bis(1-phenylethyl)-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-4,9-methanodipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate | 861823-28-1

• 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: bis(1-phenylethyl)-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-4,9-methanodipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate
• 英文别名: bis[(1S)-1-phenylethyl] 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: 861823-28-1
• 化学式: C₃₁H₃₂N₄O₄
• 分子量: 524.619
• InChiKey: MMBFUPWDHOBBOI-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  bis(1-phenylethyl)-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-4,9-methanodipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate 在 palladium on activated charcoal 氢气 、 三乙胺 、 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 15.0h， 生成 bis(benzotriazol-1-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-dicarboxylate
  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：

  (S)-1-phenylethyl 1-methyl-4-aminopyrrole-2-carboxylate hydrochloride 、 聚合甲醛 在 盐酸 作用下， 以 甲醇 、 水 、 二氯甲烷 为溶剂， 反应 20.0h， 以53%的产率得到bis(1-phenylethyl)-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-4,9-methanodipyrrolo-[3,2-b:3',2'-f][1,5]diazocine-2,7-dicarboxylate
  参考文献：
  名称：

  Preparation of the enantiomers of an N-methylpyrrole analogue of Tröger’s base

  摘要：

  The enantiomers of bis(1-phenylethyl)-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-dicarboxlate were obtained by crystallization-induced asymmetric transformation (CIAT). The CIAT was driven by the absolute configuration of the 1-phenylethyl groups present in their convalent structure. Thus, the first example of CIAT on Troger's base derivatives in the absence of a resolving agent is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.016

文献信息

• Preparation of the enantiomers of an N-methylpyrrole analogue of Tröger’s base
  作者：Martin Valík、Bohumil Dolenský、Eberhardt Herdtweck、Vladimír Král

  DOI：10.1016/j.tetasy.2005.04.016

  日期：2005.6

  The enantiomers of bis(1-phenylethyl)-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-dicarboxlate were obtained by crystallization-induced asymmetric transformation (CIAT). The CIAT was driven by the absolute configuration of the 1-phenylethyl groups present in their convalent structure. Thus, the first example of CIAT on Troger's base derivatives in the absence of a resolving agent is reported. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.