1-苄基-5-甲氧基-N,N-二甲基-1H-吲哚-3-乙酰胺 | 419569-94-1

• 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
• 中文名称: 1-苄基-5-甲氧基-N,N-二甲基-1H-吲哚-3-乙酰胺
• 英文名称: 1-benzyl-5-methoxy-N,N-dimethyl-1H-indole-3-acetamide
• 英文别名: 2-(1-benzyl-5-methoxyindol-3-yl)-N,N-dimethylacetamide
• CAS: 419569-94-1
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: KYZLMKWKFPJCPD-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C
• 沸点：
  533.9±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-苄基-5-甲氧基-N,N-二甲基-1H-吲哚-3-乙酰胺 在 lithium aluminium tetrahydride 、 sodium 、 三溴化硼 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 氨 为溶剂， 反应 49.5h， 生成 蟾毒色胺
  参考文献：
  名称：

  Aromatization of 1,6,7,7a-Tetrahydro-2H-indol-2-ones by a Novel Process. Preparation of Key-Intermediate Methyl 1-Benzyl-5-methoxy-1H-indole-3-acetate and the Syntheses of Serotonin, Melatonin, and Bufotenin

  摘要：

  Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl3, leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.

  DOI：

  10.1021/jo0110597
• 作为产物：
  描述：

  二甲胺 、 1-苄基-5-甲氧基-1H-吲哚-3-乙酸甲酯 在 氰化钠 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以90%的产率得到1-苄基-5-甲氧基-N,N-二甲基-1H-吲哚-3-乙酰胺
  参考文献：
  名称：

  Aromatization of 1,6,7,7a-Tetrahydro-2H-indol-2-ones by a Novel Process. Preparation of Key-Intermediate Methyl 1-Benzyl-5-methoxy-1H-indole-3-acetate and the Syntheses of Serotonin, Melatonin, and Bufotenin

  摘要：

  Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl3, leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.

  DOI：

  10.1021/jo0110597

文献信息

• Aromatization of 1,6,7,7a-Tetrahydro-2<i>H</i>-indol-2-ones by a Novel Process. Preparation of Key-Intermediate Methyl 1-Benzyl-5-methoxy-1<i>H</i>-indole-3-acetate and the Syntheses of Serotonin, Melatonin, and Bufotenin
  作者：Gilbert Revial、Ivan Jabin、Sethy Lim、Michel Pfau

  DOI：10.1021/jo0110597

  日期：2002.4.1

  Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl3, leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.