1-(pentyn-1-yl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline | 1418605-36-3

• 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: 1-(pentyn-1-yl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-pent-1-ynyl-2-phenyl-3,4-dihydro-1H-isoquinoline
• CAS: 1418605-36-3
• 化学式: C₂₀H₂₁N
• 分子量: 275.393
• InChiKey: UDEYNAGXRJYGSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  碘苯 在 叔丁基过氧化氢 、 copper(l) iodide 、 copper(l) chloride 作用下， 以 乙二醇 、 异丙醇 、 乙腈 为溶剂， 反应 72.0h， 生成 1-(pentyn-1-yl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Cu（I）在1,2,3,4-四氢异喹啉上催化一锅脱羧-炔基反应和一锅合成三唑基1,2,3,4-四氢异喹啉

  摘要：

  据报道，通过直接的C H-官能化将炔基引入生物学上有趣的1,2,3,4-四氢异喹啉的C-1位置的简便有效的方法。通过一锅两步脱羧反应，以氯化铜（I）为催化剂，炔酸为炔烃源，t-BuOOH为氧化剂，可以制得各种炔基化的N-取代的1,2,3,4-四氢异喹啉。中度到高产率的炔基化反应。此外，开发了导致1-三唑基-四氢异喹啉的三步脱羧-炔基-1,3-偶极环加成反应的一锅法方案，这是迄今未知的反应级联。

  DOI：

  10.1016/j.molcata.2016.07.013

文献信息

• Improved simplicity and practicability in copper-catalyzed alkynylation of tetrahydroisoquinoline
  作者：Birgit Gröll、Patricia Schaaf、Michael Schnürch

  DOI：10.1007/s00706-016-1877-5

  日期：2017.1

  AbstractAlkynylation reactions of N-protected tetrahydroisoquinolines have been performed using several different protocols of cross dehydrogenative coupling. Initially, a CuCl-catalyzed method was investigated, which worked well with three different N-protecting groups, namely phenyl, PMP, and benzyl and t-BuOOH as oxidant in acetonitrile as solvent. The peroxide could then be replaced by simple air

  AbstractN-保护的四氢异喹啉的炔基化反应已使用交叉脱氢偶联的几种不同方案进行。最初，研究了CuCl催化的方法，该方法在三种不同的N保护基（即苯基，PMP和苄基以及叔丁基OOH）作为氧化剂在乙腈中作为溶剂时效果很好。然后可以用简单的空气和乙腈代替水来生产过氧化物，从而实现总体上非常环保的方案。最后，还使用空气作为氧化剂，开发了从炔酸开始的脱羧烷基化方案。这避免了在引入短链炔烃取代基中使用气态炔烃。 图形概要
• 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.
• 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.
• Cu(I)-catalyzed one-pot decarboxylation-alkynylation reactions on 1,2,3,4-tetrahydroisoquinolines and one-pot synthesis of triazolyl-1,2,3,4-tetrahydroisoquinolines
  作者：Birgit Gröll、Patricia Schaaf、Marko D. Mihovilovic、Michael Schnürch

  DOI：10.1016/j.molcata.2016.07.013

  日期：2017.1

  A facile and efficient method to introduce alkyne groups to the C-1 position of biologically interesting 1,2,3,4-tetrahydroisoquinolines via direct CH-functionalization is reported. Various alkynylated N-substituted 1,2,3,4-tetrahydroisoquinolines could be obtained by using copper(I)-chloride as catalyst, alkynoic acids as alkyne source and t-BuOOH as oxidant, in a one-pot two-step decarboxylation-

  据报道，通过直接的C H-官能化将炔基引入生物学上有趣的1,2,3,4-四氢异喹啉的C-1位置的简便有效的方法。通过一锅两步脱羧反应，以氯化铜（I）为催化剂，炔酸为炔烃源，t-BuOOH为氧化剂，可以制得各种炔基化的N-取代的1,2,3,4-四氢异喹啉。中度到高产率的炔基化反应。此外，开发了导致1-三唑基-四氢异喹啉的三步脱羧-炔基-1,3-偶极环加成反应的一锅法方案，这是迄今未知的反应级联。