3-ethoxy-4-methoxy-2-oxiranylmethylbenzonitrile | 1370477-77-2

• 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-ethoxy-4-methoxy-2-oxiranylmethylbenzonitrile
• 英文别名: 3-Ethoxy-4-methoxy-2-(oxiran-2-ylmethyl)benzonitrile
• CAS: 1370477-77-2
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: KHVJTQZPDANXBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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-ethoxy-4-methoxy-2-oxiranylmethylbenzonitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以87%的产率得到5-ethoxy-6-methoxy-3-methyl-3,4-dihydroisocoumarin
  参考文献：
  名称：

  邻（环氧乙烷基甲基）苄腈与硼氢化钠或格氏试剂/CuI 的反应：取代 3-烷基-3,4-二氢异香豆素的新合成

  摘要：

  描述了一种合成取代的 3-烷基-3,4-二氢异香豆素的新方法。邻（环氧乙烷基甲基）苄腈，由异香草醛分五步制备，当与亲核试剂如硼氢化钠或苯基氯化镁/CuI 反应时，经过分子内环化，在一锅中以良好的收率得到目标化合物。

  DOI：

  10.3998/ark.5550190.0014.310
• 作为产物：
  描述：

  2-allyl-3-ethoxy-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83%的产率得到3-ethoxy-4-methoxy-2-oxiranylmethylbenzonitrile
  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.
• Reaction of o-(oxiranylmethyl)benzonitriles with sodium borohydride or Grignard reagent/CuI: a new synthesis of substituted 3-alkyl-3,4-dihydroisocoumarins
  作者：Po-Yuan Chen、You-Feng Wang、Liang-Yeu Chen、Guan-Lun Wang、Eng-Chi Wang

  DOI：10.3998/ark.5550190.0014.310

  日期：——

  A new method for the synthesis of substituted 3-alkyl-3,4-dihydroisocoumarins is described. o-(Oxiranylmethyl)benzonitriles, prepared from isovanillin in five steps, when reacted with nucleophiles such as sodium borohydride or phenylmagnesium chloride/CuI, undergo an intramolecular cyclization to yield the target compounds in good yields, in one pot.

  描述了一种合成取代的 3-烷基-3,4-二氢异香豆素的新方法。邻（环氧乙烷基甲基）苄腈，由异香草醛分五步制备，当与亲核试剂如硼氢化钠或苯基氯化镁/CuI 反应时，经过分子内环化，在一锅中以良好的收率得到目标化合物。