1-[7-di-p-tosylamino-3-((tert-butyldiphenylsilanyloxy)methyl)-quinolin-2-yl]-9H-β-carboline-3-carboxylic acid methyl ester | 1013629-27-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-[7-di-p-tosylamino-3-((tert-butyldiphenylsilanyloxy)methyl)-quinolin-2-yl]-9H-β-carboline-3-carboxylic acid methyl ester
• 英文别名: methyl 1-[7-[bis-(4-methylphenyl)sulfonylamino]-3-[[tert-butyl(diphenyl)silyl]oxymethyl]quinolin-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1013629-27-0
• 化学式: C₅₃H₄₈N₄O₇S₂Si
• 分子量: 945.204
• InChiKey: ONYKANJBPGVQCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.0
• 重原子数：
  67
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  165
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-[7-di-p-tosylamino-3-((tert-butyldiphenylsilanyloxy)methyl)-quinolin-2-yl]-9H-β-carboline-3-carboxylic acid methyl ester 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以84%的产率得到1-[7-di-p-tosylamino-3-hydroxymethyl-quinolin-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-quinoline-2-carbaldehyde 、 甲基色氨酸 以 xylene 为溶剂， 反应 17.0h， 以46%的产率得到1-[7-di-p-tosylamino-3-((tert-butyldiphenylsilanyloxy)methyl)-quinolin-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

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.