1-methoxy-7-methyl-9H-carbazole | 73910-80-2

• 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: 1-methoxy-7-methyl-9H-carbazole
• CAS: 73910-80-2
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: QCYMBMCHAWDNRJ-UHFFFAOYSA-N

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：

  2-methoxy-N-(3-tolyl)aniline 在 copper diacetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 以72%的产率得到1-methoxy-7-methyl-9H-carbazole
  参考文献：
  名称：

  Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids

  摘要：

  An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.

  DOI：

  10.1055/s-0032-1317175

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）。
• Palladium-Catalyzed Direct Arylation-Based Domino Synthesis of Annulated N-Heterocycles Using Alkenyl or (Hetero)Aryl 1,2-Dihalides
  作者：Lutz Ackermann、Andreas Althammer、Peter Mayer

  DOI：10.1055/s-0029-1216977

  日期：2009.10

  A palladium-catalyzed reaction sequence consisting of an intermolecular amination and an intramolecular direct arylation enabled highly regioselective syntheses of functionalized indoles or carbazoles and proved to be amenable to the use of inexpensive 1,2-dichloroarenes as electrophiles. arylation - catalysis - heterocycles - palladium - sequential reaction

  由分子间胺化和分子内直接芳基化组成的钯催化的反应序列能够高度区域选择性地合成官能化的吲哚或咔唑，并被证明适合使用廉价的1,2-二氯芳烃作为亲电子试剂。 芳基化-催化-杂环-钯-顺序反应
• Domino NH/CH Bond Activation: Palladium-Catalyzed Synthesis of Annulated Heterocycles Using Dichloro(hetero)arenes
  作者：Lutz Ackermann、Andreas Althammer

  DOI：10.1002/anie.200603833

  日期：2007.2.26
• Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids
  作者：Joaquín Tamariz、Rafael Bautista、Alberto Jerezano

  DOI：10.1055/s-0032-1317175

  日期：——

  An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.