7-di-p-tosylamino-3-(tert-butyldiphenylsilanyloxy)methyl-4-ethylquinoline-2-carbaldehyde | 1013629-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-di-p-tosylamino-3-(tert-butyldiphenylsilanyloxy)methyl-4-ethylquinoline-2-carbaldehyde
• CAS: 1013629-43-0
• 化学式: C₄₃H₄₄N₂O₆S₂Si
• 分子量: 777.05
• InChiKey: FLMGNBXRAPZGBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.89
• 重原子数：
  54.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  110.71
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  7-di-p-tosylamino-3-(tert-butyldiphenylsilanyloxy)methyl-4-ethylquinoline-2-carbaldehyde 、 甲基色氨酸 以 xylene 为溶剂， 反应 5.0h， 以34%的产率得到1-[7-di-p-tosylamino-3-((tert-butyldiphenylsilanyloxy)methyl)-4-ethylquinolin-2-yl]-9H-β-carboline-3-carboxylic acid methyl ester
  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：

  7-di-p-tosylamino-3-(tert-butyldiphenylsilanyloxy)methyl-4-ethyl-2-methylquinoline 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 以2.670 g的产率得到7-di-p-tosylamino-3-(tert-butyldiphenylsilanyloxy)methyl-4-ethylquinoline-2-carbaldehyde
  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