11-methoxy-12H-benzo[a]xanthen-12-one | 1452922-08-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 11-methoxy-12H-benzo[a]xanthen-12-one
• 英文别名: 11-methoxybenzo[a]xanthen-12-one
• CAS: 1452922-08-5
• 化学式: C₁₈H₁₂O₃
• 分子量: 276.291
• InChiKey: CKDQZNJNYIJZNR-UHFFFAOYSA-N

物化性质

• 熔点：
  198-201 °C
• 沸点：
  481.5±34.0 °C(predicted)
• 密度：
  1.304±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-methoxy-12H-benzo[a]xanthen-12-one 在 platinum(IV) oxide 、 正丁基锂 、 氢气 、 硝酸 作用下， 以 N-甲基吡咯烷酮 、 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 3.5h， 生成 8,10-diamino-7,11-dipropyl-7,11-dihydrobenzo[a]benzo[5,6]quinolino[2,3,4-kl]acridin-17c-ylium tetrafluoroborate
  参考文献：
  名称：

  阳离子[6] Helicenes的模块合成，正交后功能化，吸收和手性

  摘要：

  挑选：新型的阳离子二氮杂，氮杂氧和二氧杂[6]螺旋烯很容易制备，并通过正交的芳香亲电和替代亲核取代基选择性地官能化（请参阅方案）。还原，交叉偶联或缩合反应会引入额外的多样性，并允许调节吸收特性直至近红外区域。diaza盐可以拆分成单一对映体。

  DOI：

  10.1002/anie.201208926
• 作为产物：
  描述：

  2,6-二甲氧基苯甲酸 在 氯化亚砜 、 三溴化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.0h， 生成 11-methoxy-12H-benzo[a]xanthen-12-one
  参考文献：
  名称：

  Extended Triangulenium Ions: Syntheses and Characterization of Benzo-Bridged Dioxa- and Diazatriangulenium Dyes

  摘要：

  The very limited class of fluorophores, with a long fluorescence lifetime (>10 ns) and fluorescence beyond 550 nm, has been expanded with two benzo-fused triangulenium derivatives and two cationic [5]-helicene salts. The syntheses of the benzo-bridged dioxa- and diazatriangulenium derivatives (BDOTA(+) and BDATA(+), respectively) required two different synthetic approaches, which reflect the structural and physiochemical impact on the reactivity of [5]-helicenium precursors. Spectroscopic investigations show that the introduction of the benzo bridge into the triangulenium chromophore significantly redshifts the absorption and emission while maintaining fluorescence lifetimes above 10 ns. The combination of a high quantum yield, long fluorescence lifetime, and emission above 600 nm is possible only if the structural aspects of the triangulenium framework are perfectly harmonized to secure a low rate of nonradiative deactivation. The new benzo bridge may be a general motif to obtain red-shifted derivatives of other dye classes.

  DOI：

  10.1021/acs.joc.8b02978

文献信息

• Modular Synthesis, Orthogonal Post-Functionalization, Absorption, and Chiroptical Properties of Cationic [6]Helicenes
  作者：Franck Torricelli、Johann Bosson、Céline Besnard、Mahshid Chekini、Thomas Bürgi、Jérôme Lacour

  DOI：10.1002/anie.201208926

  日期：2013.2.4

  Pick and choose: Novel cationic diaza‐, azaoxo‐, and dioxo[6]helicenes are readily prepared and functionalized selectively by orthogonal aromatic electrophilic and vicarious nucleophilic substitutions (see scheme). Reductions, cross‐coupling, or condensation reactions introduce additional diversity and allow tuning of the absorption properties up to the near‐infrared region. The diaza salts can be

  挑选：新型的阳离子二氮杂，氮杂氧和二氧杂[6]螺旋烯很容易制备，并通过正交的芳香亲电和替代亲核取代基选择性地官能化（请参阅方案）。还原，交叉偶联或缩合反应会引入额外的多样性，并允许调节吸收特性直至近红外区域。diaza盐可以拆分成单一对映体。
• QUINOLINE, NAPHTHALENE AND CONFORMATIONALLY CONSTRAINED QUINOLINE OR NAPHTHALENE DERIVATIVES AS ANTI-MYCOBACTERIAL AGENTS
  申请人：Chattopadhyaya Jyoti

  公开号：US20110059948A1

  公开（公告）日：2011-03-10

  The invention relates to a compound of general formula I, II, III, IV, V, VI, VII, VIII, IX, X or a tautomer and the stereochemically isomeric forms thereof or pharmaceutically acceptable salts thereof, a N-oxide form thereof or a pro-drug thereof. The compound is usable as a medicament for the treatment of mycobacterial disease.

