4-(3-aminoprop-1-yn-1-yl)benzonitrile

• 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: 4-(3-aminoprop-1-yn-1-yl)benzonitrile
• 英文别名: 4-(3-Aminoprop-1-ynyl)benzonitrile；4-(3-aminoprop-1-ynyl)benzonitrile
• 化学式: C₁₀H₈N₂
• 分子量: 156.187
• InChiKey: IKZGXKGIFQADOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-aminoprop-1-yn-1-yl)benzonitrile 、 5-phenyl-3-vinyl-1,2,4-triazine 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.5h， 以59%的产率得到4-(2-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-4-yl)benzonitrile
  参考文献：
  名称：

  Domino Aza-Michael-ih-Diels–Alder Reaction to Various 3-Vinyl-1,2,4-triazines: Access to Polysubstituted Tetrahydro-1,6-naphthyridines

  摘要：

  A straightforward domino aza-Michael-inverseelectron-demand-hetero-Diels Alder/retro-Diels-Alder reaction between primary and secondary propargylamine derivatives and 3-vinyl-1,2,4-triazines is developed highlighting not only the uniqueness of this dual-heterocyclic platform but also a novel and unprecedented path to polysubstituted tetrahydro-1,6-naphthyridine scaffolds.

  DOI：

  10.1021/acs.orglett.7b02132
• 作为产物：
  描述：

  tert-butyl (3-(4-cyanophenyl)prop-2-yn-1-yl)carbamate 在 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 以85%的产率得到4-(3-aminoprop-1-yn-1-yl)benzonitrile
  参考文献：
  名称：

  Domino Aza-Michael-ih-Diels–Alder Reaction to Various 3-Vinyl-1,2,4-triazines: Access to Polysubstituted Tetrahydro-1,6-naphthyridines

  摘要：

  A straightforward domino aza-Michael-inverseelectron-demand-hetero-Diels Alder/retro-Diels-Alder reaction between primary and secondary propargylamine derivatives and 3-vinyl-1,2,4-triazines is developed highlighting not only the uniqueness of this dual-heterocyclic platform but also a novel and unprecedented path to polysubstituted tetrahydro-1,6-naphthyridine scaffolds.

  DOI：

  10.1021/acs.orglett.7b02132

文献信息

• A Versatile and Efficient Palladium-<i>meta</i>-Terarylphosphine Catalyst for the Copper-Free Sonogashira Coupling of (Hetero-)Aryl Chlorides and Alkynes
  作者：Yong Yang、Xinying Chew、Charles W. Johannes、Edward G. Robins、Howard Jong、Yee Hwee Lim

  DOI：10.1002/ejoc.201402699

  日期：2014.11

  A novel meta-terarylphosphine ligand, Cy*Phine, was developed and found to be a highly active promoter of copper-free Sonogashira cross-coupling reactions when combined in situ with a palladium source. The evolutionary m-terarylphosphine ligand architecture was able to impose significant performance advantages over its biarylphosphine congeners. An expedient and versatile protocol was also devised

  一种新型间四芳基膦配体 Cy*Phine 被开发出来，当与钯源原位结合时，它是无铜 Sonogashira 交叉偶联反应的高活性促进剂。进化的间四芳基膦配体结构能够对其二芳基膦同系物施加显着的性能优势。还设计了一种方便和通用的协议，重点是适用于精细化工行业的底物，具有各种具有挑战性的、富含电子的芳基氯化物和末端炔烃。Pd-Cy*Phine 催化剂能够以高产率和有效的底物利用提供产物，这最大限度地减少了通常形成的副产物的产生，并且该反应可以耐受各种具有未保护官能团的底物。
• Domino Aza-Michael-<i>ih</i>-Diels–Alder Reaction to Various 3-Vinyl-1,2,4-triazines: Access to Polysubstituted Tetrahydro-1,6-naphthyridines
  作者：Jabrane Jouha、Floris Buttard、Magali Lorion、Clément Berthonneau、Mostafa Khouili、Marie-Aude Hiebel、Gérald Guillaumet、Jean-François Brière、Franck Suzenet

  DOI：10.1021/acs.orglett.7b02132

  日期：2017.9.15

  A straightforward domino aza-Michael-inverseelectron-demand-hetero-Diels Alder/retro-Diels-Alder reaction between primary and secondary propargylamine derivatives and 3-vinyl-1,2,4-triazines is developed highlighting not only the uniqueness of this dual-heterocyclic platform but also a novel and unprecedented path to polysubstituted tetrahydro-1,6-naphthyridine scaffolds.