2,3,4,9-tetrahydro-7-methoxy-3-methyl-1H-carbazol-1-one | 32550-51-9

• 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: 2,3,4,9-tetrahydro-7-methoxy-3-methyl-1H-carbazol-1-one
• 英文别名: 7-methoxy-3-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one；7-methoxy-3-methyl-2,3,4,9-tetrahydro-carbazol-1-one；1,2,3,4-Tetrahydro-7-methoxy-3-methyl-1-oxo-9H-carbazol；7-methoxy-3-methyl-2,3,4,9-tetrahydrocarbazol-1-one
• CAS: 32550-51-9
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: TYNYIYAZAGJZAG-UHFFFAOYSA-N

物化性质

• 熔点：
  206-209 °C
• 沸点：
  419.1±40.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4,9-tetrahydro-7-methoxy-3-methyl-1H-carbazol-1-one 在 palladium on activated charcoal 作用下， 以 二苯醚 为溶剂， 反应 1.5h， 以6 g的产率得到1-羟基-7-甲氧基-3-甲基咔唑
  参考文献：
  名称：

  Ramesh, Kakarla; Kapil, R. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 462 - 465

  摘要：

  DOI：
• 作为产物：
  描述：

  tributyl(4-methoxy-2-nitrophenyl)stannane 在 二(氰基苯)二氯化钯 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ copper(l) iodide 、 三苯胂 、 一氧化碳 、 1,3-双(二苯基膦)丙烷 、 邻菲罗啉 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 80.0~90.0 ℃ 、607.95 kPa 条件下， 反应 120.0h， 生成 2,3,4,9-tetrahydro-7-methoxy-3-methyl-1H-carbazol-1-one
  参考文献：
  名称：

  Palladium-catalyzed syntheses of tetrahydrocarbazolones as advanced intermediates to carbazole alkaloids

  摘要：

  Two sequential palladium-catalyzed reactions, an intermolecular Stille cross-coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation, have been employed as the key synthetic steps toward six tetrahydrocarbazolones. The products are advanced intermediates toward a number of naturally occurring carbazole alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.100

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）。
• A novel CAN-SiO2-mediated one-pot oxidation of 1-keto-1,2,3,4-tetrahydrocarbazoles to carbazoloquinones: Efficient syntheses of murrayaquinone A and koeniginequinone A
  作者：Suchandra Chakraborty、Gautam Chattopadhyay、Chandan Saha

  DOI：10.1002/jhet.561

  日期：2011.3

  1‐keto‐1,2,3,4‐tetrahydrocarbazoles (1) to carbazole‐1,4‐quinones (2) are efficiently carried out by CAN‐SiO2‐mediated reaction. This generalized protocol was successfully extended to the synthesis of two naturally occurring carbazoloquinones: murrayaquinone A (2b) and koeniginequinone A (2g). A plausible mechanism for this novel reaction involves formation of a 9‐hydroxy‐2,3,4,9‐tetrahydro‐1H‐carbazole‐1‐one

  通过CAN-SiO 2介导的反应可以有效地将取代的1-酮-1,2,3,4-四氢咔唑（1）一锅法氧化为咔唑-1,4-醌（2）。该通用方案已成功扩展到两种天然存在的咔唑醌的合成：murrayaquinone A（2b）和koeniginequinone A（2g）。这种新反应的可能机制涉及形成9-羟基-2,3,4,9-四氢-1 H-咔唑-1-酮，然后重排为1-羟基咔唑衍生物，这些衍生物会被铈进一步氧化（IV ）到咔唑醌。J.杂环化​​学。（2011）。
• Carbazole alkaloids from Glycosmis pentaphylla
  作者：A. Chakraborty、B.K. Chowdhury、S.S. Jash、G.K. Biswas、S.K. Bhattacharyya、P. Bhattacharyya

  DOI：10.1016/0031-9422(92)83310-u

  日期：1992.7

  Abstract Three carbazole alkaloids, glycozolicine, 3-formyl carbazole and glycosinine, have been isolated from the roots of Glycosmis pentaphylla . The structures of glycozolicine and glycosinine have been established as 5-methoxy-3-methyl carbazole and 2-methoxy-3-formyl carbazole, respectively, from physical and chemical evidence, and synthesis.

  摘要 已从五叶糖衣的根中分离得到三种咔唑生物碱，即甘唑啉、3-甲酰咔唑和糖苷。根据物理和化学证据以及合成，糖唑啉和糖苷的结构已分别确定为 5-甲氧基-3-甲基咔唑和 2-甲氧基-3-甲酰基咔唑。
• Chakraborty, Suchandra; Chattopadhyay, Gautam; Saha, Chandan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 2, p. 201 - 206
  作者：Chakraborty, Suchandra、Chattopadhyay, Gautam、Saha, Chandan

  DOI：——

  日期：——
• Carbazoloquinones from Murraya koenigii
  作者：C. Saha、B.K. Chowdhury

  DOI：10.1016/s0031-9422(97)01135-7

  日期：1998.5

  Two new carbazole alkaloids designated as koenigine-quinone A and koenigine-quinone B were isolated from the alcoholic extract of the stem bark of Murraya koenigii and their structures were established as 7-methoxy-3-methylcarbazole-1,4-quinone and 6,7-dimethoxy-3-methylcarbazole-1,4-quinone, respectively, from spectral data and synthetic evidences. (C) 1998 Elsevier Science Ltd. All rights reserved.