3-(isoquinolin-1-yl)-3-methyldihydrofuran-2(3H)-one

• 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: 3-(isoquinolin-1-yl)-3-methyldihydrofuran-2(3H)-one
• 英文别名: 3-Isoquinolin-1-yl-3-methyloxolan-2-one；3-isoquinolin-1-yl-3-methyloxolan-2-one
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: CWQIAEVOPXTWDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-氯异喹啉 、 α-甲基-γ-丁内酯 在 sodium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以69%的产率得到3-(isoquinolin-1-yl)-3-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  α-Heteroarylation of Esters, Lactones, Amides, and Lactams by Nucleophilic Aromatic Substitution

  摘要：

  A mild and efficient alpha-heteroarylation of simple esters and amides was developed via nucleophilic aromatic substitution. The choice of NaHMDS in toluene gave the best results. A tandem a-heteroarylation and hydroxylation protocol using air as the oxidant afforded tertiary alcohols in good yields.

  DOI：

  10.1021/ol060246u

文献信息

• Cyanide Anion as a Leaving Group in Nucleophilic Aromatic Substitution: Synthesis of Quaternary Centers at Azine Heterocycles
  作者：Alexander D. Thompson、Malcolm P. Huestis

  DOI：10.1021/jo302307y

  日期：2013.1.18

  Nucleophilic aromatic substitution of 2- or 4-cyanoazines with the anions derived from aliphatic α,α-disubstituted esters and nitriles leads to displacement of the cyanide function. Enabling cyanides to be used as highly active leaving groups in SNAr reactions provides additional flexibility in starting materials for synthesis. We show that, in many cases, the cyanide leaving group is displaced preferentially

  用衍生自脂族α，α-二取代的酯和腈的阴离子对2-或4-氰基嗪进行亲核芳族取代会导致氰化物官能团的置换。使氰化物能够在S N Ar反应中用作高活性离去基团，为合成原料提供了额外的灵活性。我们表明，在许多情况下，氰化物离去基团在卤素存在下优先被取代。所得的杂芳基碘化物，溴化物和氯化物随后可用作进一步化学多样化的处理方法。
• α-Heteroarylation of Esters, Lactones, Amides, and Lactams by Nucleophilic Aromatic Substitution
  作者：Hong C. Shen、Fa-Xiang Ding、Steven L. Colletti

  DOI：10.1021/ol060246u

  日期：2006.3.1

  A mild and efficient alpha-heteroarylation of simple esters and amides was developed via nucleophilic aromatic substitution. The choice of NaHMDS in toluene gave the best results. A tandem a-heteroarylation and hydroxylation protocol using air as the oxidant afforded tertiary alcohols in good yields.