dibenzyl 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate | 552318-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dibenzyl 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate
• 英文别名: dibenzyl-4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b:3',2'-f][1,5]-diazocin-2,7-dicarboxylate；Dibenzyl 5,12-dimethyl-1,5,8,12-tetrazatetracyclo[6.6.1.02,6.09,13]pentadeca-2(6),3,9(13),10-tetraene-4,11-dicarboxylate；dibenzyl 5,12-dimethyl-1,5,8,12-tetrazatetracyclo[6.6.1.02,6.09,13]pentadeca-2(6),3,9(13),10-tetraene-4,11-dicarboxylate
• CAS: 552318-07-7
• 化学式: C₂₉H₂₈N₄O₄
• 分子量: 496.566
• InChiKey: AJCNVMJFXLFZLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dibenzyl 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate 在 palladium on activated charcoal 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.3 kPa 条件下， 反应 20.0h， 生成 N,N'-bis(5-[3-dimethylaminopropyl]aminocarbonyl-1-methylpyrrol-3-yl)-4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxamide
  参考文献：
  名称：

  Tröger's base scaffold in racemic and chiral fashion as a spacer for bisdistamycin formation. Synthesis and DNA binding study

  摘要：

  Head-to-head' oligo-N-methylpyrrole peptide dimers linked by a methano[1,5]diazocin scaffold are presented in racemic as well as chiral fashion. Their DNA binding activities were assayed on calf thymus DNA, poly(dA-dT)(2), and poly(dC-dG)(2) by NMR and ECD spectroscopies, and fluorescence probe displacement assay. The presented dimers prefer AT sequences, but show higher affinity to poly(dC-dG)(2) than distamycin A. The (4R,9R) configuration of methanodiazocin bridge was found to be better suited for interaction with ct-DNA and poly(dA-dT)(2) than (4S,9S) configuration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.056
• 作为产物：
  描述：

  聚合甲醛 、 Benzyl 4-Amino-1-methylpyrrole-2-carboxylate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以63%的产率得到dibenzyl 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate
  参考文献：
  名称：

  含有N-甲基吡咯单元的新型杂环Tröger碱衍生物

  摘要：

  从4-氨基-N-甲基吡咯羧酸盐区域选择性地制备Tröger碱的新型类似物，收率很高。二苄基-4,9-甲醇-1,6-二甲基-4,5,9,10-四氢-1 H，6 H-二吡咯并-[3,2- b：3'，2'- f ]的催化加氢[1,5]二唑-2,7-二羧酸盐2b导致4,9-甲醇-1,6-二甲基-4,5,9,10-四氢-1 H，6 H-二吡咯并-[3,2- b：3'，2'- f ] [1,5]二唑-2,7-二羧酸3它通过酰胺方案用于制备Tröger天然抗生素的基础衍生物。通过多种光谱技术和化合物2b通过X射线晶体学表征了新型的Tröger杂环碱基。在N-甲基吡咯Tröger的基本骨架中引入胍作为末端基团，为制备水溶性衍生物提供了可能。

  DOI：

  10.1016/s0040-4039(03)00177-1

文献信息

• Novel heterocyclic Tröger's base derivatives containing N-methylpyrrole units
  作者：Martin Valı&#x;k、Bohumil Dolensky、Hana Petřı&#x;čková、Petr Vašek、Vladimı&#x;r Král

  DOI：10.1016/s0040-4039(03)00177-1

  日期：2003.3

  preparation of Tröger's base derivatives of natural antibiotics via an amide protocol. The novel heterocyclic Tröger's bases were characterized by a variety of spectroscopic techniques and compound 2b by X-ray crystallography. Incorporation of guanidine as the terminal group in the N-methylpyrrole Tröger's base skeleton opens the possibility for preparation of water soluble derivatives.

  从4-氨基-N-甲基吡咯羧酸盐区域选择性地制备Tröger碱的新型类似物，收率很高。二苄基-4,9-甲醇-1,6-二甲基-4,5,9,10-四氢-1 H，6 H-二吡咯并-[3,2- b：3'，2'- f ]的催化加氢[1,5]二唑-2,7-二羧酸盐2b导致4,9-甲醇-1,6-二甲基-4,5,9,10-四氢-1 H，6 H-二吡咯并-[3,2- b：3'，2'- f ] [1,5]二唑-2,7-二羧酸3它通过酰胺方案用于制备Tröger天然抗生素的基础衍生物。通过多种光谱技术和化合物2b通过X射线晶体学表征了新型的Tröger杂环碱基。在N-甲基吡咯Tröger的基本骨架中引入胍作为末端基团，为制备水溶性衍生物提供了可能。
• Selective formation of either Tröger’s base or spiro Tröger’s base derivatives from [2-aminoporphyrinato(2-)]nickel by choice of reaction conditions
  作者：Ameneh Tatar、Bohumil Dolenský、Hana Dvořáková、Vladimír Král

  DOI：10.1016/j.tetlet.2012.08.097

  日期：2012.11

  formaldehyde to form selectively either the symmetric Tröger’s base or the asymmetric spiro Tröger’s base bis(metalloporphyrin) derivative. The reaction is driven by the choice of acid catalyst, formaldehyde source, and particularly, solvent, to give a mixture of both derivatives in preparative yields of about 90%, or to give selectively one of the derivatives in a yield of about 60%.

  该文章报道了[2-氨基卟啉（2-）]镍与甲醛的酸催化反应的独特操作，该反应选择性地形成了对称的Tröger碱或不对称的螺环Tröger的碱双（金属卟啉）衍生物。通过选择酸催化剂，甲醛源，特别是溶剂来驱动反应，以制备产率约90％得到两种衍生物的混合物，或以产率约60％选择性地得到一种衍生物。
• Tröger's base scaffold in racemic and chiral fashion as a spacer for bisdistamycin formation. Synthesis and DNA binding study
  作者：Martin Valík、Jaroslav Malina、Lukáš Palivec、Jarmila Foltýnová、Marcela Tkadlecová、Marie Urbanová、Viktor Brabec、Vladimír Král

  DOI：10.1016/j.tet.2006.06.056

  日期：2006.9

  Head-to-head' oligo-N-methylpyrrole peptide dimers linked by a methano[1,5]diazocin scaffold are presented in racemic as well as chiral fashion. Their DNA binding activities were assayed on calf thymus DNA, poly(dA-dT)(2), and poly(dC-dG)(2) by NMR and ECD spectroscopies, and fluorescence probe displacement assay. The presented dimers prefer AT sequences, but show higher affinity to poly(dC-dG)(2) than distamycin A. The (4R,9R) configuration of methanodiazocin bridge was found to be better suited for interaction with ct-DNA and poly(dA-dT)(2) than (4S,9S) configuration. (c) 2006 Elsevier Ltd. All rights reserved.