methyl 3-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)propiolate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: methyl 3-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)propiolate
• 英文别名: methyl 3-[2-(4-methoxyphenyl)-3,4-dihydro-1H-isoquinolin-1-yl]prop-2-ynoate
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: JGFLZAVZZDGJJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-甲氧基苯基)-3,4-二氢-1H-异喹啉 、 丙炔酸甲酯 在 silica gel 、 铜 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 0.5h， 以72%的产率得到methyl 3-(2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)propiolate
  参考文献：
  名称：

  Solvent-Free Cross-Dehydrogenative Coupling Reactions under High Speed Ball-Milling Conditions Applied to the Synthesis of Functionalized Tetrahydroisoquinolines

  摘要：

  Solvent-free reaction using a high-speed ball milling technique has been first applied to cross-dehydrogenative coupling (CDC) reactions between tetrahydroisoquinolines and three types of pronucleophiles such as nitroalkanes, alkynes, and indoles. All coupling products were obtained in good yields at short reaction times (no more than 40 min). When alkynes and indoles were used as pronucleophile, the reactions can be catalyzed efficiently by recoverable copper balls without any additional metal catalyst.

  DOI：

  10.1021/jo2015533

文献信息

• Fast, solvent-free asymmetric alkynylation of prochiral sp3 C–H bonds in a ball mill for the preparation of optically active tetrahydroisoquinoline derivatives
  作者：Jingbo Yu、Zhenhua Li、Kanyan Jia、Zhijiang Jiang、Menglu Liu、Weike Su

  DOI：10.1016/j.tetlet.2013.02.007

  日期：2013.4

  Solvent-free asymmetric cross-dehydrogenative-coupling (CDC) reaction between the sp(3) C-H bond of prochiral CH2 and terminal alkynes was first studied under High-Speed Ball-Milling conditions. A series of optical active 1-alkynyl tetrahydroisoquinoline derivatives were achieved by using recoverable copper balls together with PyBox chiral ligand in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). All coupling products were obtained in good yields at short reaction time with enantiomeric excesses up to 79%. (C) 2013 Elsevier Ltd. All rights reserved.
• Solvent-Free Cross-Dehydrogenative Coupling Reactions under High Speed Ball-Milling Conditions Applied to the Synthesis of Functionalized Tetrahydroisoquinolines
  作者：Weike Su、Jingbo Yu、Zhenhua Li、Zhijiang Jiang

  DOI：10.1021/jo2015533

  日期：2011.11.4

  Solvent-free reaction using a high-speed ball milling technique has been first applied to cross-dehydrogenative coupling (CDC) reactions between tetrahydroisoquinolines and three types of pronucleophiles such as nitroalkanes, alkynes, and indoles. All coupling products were obtained in good yields at short reaction times (no more than 40 min). When alkynes and indoles were used as pronucleophile, the reactions can be catalyzed efficiently by recoverable copper balls without any additional metal catalyst.