2-allyl-1-(2-phenylethynyl)-1,2,3,4-tetrahydroisoquinoline | 1356648-27-5

• 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: 2-allyl-1-(2-phenylethynyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(2-phenylethynyl)-2-prop-2-enyl-3,4-dihydro-1H-isoquinoline
• CAS: 1356648-27-5
• 化学式: C₂₀H₁₉N
• 分子量: 273.378
• InChiKey: BXFCULZQMHWGAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  N-allyl 1,2,3,4-tetrahydroisoquinoline 、 苯乙炔 在 monoamine oxidase type N D₅ 、 四氯金酸水合物 作用下， 以 aq. phosphate buffer 为溶剂， 反应 32.0h， 以42%的产率得到2-allyl-1-(2-phenylethynyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Concurrent Biocatalytic Oxidation and C–C Bond Formation via Gold Catalysis: One-Pot Alkynylation of N-Alkyl Tetrahydroisoquinolines

  摘要：

  A cross-dehydrogenative coupling process has been developed involving the enzymatic oxidation of tetrahydroisoquinolines (THIQ) together with gold-catalyzed C-C bond-formation. The transformation demonstrates the compatibility of gold-mediated chemocatalysis and mono amine oxidase biocatalysis which act co-operatively in one vessel. A range of N-alkyl THIQs were functionalized in this manner at C-(1) position in high yields.

  DOI：

  10.1021/acscatal.8b03169

文献信息

• Zinc(II)-Catalyzed Redox Cross-Dehydrogenative Coupling of Propargylic Amines and Terminal Alkynes for Synthesis of <i>N</i>-Tethered 1,6-Enynes
  作者：Tsuyuka Sugiishi、Hiroyuki Nakamura

  DOI：10.1021/ja211092q

  日期：2012.2.8

  The zinc(II)-catalyzed redox cross-dehydrogenative coupling (CDC) of propargylic amines and terminal alkynes proceeds to afford N-tethered 1,6-enynes. In the current CDC reaction, a C(sp)-C(sp(3)) bond is formed between the carbon adjacent to the nitrogen atom in the propargylic amine and the terminal carbon of the alkyne with reduction of the C-C triple bond of the propargylic amine, which acts as an internal oxidant.