3-benzyloxy-4-methoxy-2-(oxiranylmethyl)benzonitrile | 1370477-81-8

• 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: 3-benzyloxy-4-methoxy-2-(oxiranylmethyl)benzonitrile
• 英文别名: 4-Methoxy-2-(oxiran-2-ylmethyl)-3-phenylmethoxybenzonitrile；4-methoxy-2-(oxiran-2-ylmethyl)-3-phenylmethoxybenzonitrile
• CAS: 1370477-81-8
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: CXMJHLAPNMCUMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-4-methoxy-2-(oxiranylmethyl)benzonitrile 在 20 % Pd(OH)2/C 、 四丁基溴化铵 、 环己烯 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 17.0h， 生成 5-hydroxy-3-(cyanomethyl)-6-methoxy-3,4-dihydroisoquinolin-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
• 作为产物：
  描述：

  2-allyl-3-benzyloxy-4-methoxybenzonitrile 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以67%的产率得到3-benzyloxy-4-methoxy-2-(oxiranylmethyl)benzonitrile
  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.