2,4-diamino-5-methoxybenzaldehyde | 1013629-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4-diamino-5-methoxybenzaldehyde
• 英文别名: 2,4-Diamino-5-methoxybenzaldehyde
• CAS: 1013629-30-5
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: SOFYJNZZLISBPK-UHFFFAOYSA-N

物化性质

• 熔点：
  174.9-176.0 °C
• 沸点：
  387.2±42.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-diamino-5-methoxybenzaldehyde 、 乙酰乙酸甲酯 在 哌啶 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以1.691 g的产率得到7-氨基-6-甲氧基-2-甲基喹啉-3-羧酸甲酯
  参考文献：
  名称：

  Synthesis of new lavendamycin analogues

  摘要：

  Friedlander reaction between methyl acetoacetate and 2,4-diaminobenzaldehyde provided quinoline 11. Subsequent tosylation, reduction, silylation, and then oxidation led to aldehyde 15. The latter was subjected to a Pictet-Spengler reaction with tryptophan methyl ester that yielded product 16, and then desilylation gave the lavendamycin analogue 17. This compound was oxidized by Dess-Martin periodinane, and the cyclized derivative 18 was obtained via a hemiaminal intermediate. The same sequence from 2,4-diamino-5-methoxybenzaldehyde or from (2,4-diaminophenyl)propan-3-one led to compounds 30 and 31, or 40 and 41, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.016
• 作为产物：
  描述：

  3-甲氧基苯甲醛 在 硫酸 、 硝酸 、 盐酸 、 铁粉 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以1.14 g的产率得到2,4-diamino-5-methoxybenzaldehyde
  参考文献：
  名称：

  Synthesis of new lavendamycin analogues

  摘要：

  Friedlander reaction between methyl acetoacetate and 2,4-diaminobenzaldehyde provided quinoline 11. Subsequent tosylation, reduction, silylation, and then oxidation led to aldehyde 15. The latter was subjected to a Pictet-Spengler reaction with tryptophan methyl ester that yielded product 16, and then desilylation gave the lavendamycin analogue 17. This compound was oxidized by Dess-Martin periodinane, and the cyclized derivative 18 was obtained via a hemiaminal intermediate. The same sequence from 2,4-diamino-5-methoxybenzaldehyde or from (2,4-diaminophenyl)propan-3-one led to compounds 30 and 31, or 40 and 41, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.016

文献信息

• Synthesis of new lavendamycin analogues
  作者：Arnaud Nourry、Stéphanie Legoupy、François Huet

  DOI：10.1016/j.tet.2007.12.016

  日期：2008.2

  Friedlander reaction between methyl acetoacetate and 2,4-diaminobenzaldehyde provided quinoline 11. Subsequent tosylation, reduction, silylation, and then oxidation led to aldehyde 15. The latter was subjected to a Pictet-Spengler reaction with tryptophan methyl ester that yielded product 16, and then desilylation gave the lavendamycin analogue 17. This compound was oxidized by Dess-Martin periodinane, and the cyclized derivative 18 was obtained via a hemiaminal intermediate. The same sequence from 2,4-diamino-5-methoxybenzaldehyde or from (2,4-diaminophenyl)propan-3-one led to compounds 30 and 31, or 40 and 41, respectively. (C) 2008 Elsevier Ltd. All rights reserved.