6-methoxy-2-methyl-9H-carbazole | 58400-37-6

• 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: 6-methoxy-2-methyl-9H-carbazole
• 英文别名: 6-methoxy-2-methylcarbazole；6-methoxy-2-methyl-carbazole；6-Methoxy-2-methyl-9H-carbazole
• CAS: 58400-37-6
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: NGNCTDCPIOVVOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  405.1±25.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(4-methoxyphenyl)-3-methylaniline 在 copper diacetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以83%的产率得到6-methoxy-2-methyl-9H-carbazole
  参考文献：
  名称：

  通过分子内 Pd 催化、微波辅助氧化联芳基偶联反应无酸合成咔唑和咔唑醌 - Murrayafoline A、2-Methoxy-3-methylcarbazole 和 Glycozolidine 的有效合成

  摘要：

  基于钯催化的微波辅助双 C-H 键活化过程，开发了一种在非酸性条件下由二芳基胺合成氧化咔唑的温和有效的方法。这一新协议已成功应用于三种天然咔唑的合成，即 murrayafoline A、2-甲氧基-3-甲基咔唑和糖唑烷。反应范围也扩大到包括苯并稠合咔唑醌的合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900537

文献信息

• A Tandem Reduction-Oxidation Protocol for the Conversion of 1-Keto-1,2,3,4-tetrahydrocarbazoles to Carbazoles via Tosylhydrazones through Microwave Assistance: Efficient Synthesis of Glycozoline, Clausenalene, Glycozolicine, and Deoxycarbazomycin B and th
  作者：Suchandra Chakraborty、Gautam Chattopadhyay、Chandan Saha

  DOI：10.1002/jhet.999

  日期：2013.1

  methodology for the synthesis of carbazoles from 1‐keto‐1,2,3,4‐tetrahydrocarbazoles via the corresponding tosylsulfonhydrazones by a one‐pot tandem reduction–oxidation protocol using a combination of NaBH4 and Pd–C on MgSO4·7H2O, a solid support, under microwave is developed. The reaction is successfully extended toward the synthesis of several naturally occurring carbazole alkaloids, namely 3‐methylcarbazole

  一种新颖高效的方法，通过NaBH 4和Pd-C的组合，通过一锅串联还原-氧化方案，通过相应的甲苯磺酰基hydr肼，通过相应的甲苯磺酰基hydr，由1-酮，1,2,3,4-四氢咔唑合成咔唑在微波作用下形成了4 ·7H 2 O（一种固体支持物）。该反应已成功地扩展到几种天然存在的咔唑生物碱的合成，即3-甲基咔唑，糖唑啉，黄嘌呤，糖唑啉，墨瑞福林A和脱氧咔唑霉素B（一种已知具有良好抗菌活性的咔唑衍生物）。
• Synthesis of Oxygenated Carbazoles by Palladium-Mediated Oxidative Double C-H Activation of Diarylamines Assisted by Microwave Irradiation
  作者：J. Menéndez、Vellaisamy Sridharan、Mª Martín

  DOI：10.1055/s-2006-950415

  日期：2006.9

  Microwave irradiation in the presence of palladium acetate and traces of dimethylformamide allows the fast and efficient cyclodehydrogenation of diphenylamines into carbazoles. The scope of the microwave-assisted reaction is broader than that of the one using conventional conditions in that it allows the preparation of oxygenated carbazoles without apparent loss in yield. The applicability of the method to the preparation of carbazole alkaloids has been demonstrated by the development of a total synthesis of ­murrayafoline A, which proceeds in 50% overall yield from commercially available materials and is the shortest and most efficient route for the preparation of this alkaloid to date.

  在有醋酸钯和微量二甲基甲酰胺的存在下进行微波照射，可以快速高效地将二苯胺环脱氢成卡巴唑。与传统条件下的反应相比，微波辅助反应的适用范围更广，因为它允许在产率几乎没有明显损失的情况下制备氧化卡巴唑。该方法在卡巴唑生物碱的制备中的适用性已经通过murrayafoline A的总合成得到了证明，该合成从市售材料出发，整体产率达到50%，是迄今为止制备该生物碱的最短和最高效的路线。
• Catalytic C-2 Allylation of Indoles by Electronic Modulation of the Indole Ring and its Application to the Synthesis of Functionalized Carbazoles
  作者：Ju Young Lee、Hyeri Ha、Seri Bae、Inhyuk Han、Jung Min Joo

  DOI：10.1002/adsc.201600568

  日期：2016.11.3

  We report a palladium‐catalyzed C‐2 allylation of indoles and subsequent cyclization of the allylated indoles. The electronic effects of chloro and ester groups that can be readily installed at the C‐3 position of indoles facilitated a highly efficient C–H allylation at the C‐2 position. The resulting 2‐allyl‐3‐chloroindoles were found to be suitable substrates for benzannulation reactions with alkynes

  我们报道了钯催化的吲哚的C-2烯丙基化以及随后的烯丙基化的吲哚的环化反应。可以容易地将吲哚的C-3位置安装的氯和酯基团的电子效应促进了C-2位置的高效C-H烯丙基化。发现生成的2烯丙基3氯吲哚是与炔烃和降冰片二烯作为乙炔合成子进行苯环化反应的合适底物。这种方法利用容易获得的吲哚，乙酸烯丙酯和降冰片二烯，可以快速获得复杂的咔唑。
• Acid-Free Synthesis of Carbazoles and Carbazolequinones by Intramolecular Pd-Catalyzed, Microwave-Assisted Oxidative Biaryl Coupling Reactions - Efficient Syntheses of Murrayafoline A, 2-Methoxy-3-methylcarbazole, and Glycozolidine
  作者：Vellaisamy Sridharan、M. Antonia Martín、J. Carlos Menéndez

  DOI：10.1002/ejoc.200900537

  日期：2009.9

  A mild and efficient methodology for the synthesis of oxygenated carbazoles from diarylamines under non-acidic conditions was developed, based on a palladium-catalyzed, microwave-assisted double C–H bond activation process. This new protocol was successfully applied to the synthesis of three naturally occurring carbazoles, namely murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine. The

  基于钯催化的微波辅助双 C-H 键活化过程，开发了一种在非酸性条件下由二芳基胺合成氧化咔唑的温和有效的方法。这一新协议已成功应用于三种天然咔唑的合成，即 murrayafoline A、2-甲氧基-3-甲基咔唑和糖唑烷。反应范围也扩大到包括苯并稠合咔唑醌的合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)