  本发明涉及一种符合以下公式I、II、III、IV、V、VI、VII、VIII、IX、X或其互变异构体，或其药学上可接受的盐、N-氧化物形式或前药的化合物。该化合物可用作治疗分枝杆菌病的药物。
• 12H-BENZO[b]XANTHEN-12-ONES, COMPOSITIONS CONTAINING, AND USES OF, SAME
  申请人：Beeley Nigel Robert Arnold

  公开号：US20180185325A1

  公开（公告）日：2018-07-05

  The present invention provides compounds of the following structure, methods of using such compounds, and pharmaceutical compositions containing such compounds. In addition, this invention provides methods for the treatment and/or prevention of disease states mediated by Aryl Hydrocarbon receptor pathways.
• Physicochemical and Electronic Properties of Cationic [6]Helicenes: from Chemical and Electrochemical Stabilities to Far-Red (Polarized) Luminescence
  作者：Johann Bosson、Geraldine M. Labrador、Simon Pascal、François-Alexandre Miannay、Oleksandr Yushchenko、Haidong Li、Laurent Bouffier、Neso Sojic、Roberto C. Tovar、Gilles Muller、Denis Jacquemin、Adèle D. Laurent、Boris Le Guennic、Eric Vauthey、Jérôme Lacour

  DOI：10.1002/chem.201603591

  日期：2016.12.19

  at 658 nm) are observed. The triplet quantum yields and circularly polarized luminescence are also reported. Finally, fine tuning of the optical properties of the diaza [6]helicene core is achieved through selective and orthogonal post‐functionalization reactions (12 examples, compounds 4–15). The electronic absorption is modulated from the orange to the far‐red spectral range (560–731 nm), and fluorescence

  阳离子二氧杂 ( 1 )、氮杂氧 ( 2 )和二氮杂 ( 3 ) [ 6 ]螺烯的物理化学性质表明， 与其 azaoxa 2 (p K R + =15.2, =−0.45 V) 和 dioxa 1 (p K R + =8.8, =−0.12 V) 类似物。这些阳离子发色团的荧光已建立，范围从橙色到远红色区域。从1到3，观察到最低能量跃迁（在乙腈中高达 614 nm）的红移以及荧光量子产率和寿命的增强（在 658 nm 处分别高达 31% 和 9.8 ns）。还报道了三重态量子产率和圆偏振发光。最后，通过选择性和正交的后官能化反应实现了二氮杂[6]螺旋烯核光学性质的微调（12 个示例，化合物4 – 15）。电子吸收从橙色到远红光谱范围（560-731 nm）进行调制，在 591 至 755 nm 范围内观察到荧光，量子效率高达 70%（619 nm）。通过第一原理计算合理化了外围助色取代基的影响。
• Extended Triangulenium Ions: Syntheses and Characterization of Benzo-Bridged Dioxa- and Diazatriangulenium Dyes
  作者：Martin Rosenberg、Marco Santella、Sidsel A. Bogh、Alberto Viñas Muñoz、Helene O. B. Andersen、Ole Hammerich、Ilkay Bora、Kasper Lincke、Bo W. Laursen

  DOI：10.1021/acs.joc.8b02978

  日期：2019.3.1

  The very limited class of fluorophores, with a long fluorescence lifetime (>10 ns) and fluorescence beyond 550 nm, has been expanded with two benzo-fused triangulenium derivatives and two cationic [5]-helicene salts. The syntheses of the benzo-bridged dioxa- and diazatriangulenium derivatives (BDOTA(+) and BDATA(+), respectively) required two different synthetic approaches, which reflect the structural and physiochemical impact on the reactivity of [5]-helicenium precursors. Spectroscopic investigations show that the introduction of the benzo bridge into the triangulenium chromophore significantly redshifts the absorption and emission while maintaining fluorescence lifetimes above 10 ns. The combination of a high quantum yield, long fluorescence lifetime, and emission above 600 nm is possible only if the structural aspects of the triangulenium framework are perfectly harmonized to secure a low rate of nonradiative deactivation. The new benzo bridge may be a general motif to obtain red-shifted derivatives of other dye classes.