N-[4,5-dimethoxy-2-(phenylethynyl)benzylidene]-tert-butylamine | 438564-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4,5-dimethoxy-2-(phenylethynyl)benzylidene]-tert-butylamine
• 英文别名: N-tert-butyl-1-[4,5-dimethoxy-2-(2-phenylethynyl)phenyl]methanimine
• CAS: 438564-93-3
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: SPCUMCCGNVUJFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[4,5-dimethoxy-2-(phenylethynyl)benzylidene]-tert-butylamine 、 (三氟甲基)三甲基硅烷 在 silver hexafluoroantimonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 以90%的产率得到2-tert-butyl-6,7-dimethoxy-3-phenyl-1-(trifluoromethyl)-1,2-dihydroisoquinoline
  参考文献：
  名称：

  Generation of 1-(trifluoromethyl)-1,2-dihydroisoquinolines via a silver(I)-catalyzed reaction of 2-alkynylaryl aldimine with trimethyl(trifluoromethyl)silane

  摘要：

  A silver(I)-catalyzed reaction of 2-alkynylaryl aldimine with trimethyl(trifluoromethyl)silane is reported. This reaction proceeds efficiently under extremely mild conditions to generate 1-(trifluoromethyl)-1,2-dihydroisoquinolines in good yields. A three-component reaction of 2-alkynylbenzaldehyde, amine, with trimethyl(trifluoromethyl)silane is presented as well. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.064
• 作为产物：
  描述：

  4,5-dimethoxy-2-(2-phenylethynyl)benzaldehyde 、 叔丁胺 反应 24.0h， 以1.32 g的产率得到N-[4,5-dimethoxy-2-(phenylethynyl)benzylidene]-tert-butylamine
  参考文献：
  名称：

  Synthesis of 4-(1-Alkenyl)isoquinolines by Palladium(II)-Catalyzed Cyclization/Olefination

  摘要：

  A variety of 4-(l-alkenyl)-3-arylisoquinolines have been prepared in moderate to excellent yields by the Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes. The introduction of an o-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Ketone-containing isoquinolines 36 and 49-51 have also been prepared by this process when unsaturated alcohols are employed as the alkenes.

  DOI：

  10.1021/jo0261303

文献信息

• Generation of 4-Cyanoisoquinolines and 4-Amidylisoquinolines<i>via</i>a Palladium-Catalyzed Cyanative Reaction of 2-Alkynylbenzaldimines with Isocyanides
  作者：Guanyinsheng Qiu、Xiaochen Qiu、Jie Wu

  DOI：10.1002/adsc.201300634

  日期：2013.11.11

  AbstractAn efficient route to 4‐cyanoquinolines via a palladium‐catalyzed cyanative reaction of 2‐alkynylbenzaldimines with isocyanides has been developed. The transformation proceeds through 6‐endo cyclization, isocyanide insertion, and cyanation. 4‐Amidylisoquinolines can be generated as well if water is involved in the reaction.magnified image
• Synthesis of 4-(1-Alkenyl)isoquinolines by Palladium(II)-Catalyzed Cyclization/Olefination
  作者：Qinhua Huang、Richard C. Larock

  DOI：10.1021/jo0261303

  日期：2003.2.1

  A variety of 4-(l-alkenyl)-3-arylisoquinolines have been prepared in moderate to excellent yields by the Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes. The introduction of an o-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Ketone-containing isoquinolines 36 and 49-51 have also been prepared by this process when unsaturated alcohols are employed as the alkenes.
• Generation of 1-(trifluoromethyl)-1,2-dihydroisoquinolines via a silver(I)-catalyzed reaction of 2-alkynylaryl aldimine with trimethyl(trifluoromethyl)silane
  作者：Xianbo Wang、Guanyinsheng Qiu、Ling Zhang、Jie Wu

  DOI：10.1016/j.tetlet.2013.12.064

  日期：2014.1

  A silver(I)-catalyzed reaction of 2-alkynylaryl aldimine with trimethyl(trifluoromethyl)silane is reported. This reaction proceeds efficiently under extremely mild conditions to generate 1-(trifluoromethyl)-1,2-dihydroisoquinolines in good yields. A three-component reaction of 2-alkynylbenzaldehyde, amine, with trimethyl(trifluoromethyl)silane is presented as well. (C) 2013 Elsevier Ltd. All rights reserved.