicating M.tb. The study was further extended with a comet assay and a VITOTOX (TM) assay to investigate the possibility of observable genotoxic effects caused by these compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.024
• 作为产物：
  描述：

  3',6'-二羟基苯并降冰片烯 生成 5,8-dimethoxy-1,4-methano-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  对苯二酚与二氧化氮的选择性硝化与氧化脱烷基

  摘要：

  各种烷基取代的对二烷氧基苯（ArH）可以通过硝化（ArNO 2）或氧化脱烷基化成醌（Q）与二氯甲烷溶液中的二氧化氮（NO 2）反应。光谱瞬变指示来自二烷氧基苯自由基阳离子这些耦合过程（ARH +·形成为从disproprtionated前体电子转移常见的反应中间体）ARH，NO + ] N0 3 - 。在快速的后续步骤中。ARH +·经历均裂耦合与NO 2（这会导致芳烃硝化）和NO的亲核攻击3 -（这导致氧化脱烷基）。这样，通过溶剂极性和添加的硝酸盐可以有效地调节硝化和氧化脱烷基之间的竞争。

  DOI：

  10.1016/s0040-4020(01)81329-6

文献信息

• Intervalence (Charge-Resonance) Transitions in Organic Mixed-Valence Systems. Through-Space versus Through-Bond Electron Transfer between Bridged Aromatic (Redox) Centers
  作者：D.-L. Sun、S. V. Rosokha、S. V. Lindeman、J. K. Kochi

  DOI：10.1021/ja037867s

  日期：2003.12.1

  intramolecular electron transfer is enforced in the mixed-valence cation radical 2a(*)(+) by the p-phenylene bridge which provides the structurally inflexible and linear connection between Ar(*)(+)/Ar redox centers. The direct comparison of intramolecular rates of electron transfer (k(ET)) between identical T(*)(+)/T centers in 3(*)(+) and 2a(*)(+)( )()indicates that through-space and through-bond mechanisms

  在包含一对芳香族氧化还原中心 (Ar(*)(+)/Ar) 的混合价系统的电子光谱中，一致地观察到诊断性近红外区域中出现的区间吸收带，这些中心由两种基本不同类型的分子桥。分子内电子转移的空间通路由混合价阳离子自由基 3(*)(+) 中的邻二甲苯桥决定，其中 Ar = 2,5-二甲氧基-对甲苯基 (T)，其中构象流动性允许平面 T(*)(+)/T 氧化还原中心的近端顺式配置。四个独立的实验探针通过测量（a）循环伏安图中相当大的电位分裂，表明这种共面 Ar(*)(+)/Ar 氧化还原中心之间存在较大的空间电子相互作用，(b) X 射线晶体学对 T(*)(+)/T 中心的醌式畸变，(c) ESR 超精细分裂的“加倍”，以及 (d) 明显的间隔电荷共振带。在混合价阳离子自由基 2a(*)(+) 中，分子内电子转移的直通 (br)-键通路由对亚苯基桥强制执行，该桥在 Ar(*)(+) 之间提供结构上不灵活的线性连接/Ar
• Bicyclic aromatic compounds, a process for their preparation and their
  申请人：L'Oreal

  公开号：US04898864A1

  公开（公告）日：1990-02-06

  Bicyclic aromatic compound having the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen or alkyl, at least two of R.sub.1 -R.sub.4 radicals being other than hydrogen, A represents methylene or dimethylene; when A represents dimethylene, R.sub.1 and R.sub.3 together can form a methylene or dimethylene radical, R.sub.5 and R.sub.6 represent hydrogen, halogen, lower alkyl, lower alkoxy or hydroxy, R' represents hydrogen, hydroxy, alkoxy, C.sub.1 -C.sub.4 cicyloxy or amino, R" represents hydrogen or lower alkoxy, or R' and R" together form an oxo, methano or hydroxyimino radical, B represents cyclohexyl, cyclohexenyl, cyclohexadienyl or phenyl, substituted or not, R represents --CH.sub.2 OH or --COR.sub.7, R.sub.7 represents hydrogen, --OR.sub.8 or ##STR2## R.sub.8 represents hydrogen, C.sub.1 -C.sub.20 alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl, aralkyl or a sugar residue. r' and r" represent hydrogen, alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or benzyl, the residue of an amino acid or an aminated sugar, or taken together form a heterocycle, and the salts of the compound of formula I and their optical isomers as well as the tautomeric forms of the compounds of formula I with the exception of 2-[(5,8-methano-5,6,7,8-tetrahydro-2-naphthyl) carbonyl] benzoic acid. The compounds are useful in the treatment of the hair and skin having an oily appearance.

  具有以下结构式的双环芳香化合物：其中R.sub.1、R.sub.2、R.sub.3和R.sub.4代表氢或烷基，至少两个R.sub.1 -R.sub.4基团不是氢，A代表亚甲基或二亚甲基；当A代表二亚甲基时，R.sub.1和R.sub.3可以共同形成一个亚甲基或二亚甲基基团，R.sub.5和R.sub.6代表氢、卤素、低烷基、低烷氧基或羟基，R'代表氢、羟基、烷氧基、C.sub.1 -C.sub.4环氧基或氨基，R"代表氢或低烷氧基，或者R'和R"共同形成一个氧代、甲基或羟基亚胺基团，B代表环己基、环己烯基、环己二烯基或苯基，取代或不取代，R代表--CH.sub.2 OH或--COR.sub.7，R.sub.7代表氢、--OR.sub.8或R.sub.8代表氢、C.sub.1 -C.sub.20烷基、单羟基烷基、多羟基烷基、芳基、芳基烷基或糖残基。r'和r"代表氢、烷基、单羟基烷基、多羟基烷基、芳基或苄基，氨基酸残基或氨基化糖残基，或共同形成杂环，以及公式I化合物及其光学异构体的盐，以及除了2-[(5,8-甲基-5,6,7,8-四氢-2-萘基)羰基]苯甲酸之外的化合物的互变异构体。这些化合物在治疗具有油性外观的头发和皮肤方面具有用途。
• Asymmetric Induction in Ruthenium-Catalyzed[2+2] Cycloadditions between Bicyclic Alkenes and a Chiral Acetylenic Acyl Sultam
  作者：Karine Villeneuve、William Tam

  DOI：10.1002/anie.200352555

  日期：2004.1.23
• Intramolecular excitation transfer in 1,4-dimethoxy-5,8-methano-6,7-exo-[fluorene-9'-spiro-1"-cyclopropane]naphthalene
  作者：Angelo A. Lamola

  DOI：10.1021/ja01045a035

  日期：1969.8
• Rathore R., Bosch E., Kochi J. K., Tetrahedron, 50 (1994) N 23, S 6727- 6758
  作者：Rathore R., Bosch E., Kochi J. K.

  DOI：——

  日期：——