6-hydroxy-2-methoxy-3-methyl-9H-carbazole | 58005-42-8

• 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-hydroxy-2-methoxy-3-methyl-9H-carbazole
• 英文别名: glycozolidal；glycozolidol；7-Methoxy-6-methyl-9H-carbazol-3-ol
• CAS: 58005-42-8
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: VSFAXCAPDWNRJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2-methoxy-3-methyl-9H-carbazole 在 锌 作用下， 反应 2.0h， 生成 3-甲基咔唑
  参考文献：
  名称：

  Glycozolidol，一种来自 Glycosmis pentaphylla 的抗菌咔唑生物碱

  摘要：

  摘要 Glycozolidol 是一种新型咔唑生物碱，是从五叶糖衣的根中分离得到的。根据物理和化学证据确定其结构为6-羟基-2-甲氧基-3-甲基咔唑。已发现该化合物对某些革兰氏阳性和革兰氏阴性细菌具有活性。

  DOI：

  10.1016/s0031-9422(00)84922-5
• 作为产物：
  描述：

  (4-溴苯氧基)(2-甲基-2-丙基)二苯基硅烷 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 、 copper diacetate 、 palladium diacetate 、 N,N-二甲基甲酰胺 、 sodium t-butanolate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.08h， 生成 6-hydroxy-2-methoxy-3-methyl-9H-carbazole
  参考文献：
  名称：

  Synthesis of the Pyrano[3,2-a]carbazole Alkaloids Koenine, Koenimbine, Koenigine, Koenigicine, and Structural Reassignment of Mukonicine

  摘要：

  Using the palladium(II)-catalyzed oxidative cyclization of a diarylamine and the annulation of a dimethylpyran ring by Lewis acid promoted reaction with prenal as key steps, the total syntheses of the 6-oxygenated pyrano[3,2-a]carbazole alkaloids koenine and koenimbine, and of the 6,7-dioxygenated pyrano[3,2-a]carbazole alkaloids koenigine and koenigicine (koenimbidine, koenidine) were achieved. Moreover, these studies led to an improved synthetic route to the 2,6-dioxygenated carbazole alkaloid glycozolidol. Mukonicine, originally published as 6,8-dimethoxypyrano[3,2-a]carbazole, was found to be identical with koenigicine.

  DOI：

  10.1055/s-0035-1560359

文献信息

• Transition Metals in Organic Synthesis, Part 91:¹ Palladium-Catalyzed Approach to 2,6-Dioxygenated Carbazole Alkaloids - First Total Synthesis of the Phytoalexin Carbalexin C
  作者：Hans-Joachim Knölker、Marika Schmidt

  DOI：10.1055/s-0029-1217810

  日期：2009.9

  The palladium(0)-catalyzed C-N bond formation and palladium(II)-catalyzed oxidative cyclization provide an efficient route to a series of 2,6-dioxygenated carbazole alkaloids including the first total synthesis of the phytoalexin carbalexin C.

  钯 (0) 催化的 CN 键形成和钯 (II) 催化的氧化环化为一系列 2,6-二氧化咔唑生物碱提供了有效途径，包括植物抗毒素卡巴莱辛 C 的首次全合成。
• 10.1021/acs.orglett.4c01352
  作者：Berlin, Cameron B.、Roenfanz, Hanna F.、Salwen, Madeleine、Nehete, Sai、Kozlowski, Marisa C.

  DOI：10.1021/acs.orglett.4c01352

  日期：——

  The first total syntheses of glycoborinine, clausenawalline A, and clausenawalline E were achieved. The key step employed a vanadium-catalyzed oxidative coupling of two hydroxycarbazole monomers. High-throughput experimentation was used to identify conditions favoring selective heterocoupling of these monomers that possess similar redox potentials. A combination of a vanadium catalyst and 4-acetamido-TEMPO

  首次实现了糖硼蛋白、黄皮蛋白 A 和黄皮蛋白 E 的全合成。关键步骤采用钒催化的两个羟基咔唑单体的氧化偶联。高通量实验用于确定有利于这些具有相似氧化还原电位的单体选择性杂偶联的条件。相对于单独的钒催化剂，钒催化剂和4-乙酰氨基-TEMPO的组合大大提高了交叉选择性。发现了选择性形成同二聚体黄皮蛋白A或异二聚体黄皮蛋白E作为主要产物的条件。
• PREVENTION AND TREATMENT OF INFLAMMATORY CONDITIONS
  申请人：GLYCOREGIMMUNE, INC.

  公开号：US20160158258A1

  公开（公告）日：2016-06-09

  In accordance with some embodiments herein, methods and compositions for prevention and treatment of inflammatory conditions are provided. In some embodiments, compositions comprising NKT-2 activators, for example miltefosine are provided. In some embodiments, the compositions further comprise sulfatide and/or a RAR agonist. In some embodiments, the compositions comprise activators of Type II NKT cells, and/or inhibitors of Type I NKT cells.
• Synthesis of the Pyrano[3,2-a]carbazole Alkaloids Koenine, Koenimbine, Koenigine, Koenigicine, and Structural Reassignment of Mukonicine
  作者：Hans-Joachim Knölker、Christian Schuster、Marika Rönnefahrt、Konstanze Julich-Gruner、Anne Jäger、Arndt Schmidt

  DOI：10.1055/s-0035-1560359

  日期：——

  Using the palladium(II)-catalyzed oxidative cyclization of a diarylamine and the annulation of a dimethylpyran ring by Lewis acid promoted reaction with prenal as key steps, the total syntheses of the 6-oxygenated pyrano[3,2-a]carbazole alkaloids koenine and koenimbine, and of the 6,7-dioxygenated pyrano[3,2-a]carbazole alkaloids koenigine and koenigicine (koenimbidine, koenidine) were achieved. Moreover, these studies led to an improved synthetic route to the 2,6-dioxygenated carbazole alkaloid glycozolidol. Mukonicine, originally published as 6,8-dimethoxypyrano[3,2-a]carbazole, was found to be identical with koenigicine.
• Glycozolidol, an antibacterial carbazole alkaloid from Glycosmis pentaphylla
  作者：P. Bhattacharyya、P.K. Chakrabartty、B.K. Chowdhury

  DOI：10.1016/s0031-9422(00)84922-5

  日期：1985.1

  Abstract Glycozolidol, a new carbazole alkaloid, has been isolated from the roots of Glycosmis pentaphylla . Its structure has been established as 6-hydroxy-2-methoxy-3-methylcarbazole on the basis of physical and chemical evidence. The compound has been found to be active at some Gram-positive and Gram-negative bacteria.

  摘要 Glycozolidol 是一种新型咔唑生物碱，是从五叶糖衣的根中分离得到的。根据物理和化学证据确定其结构为6-羟基-2-甲氧基-3-甲基咔唑。已发现该化合物对某些革兰氏阳性和革兰氏阴性细菌具有活性。