5-n-butoxy-3-(cyanomethyl)-6-methoxy-3,4-dihydroiso-quinolin-1(2H)-one | 1370477-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5-n-butoxy-3-(cyanomethyl)-6-methoxy-3,4-dihydroiso-quinolin-1(2H)-one
• 英文别名: 2-(5-butoxy-6-methoxy-1-oxo-3,4-dihydro-2H-isoquinolin-3-yl)acetonitrile
• CAS: 1370477-85-2
• 化学式: C₁₆H₂₀N₂O₃
• 分子量: 288.346
• InChiKey: YEPBBGAVOFTTCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-allyl-3-n-butoxy-4-methoxybenzonitrile 在 四丁基溴化铵 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 5-n-butoxy-3-(cyanomethyl)-6-methoxy-3,4-dihydroiso-quinolin-1(2H)-one
  参考文献：
  名称：

  A novel and chemoselective synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones from o-oxiranylmethylbenzonitrile intermediates and TBAB/NaCN

  摘要：

  A novel synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones is described. o-Oxiranylmethylbenzonitriles, prepared from isovanillin via five synthetic steps, were treated with NaCN/tetra-n-butylammonium bromide (TBAB) to yield 3,4-dihydroisoquinolin-1(2H)-ones in good yields. This one pot reaction demonstrates the novel and chemoselective nature of ring-opening of epoxide by cyanide to generate an iminoisochroman ring via cyclization, again ring-opening by cyanide to generate a Michael acceptor and a donor, and ring re-cyclization through an intramolecular conjugate addition. The detailed mechanism is also rationally proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.023

文献信息

• A novel and chemoselective synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones from o-oxiranylmethylbenzonitrile intermediates and TBAB/NaCN
  作者：Po-Yuan Chen、Hsing-Ming Chen、Michael Y. Chiang、You-Feng Wang、Sie-Rong Li、Tzu-Pin Wang、Eng-Chi Wang

  DOI：10.1016/j.tet.2012.02.023

  日期：2012.4

  A novel synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones is described. o-Oxiranylmethylbenzonitriles, prepared from isovanillin via five synthetic steps, were treated with NaCN/tetra-n-butylammonium bromide (TBAB) to yield 3,4-dihydroisoquinolin-1(2H)-ones in good yields. This one pot reaction demonstrates the novel and chemoselective nature of ring-opening of epoxide by cyanide to generate an iminoisochroman ring via cyclization, again ring-opening by cyanide to generate a Michael acceptor and a donor, and ring re-cyclization through an intramolecular conjugate addition. The detailed mechanism is also rationally proposed. (C) 2012 Elsevier Ltd. All rights reserved.