N-(4-Cyano-3-methyl-1H-isochromen-1-yl)-acetamide | 161468-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(4-Cyano-3-methyl-1H-isochromen-1-yl)-acetamide
• 英文别名: N-(4-cyano-3-methyl-1H-isochromen-1-yl)acetamide
• CAS: 161468-36-6
• 化学式: C₁₃H₁₂N₂O₂
• 分子量: 228.25
• InChiKey: HBEPDOKGLOGGDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-Cyano-3-methyl-1H-isochromen-1-yl)-acetamide 在 sodium cyanoborohydride 作用下， 以 三氟乙酸 为溶剂， 反应 4.0h， 以51%的产率得到3-methyl-1H-isochromene-4-carbonitrile
  参考文献：
  名称：

  摘要：

  The reduction of 1-acetylamino-3-methylisochromene-4-carbonitrile and an N-butyl-1, 2-dihydroisoquinoline analogue with sodium borohydride and sodium cyanoborohydride in ethanol and carboxylic acid media are reported. Ready reduction at the 1-position occurred, followed by further reductive loss of the acetylamino group so formed. The ease of reduction of the 3,4-double bond was different for the O- and N-series but conditions were established for preparation of the fully reduced species. Sodium borohydride with cobalt chloride in methanol was effective at reducing the cyano function.

  DOI：

  10.1071/ch01015
• 作为产物：
  描述：

  1H-1-乙酰基亚氨基-3-甲基苯并[c]吡喃-4-甲腈 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以66%的产率得到N-(4-Cyano-3-methyl-1H-isochromen-1-yl)-acetamide
  参考文献：
  名称：

  α-氰基邻甲苯腈的乙酰化：异喹啉的再研究和便捷合成

  摘要：

  摘要 α-氰基邻甲苯腈二乙酰化的产物现已被指定为异香豆素衍生物。通过与氧、氮、碳和氢亲核试剂反应，这很容易转化为各种 1-取代-3-甲基异喹啉-4-腈。

  DOI：

  10.1080/00397919508011362

文献信息

• Acetylation of α-Cyano-<i>o</i>-tolunitrile: A Reinvestigation and Convenient Synthesis of Isoquinolines
  作者：L. W. Deady、N. H. Quazi

  DOI：10.1080/00397919508011362

  日期：1995.2

  Abstract The product from the diacetylation of α-cyano-o-tolunitrile has now been assigned as an isocoumarin derivative. This is readily transformed into various 1-substituted-3-methylisoquinoline-4-carbonitriles by reaction with oxygen, nitrogen, carbon and hydrogen nucleophiles.

  摘要 α-氰基邻甲苯腈二乙酰化的产物现已被指定为异香豆素衍生物。通过与氧、氮、碳和氢亲核试剂反应，这很容易转化为各种 1-取代-3-甲基异喹啉-4-腈。
• ——
  作者：Leslie W. Deady、Clare L. Smith

  DOI：10.1071/ch01015

  日期：——

  The reduction of 1-acetylamino-3-methylisochromene-4-carbonitrile and an N-butyl-1, 2-dihydroisoquinoline analogue with sodium borohydride and sodium cyanoborohydride in ethanol and carboxylic acid media are reported. Ready reduction at the 1-position occurred, followed by further reductive loss of the acetylamino group so formed. The ease of reduction of the 3,4-double bond was different for the O- and N-series but conditions were established for preparation of the fully reduced species. Sodium borohydride with cobalt chloride in methanol was effective at reducing the cyano function.