9-acetyl-2-methoxy-6-methylcarbazole

• 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: 9-acetyl-2-methoxy-6-methylcarbazole
• 英文别名: 1-(2-methoxy-6-methyl-9H-carbazol-9-yl)ethanone；9-Acetyl-2-methoxy-6-methylcarbazole；1-(2-methoxy-6-methylcarbazol-9-yl)ethanone
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: UZCWYLOQSRTFCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2'-溴-4'-甲基乙酰苯胺 在 氧气 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate 、 potassium phosphate 、 copper diacetate 、 3 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 9-acetyl-2-methoxy-6-methylcarbazole
  参考文献：
  名称：

  Combined C−H Functionalization/C−N Bond Formation Route to Carbazoles

  摘要：

  A new method in which a series of substituted carbazoles is efficiently produced by the combination of an amide and an arene is described. The key feature of this method is the palladium-catalyzed tandem directed C-H functionalization and amide arylation. The method tolerates substitution on either ring of the biaryl amide substrates, and the products can be assembled in a simple two-step protocol from readily available reagents. The Pd(0) species generated are reoxidized to Pd(II) in the presence of Cu(OAc)2 and an atmosphere of oxygen.

  DOI：

  10.1021/ja055353i

文献信息

• Transition-metal-free and organic solvent-free conversion of <i>N</i>-substituted 2-aminobiaryls into corresponding carbazoles <i>via</i> intramolecular oxidative radical cyclization induced by peroxodisulfate
  作者：Palani Natarajan、Priya Priya、Deachen Chuskit

  DOI：10.1039/c7gc03130k

  日期：——

  benign approach for the synthesis of N-substituted carbazoles from analogous 2-aminobiaryls using peroxodisulfate in water is reported. The reactions proceeded through an intramolecular oxidative radical cyclization of N-substituted 2-aminobiaryls with in situ reoxidation of the resulting radical species. When compared to known methods for the synthesis of N-substituted carbazoles from 2-amidobiaryls, this

  报道了在水中使用过二硫酸盐从类似的2-氨基联芳基合成N-取代的咔唑的原子经济和环境友好的方法。该反应通过N-取代的2-氨基联芳基的分子内氧化自由基环化进行，并且原位再氧化所得的自由基物质。当与从2-酰胺基二芳基合成N-取代的咔唑的已知方法相比时，该方案是实用，有效的并且不需要过渡金属催化剂或有毒的有机溶剂。
• Palladium-Catalyzed Method for the Synthesis of Carbazoles via Tandem C−H Functionalization and C−N Bond Formation
  作者：W. C. Peter Tsang、Rachel H. Munday、Gordon Brasche、Nan Zheng、Stephen L. Buchwald

  DOI：10.1021/jo801273q

  日期：2008.10.3

  The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C-H bond and the formation of a new arene C-N bond. The substitution pattern of the carbazole product can be controlled by the design of the biaryl amide substrate, and the method is compatible with a variety of functional groups

  据报道，开发了一种组装不对称咔唑的新方法。该策略涉及芳烃CH键的选择性分子内功能化和新芳烃CN键的形成。咔唑产物的取代模式可以通过联芳酰胺底物的设计来控制，并且该方法与多种官能团兼容。通过从市售材料中简明合成三种天然产物，证明了新方案的实用性。
• Combined C−H Functionalization/C−N Bond Formation Route to Carbazoles
  作者：W. C. Peter Tsang、Nan Zheng、Stephen L. Buchwald

  DOI：10.1021/ja055353i

  日期：2005.10.1

  A new method in which a series of substituted carbazoles is efficiently produced by the combination of an amide and an arene is described. The key feature of this method is the palladium-catalyzed tandem directed C-H functionalization and amide arylation. The method tolerates substitution on either ring of the biaryl amide substrates, and the products can be assembled in a simple two-step protocol from readily available reagents. The Pd(0) species generated are reoxidized to Pd(II) in the presence of Cu(OAc)2 and an atmosphere of oxygen.