2-(4-dibenzylaminobutyl)-isoindole-1,3-dione | 23608-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(4-dibenzylaminobutyl)-isoindole-1,3-dione
• 英文别名: N-(4-dibenzylaminobutyl)phthalimide；2-[4-(Dibenzylamino)butyl]isoindole-1,3-dione
• CAS: 23608-88-0
• 化学式: C₂₆H₂₆N₂O₂
• 分子量: 398.505
• InChiKey: IRLGZQPCYMMBQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-dibenzylaminobutyl)-isoindole-1,3-dione 在 一水合肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 35.5h， 生成 1-{3-[4-(dibenzylaminobutyl)amino]propionyl}-2-allylpiperidine
  参考文献：
  名称：

  Efficient Syntheses of Oncinotine and Neooncinotine

  摘要：

  We have synthesized two natural alkaloids, oncinotine (1) and neooncinotine (2), by means of efficient ring-closing metathesis (RCM) reactions. The required dienes for RCM were assembled from three basic components: 2-allylpiperidine (5), 9-decenoic acid (6), and diamines 7. We developed two different methods to achieve the linkage: the Michael addition of acrylamide and two amidations of succinic anhydride. The Grubbs catalyst was used to form the 17- and 18-membered lactams in 50% and 68% yields, respectively.

  DOI：

  10.1021/jo049526i
• 作为产物：
  描述：

  N-(4-溴丁基)邻苯二甲酰亚胺 、 二苄胺 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 72.0h， 以49%的产率得到2-(4-dibenzylaminobutyl)-isoindole-1,3-dione
  参考文献：
  名称：

  Reversal Agent and Linker Variants of Reversed Chloroquines: Activities against Plasmodium falciparum

  摘要：

  We have shown that "reversed chloroquine molecules" constructed from chloroquine-like and resistance "reversal-agent"-like cores can be powerful drugs against malaria (J. Med. Chem. 2006, 49, 5623-5625). Several reversed chloroquines are now presented that probe parameters governing the activities against chloroquine-resistant and chloroquine-sensitive malaria strains. The design is tolerant to linker and reversal agent changes, but it piperazinyl group adjacent to the quinoline, at least for the group Of Compounds studied here, may be detrimental.

  DOI：

  10.1021/jm900972u

文献信息

• Reversal Agent and Linker Variants of Reversed Chloroquines: Activities against <i>Plasmodium falciparum</i>
  作者：Simeon Andrews、Steven J. Burgess、Deborah Skaalrud、Jane Xu Kelly、David H. Peyton

  DOI：10.1021/jm900972u

  日期：2010.1.28

  We have shown that "reversed chloroquine molecules" constructed from chloroquine-like and resistance "reversal-agent"-like cores can be powerful drugs against malaria (J. Med. Chem. 2006, 49, 5623-5625). Several reversed chloroquines are now presented that probe parameters governing the activities against chloroquine-resistant and chloroquine-sensitive malaria strains. The design is tolerant to linker and reversal agent changes, but it piperazinyl group adjacent to the quinoline, at least for the group Of Compounds studied here, may be detrimental.
• Efficient Syntheses of Oncinotine and Neooncinotine
  作者：Duen-Ren Hou、Hsiu-Yi Cheng、Eng-Chi Wang

  DOI：10.1021/jo049526i

  日期：2004.9.1

  We have synthesized two natural alkaloids, oncinotine (1) and neooncinotine (2), by means of efficient ring-closing metathesis (RCM) reactions. The required dienes for RCM were assembled from three basic components: 2-allylpiperidine (5), 9-decenoic acid (6), and diamines 7. We developed two different methods to achieve the linkage: the Michael addition of acrylamide and two amidations of succinic anhydride. The Grubbs catalyst was used to form the 17- and 18-membered lactams in 50% and 68% yields, respectively.