N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-2,4,6-triiodo-5-<(1-oxo-4-pentenoyl)amino>-1,3-benzenedicarboxamide | 148051-09-6

• 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: N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-2,4,6-triiodo-5-<(1-oxo-4-pentenoyl)amino>-1,3-benzenedicarboxamide
• 英文别名: N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)-methyl]ethyl]-2,4,6-triiodo-5-[(1-oxo-4-pentenyl)amino]-1,3-benzenedicarboxamide；N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)-methyl]ethyl]-2,4,6-triiodo-5-[(1-oxo-4-pentenyl) amino]-1,3-benzenedicarboxamide；[3-acetyloxy-2-[[3-(1,3-diacetyloxypropan-2-ylcarbamoyl)-2,4,6-triiodo-5-(pent-4-enoylamino)benzoyl]amino]propyl] acetate
• CAS: 148051-09-6
• 化学式: C₂₇H₃₂I₃N₃O₁₁
• 分子量: 955.278
• InChiKey: ZNKCDAYCZACSOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  44
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  193
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-2,4,6-triiodo-5-<(1-oxo-4-pentenoyl)amino>-1,3-benzenedicarboxamide 在 N-碘代丁二酰亚胺 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-5-<<5-<(acetyloxy)methyl>dihydro-2(3H)-furanylidene>amino>-2,4,6-triiodo-1,3-benzenedicarboxamide
  参考文献：
  名称：

  Heterocyclic Nonionic X-ray Contrast Agents. 4. The Synthesis of Dihydro-2(3H)-furanylidenamino, 5-oxo-1-pyrrolidinyl, and 5-oxo-4-morpholinyl Derivatives by an Intramolecular Iodocyclization Approach

  摘要：

  Intramolecular iodocyclization of omega-alkenylanilides 6 and [omega-(alkenyloxy)alkyl]anilides 7 resulted in the formation of dihydro-2(3H)-furanylidenamines 8 and 1,4-dioxan-2-ylideneamines 9, respectively, by an amide-oxygen participative nucleophilic attack on the expected iodonium intermediate. The latter heterocyclic ring system is new. If a strong base is present, the mode of ring closure was mainly diverted to an amide-nitrogen participative nucleophilic attack, leading to (iodomethyl)-pyrrolidinones 10 and (iodomethyl)morpholinones 11, from 6 and 7, respectively. Unique interconvertible syn-anti isomerism in the imino-ether 8a was demonstrated by variable temperature NMR studies. The major component in this mixture was the 8a anti-isomer. Acetolysis of the iodocyclized products, followed by deacetylation, provided the heterocyclically substituted polyhydroxytriiodoisophthalamides 16-18. Hydrolytic studies on the imidate 16d revealed an interesting pH dependence. As expected the amine 3d and the amide 22 resulted in pH values of 2 and 6. At pH 12, however, the Chapman rearrangement product 17d was the major product. The compounds obtained in this investigation are of interest as X-ray contrast agents.

  DOI：

  10.1021/jo00119a020
• 作为产物：
  描述：

  4-戊烯酰氯 、 (5-氨基-2,4,6-三碘-1,3-亚苯基)二(羰基亚氨基-2,1,3-丙烷三基)四乙酸酯 在 N,N-二甲基乙酰胺 、 乙酸乙酯 、 碳酸氢钠 、 水 、 Brine 、 crude product 、 丙酮 、 正己烷 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以afforded the title A compound (42.5 g), m.p. 162°-64°的产率得到N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-2,4,6-triiodo-5-<(1-oxo-4-pentenoyl)amino>-1,3-benzenedicarboxamide
  参考文献：
  名称：

  Methods and compositions for using non-ionic contrast agents to reduce

  摘要：

  根据本发明，揭示了一种使用非离子造影剂的新方法和组合物，以减少诊断过程中凝血形成的风险。还揭示了用于该方法的新组合物。本方法包括使用具有杂环基团的三碘苯类对比剂或具有一个或多个杂环基团的二聚三碘苯类对比剂。

  公开号：

  US05869024A1

文献信息

• Methods and compositions for using non-ionic contrast agents to reduce
  申请人：Bracco International B.V.

  公开号：US05527926A1

  公开（公告）日：1996-06-18

  In accordance with the present invention a novel method and composition for using nonionic contrast media to reduce the risk of clot formation in a diagnostic procedure is disclosed. Novel compositions for such method are also disclosed. The present method comprises employing a triiodinated phenyl contrast agent having a heterocyclic group or a dimeric triiodinated phenyl contrast agent having one or more heterocyclic groups.

  根据本发明，公开了一种新的方法和组合物，用于使用非离子造影剂来减少诊断过程中凝血风险。还公开了用于此类方法的新型组合物。本方法包括使用具有杂环基团的三碘苯造影剂或具有一个或多个杂环基团的二聚三碘苯造影剂。
• Methods and compositions for using non-ionic contrast agents to reduce the risk of clot formation in diagnostic procedures
  申请人：BRACCO INTERNATIONAL B.V.

  公开号：EP0516050A2

  公开（公告）日：1992-12-02

  In accordance with the present invention a novel method and composition for using nonionic contrast media to reduce the risk of clot formation in a diagnostic procedure is disclosed. Novel compositions for such method are also disclosed. The present method comprises employing a triiodinated phenyl contrast agent having a heterocyclic group or a dimeric triiodinated phenyl contrast agent having one or more heterocyclic groups.

  根据本发明，公开了一种使用非离子造影剂降低诊断过程中血栓形成风险的新型方法和组合物。本发明还公开了用于这种方法的新型组合物。本方法包括使用具有杂环基团的三碘苯基造影剂或具有一个或多个杂环基团的二聚三碘苯基造影剂。
• US5527926A
  申请人：——

  公开号：US5527926A

  公开（公告）日：1996-06-18
• Heterocyclic Nonionic X-ray Contrast Agents. 4. The Synthesis of Dihydro-2(3H)-furanylidenamino, 5-oxo-1-pyrrolidinyl, and 5-oxo-4-morpholinyl Derivatives by an Intramolecular Iodocyclization Approach
  作者：T. Arunachalam、H. Fan、K. M. R. Pillai、R. S. Ranganathan

  DOI：10.1021/jo00119a020

  日期：1995.7

  Intramolecular iodocyclization of omega-alkenylanilides 6 and [omega-(alkenyloxy)alkyl]anilides 7 resulted in the formation of dihydro-2(3H)-furanylidenamines 8 and 1,4-dioxan-2-ylideneamines 9, respectively, by an amide-oxygen participative nucleophilic attack on the expected iodonium intermediate. The latter heterocyclic ring system is new. If a strong base is present, the mode of ring closure was mainly diverted to an amide-nitrogen participative nucleophilic attack, leading to (iodomethyl)-pyrrolidinones 10 and (iodomethyl)morpholinones 11, from 6 and 7, respectively. Unique interconvertible syn-anti isomerism in the imino-ether 8a was demonstrated by variable temperature NMR studies. The major component in this mixture was the 8a anti-isomer. Acetolysis of the iodocyclized products, followed by deacetylation, provided the heterocyclically substituted polyhydroxytriiodoisophthalamides 16-18. Hydrolytic studies on the imidate 16d revealed an interesting pH dependence. As expected the amine 3d and the amide 22 resulted in pH values of 2 and 6. At pH 12, however, the Chapman rearrangement product 17d was the major product. The compounds obtained in this investigation are of interest as X-ray contrast agents.