4-((9H-carbazol-9-yl)(phenyl)methyl)-2,6-di-methylphenol

• 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: 4-((9H-carbazol-9-yl)(phenyl)methyl)-2,6-di-methylphenol
• 英文别名: 4-[Carbazol-9-yl(phenyl)methyl]-2,6-dimethylphenol
• 化学式: C₂₇H₂₃NO
• 分子量: 377.486
• InChiKey: HBSUTUPWVHLWTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  、 咔唑 在 zinc trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 以80%的产率得到4-((9H-carbazol-9-yl)(phenyl)methyl)-2,6-di-methylphenol
  参考文献：
  名称：

  1,6-Aza-Michael addition of para-quinone methides with N-heterocycles catalyzed by Zn(OTf)2: A regioselective approach to N-diarylmethyl-substituted heterocycles

  摘要：

  An efficient Zn(OTf)(2)-catalyzed regioselective C-N bond making reaction between a bunch of aryl/heteroaryl-substituted para-quinone methides as ideal 1,6-acceptors and various aromatic/non-aromatic aza-heterocycles bearing N-H moiety namely carbazoles, pyrazoles, indazole, benzotriazole and saccharin is reported. This 1,6-aza-Michael technique delivers predominantly NI-diarylmethyl-substituted heterocyclic scaffolds bearing a valuable phenolic moiety in good to high yields with an excellent regioselectivity. Furthermore, this LUMO lowering catalytic system allows different kinds of useful functionalities and excels with broad substrates under mild conditions. Importantly, our control experiments suggested that N2-adducts of indazole, benzotriazole and 3-methyl pyrazole as minor isomers were progressively converted into N1-adducts during the reaction via a retro-aza-Michael reaction triggered by Zn(OTf)(2), offering excellent regioselectivities of the products. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131338

文献信息

• 1,6-Aza-Michael addition of para-quinone methides with N-heterocycles catalyzed by Zn(OTf)2: A regioselective approach to N-diarylmethyl-substituted heterocycles
  作者：Soumitra Guin、Hemonta K. Saha、Ashvani K. Patel、Santosh K. Gudimella、Subhankar Biswas、Sampak Samanta

  DOI：10.1016/j.tet.2020.131338

  日期：2020.7

  An efficient Zn(OTf)(2)-catalyzed regioselective C-N bond making reaction between a bunch of aryl/heteroaryl-substituted para-quinone methides as ideal 1,6-acceptors and various aromatic/non-aromatic aza-heterocycles bearing N-H moiety namely carbazoles, pyrazoles, indazole, benzotriazole and saccharin is reported. This 1,6-aza-Michael technique delivers predominantly NI-diarylmethyl-substituted heterocyclic scaffolds bearing a valuable phenolic moiety in good to high yields with an excellent regioselectivity. Furthermore, this LUMO lowering catalytic system allows different kinds of useful functionalities and excels with broad substrates under mild conditions. Importantly, our control experiments suggested that N2-adducts of indazole, benzotriazole and 3-methyl pyrazole as minor isomers were progressively converted into N1-adducts during the reaction via a retro-aza-Michael reaction triggered by Zn(OTf)(2), offering excellent regioselectivities of the products. (C) 2020 Elsevier Ltd. All rights reserved.