Ethyl 2-[1-acetyl-2-(hydroxymethyl)indol-3-yl]acetate | 197069-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Ethyl 2-[1-acetyl-2-(hydroxymethyl)indol-3-yl]acetate
• CAS: 197069-35-5
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: NIURJBOAWVIQSI-UHFFFAOYSA-N

物化性质

• 沸点：
  432.7±35.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[1-acetyl-2-(hydroxymethyl)indol-3-yl]acetate 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以65%的产率得到9-Acetyl-1,4-dihydropyrano[3,4-b]indol-3-one
  参考文献：
  名称：

  A simple synthesis of N-acetyl-1,4-dihydropyrano[3,4-b]indol-3-one: Evidence for a stepwise ionic pathway in the generation of indole-2,3-quinodimethanes

  摘要：

  The fact that N-acetyl-1,4-dihydropyrano[3,4-b]indol-3-one, prepared from ethyl 2-methylindole-3-acetate in four steps, is inert towards thermal decarboxylation and that decarboxylation of other 1,4-dihydropyrano[3,4-b]indol-3-ones is accelerated by polar solvent and by electron-donating groups suggests that the decarboxylation is an ionic process. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01530-x
• 作为产物：
  描述：

  Ethyl 2-(1-acetyl-2-methylindol-3-yl)acetate 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 四氯化碳 为溶剂， 生成 Ethyl 2-[1-acetyl-2-(hydroxymethyl)indol-3-yl]acetate
  参考文献：
  名称：

  A simple synthesis of N-acetyl-1,4-dihydropyrano[3,4-b]indol-3-one: Evidence for a stepwise ionic pathway in the generation of indole-2,3-quinodimethanes

  摘要：

  The fact that N-acetyl-1,4-dihydropyrano[3,4-b]indol-3-one, prepared from ethyl 2-methylindole-3-acetate in four steps, is inert towards thermal decarboxylation and that decarboxylation of other 1,4-dihydropyrano[3,4-b]indol-3-ones is accelerated by polar solvent and by electron-donating groups suggests that the decarboxylation is an ionic process. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01530-x

文献信息

• A simple synthesis of N-acetyl-1,4-dihydropyrano[3,4-b]indol-3-one: Evidence for a stepwise ionic pathway in the generation of indole-2,3-quinodimethanes
  作者：Olga M. Jakiwczyk、Kent E. Nielsen、Helena Nandin de Carvalho、Gary I. Dmitrienko

  DOI：10.1016/s0040-4039(97)01530-x

  日期：1997.9

  The fact that N-acetyl-1,4-dihydropyrano[3,4-b]indol-3-one, prepared from ethyl 2-methylindole-3-acetate in four steps, is inert towards thermal decarboxylation and that decarboxylation of other 1,4-dihydropyrano[3,4-b]indol-3-ones is accelerated by polar solvent and by electron-donating groups suggests that the decarboxylation is an ionic process. (C) 1997 Elsevier Science Ltd.