bismurrayaquinone A | 155519-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: bismurrayaquinone A
• 英文别名: rac-bismurrayaquinone A；3-methyl-2-(3-methyl-1,4-dioxo-9H-carbazol-2-yl)-9H-carbazole-1,4-dione
• CAS: 155519-86-1
• 化学式: C₂₆H₁₆N₂O₄
• 分子量: 420.424
• InChiKey: FKJFKIPTKQPIFB-UHFFFAOYSA-N

物化性质

• 沸点：
  656.5±55.0 °C(Predicted)
• 密度：
  1.525±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bismurrayaquinone A 生成 (P)-bismurrayaquinone A
  参考文献：
  名称：

  Bismurrayaquinone A: Synthesis, chromatographic enantiomer resolution, and stereoanalysis by computational and experimental CD Investigations

  摘要：

  The first total synthesis of a naturally occurring dimeric carbazole alkaloid, bismurrayaquinone A (4), is described, by oxidation of dimeric O-demethylmurrayafoline A, a still hypothetic natural product recently synthesized. By chromatography on a chiral phase, the two atropoenantiomers were separated. The absolute configurations of these two rotational isomers were elucidated by comparison of their calculated spectra with those measured experimentally.

  DOI：

  10.1016/0040-4020(95)00528-g
• 作为产物：
  描述：

  在 copper diacetate 、 palladium diacetate 、 溶剂黄146 作用下， 反应 12.0h， 以65%的产率得到bismurrayaquinone A
  参考文献：
  名称：

  BisMurrayaquinone A 对映选择性全合成及构型稳定性研究

  摘要：

  旋转丢失：双Murrayaquinone A 的第一个对映选择性全合成的简明策略利用无痕立体化学交换形成对映体富集的联苯核心，并以双向方式与天然产物进行精制。在一条不成功的初始路线上观察到的外消旋作用促使人们对双醌 A 和相关联醌的构型稳定性进行了研究。

  DOI：

  10.1002/anie.201104726

文献信息

• Palladium‐Catalyzed Regioselective Synthesis of 1‐Hydroxycarbazoles Under Aerobic Conditions
  作者：So Won Youn、Young Ho Kim、Yoon Hyung Jo

  DOI：10.1002/adsc.201801265

  日期：2019.2

  A palladium‐catalyzed aerobic C−H amidation of N‐Ts‐2‐amino‐3′‐hydroxylbiaryls has been developed to afford a diverse range of 1‐hydroxycarbazoles with high regioselectivity and efficiency. This protocol benefits from operational simplicity, robustness, and sustainability with the use of ambient air as the sole terminal oxidant. Further elaboration of the products obtained from this process provides

  已开发出钯催化的N -Ts-2-氨基-3'-羟基联芳基的好氧CH H酰胺化反应，以提供具有高区域选择性和效率的各种1-羟基咔唑。通过使用环境空气作为唯一的终端氧化剂，该协议得益于操作简便，稳健性和可持续性。从该方法获得的产物的进一步精制提供了容易获得各种咔唑生物碱的方法，包括咔唑醌和双咔唑。提出了一种机制，涉及在2-氨基-3'-羟基联芳基的更受空间阻碍的C2'-位置的双指导基团辅助区域选择性CH活化。
• Antiplasmodial Activity of Mono- and Dimeric Carbazoles
  作者：Gerhard Bringmann、Alfons Ledermann、Jörg Holenz、Muh-Tsuen Kao、Ulrich Busse、Howard Wu、Guido François

  DOI：10.1055/s-2006-957366

  日期：1998.2

  A series of mono-and dimeric natural and structurally modified carbazoles has been tested for activity against Plasmodium falciparum. One of the monomers, the synthetic compound 1,4-diacetoxy-3-methylcarbazole (17), displays the highest activity, with an IC50 value of 1.79 µg/ml. It is distinctly more active than the as yet best natural compound, 1-hydroxy-3-methylcarbazole (4) (4).

  我们测试了一系列单体和二聚体天然咔唑和结构修饰咔唑对恶性疟原虫的活性。其中一种单体，即合成化合物 1,4-二乙酰氧基-3-甲基咔唑（17）显示出最高的活性，IC50 值为 1.79 µg/ml。它的活性明显高于目前最好的天然化合物 1-羟基-3-甲基咔唑（4）（4）。
• Murphy, William S.; Bertrand, Martial, Journal of the Chemical Society. Perkin transactions I, 1998, # 24, p. 4115 - 4119
  作者：Murphy, William S.、Bertrand, Martial

  DOI：——

  日期：——
• Bismurrayaquinone A: Synthesis, chromatographic enantiomer resolution, and stereoanalysis by computational and experimental CD Investigations
  作者：Gerhard Bringmann、Alfons Ledermann、Martin Stahl、Klaus—Peter Gulden

  DOI：10.1016/0040-4020(95)00528-g

  日期：1995.8

  The first total synthesis of a naturally occurring dimeric carbazole alkaloid, bismurrayaquinone A (4), is described, by oxidation of dimeric O-demethylmurrayafoline A, a still hypothetic natural product recently synthesized. By chromatography on a chiral phase, the two atropoenantiomers were separated. The absolute configurations of these two rotational isomers were elucidated by comparison of their calculated spectra with those measured experimentally.
• Enantioselective Total Synthesis and Studies into the Configurational Stability of Bismurrayaquinone A
  作者：Leah C. Konkol、Fenghai Guo、Amy A. Sarjeant、Regan J. Thomson

  DOI：10.1002/anie.201104726

  日期：2011.10.10

  concise strategy of the first enantioselective total synthesis of bismurrayaquinone A utilized traceless stereochemical exchange to form an enantioenriched biphenyl core that was elaborated in a bidirectional manner to the natural product. Observed racemization on an unsuccessful initial route prompted studies into the configurational stability of bismurrayaquinone A and related biquinones.

  旋转丢失：双Murrayaquinone A 的第一个对映选择性全合成的简明策略利用无痕立体化学交换形成对映体富集的联苯核心，并以双向方式与天然产物进行精制。在一条不成功的初始路线上观察到的外消旋作用促使人们对双醌 A 和相关联醌的构型稳定性进行了研究。