N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-2,4,6-triiodo-5-<3-(iodomethyl)-5-oxo-4-morpholinyl>-1,3-benzenedicarboxamide | 166818-27-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-2,4,6-triiodo-5-<3-(iodomethyl)-5-oxo-4-morpholinyl>-1,3-benzenedicarboxamide
• 英文别名: N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-2,4,6-triiodo-5-[3-(iodomethyl)-5-oxo-4-morpholinyl]-1,3-benzene-dicarboxamide；N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-2,4,6-triiodo-5-[3-(iodomethyl)-5-oxo-4-morpholinyl]-1,3-benzenedicarboxamide；[3-acetyloxy-2-[[3-(1,3-diacetyloxypropan-2-ylcarbamoyl)-2,4,6-triiodo-5-[3-(iodomethyl)-5-oxomorpholin-4-yl]benzoyl]amino]propyl] acetate
• CAS: 166818-27-5
• 化学式: C₂₇H₃₁I₄N₃O₁₂
• 分子量: 1097.17
• InChiKey: QQKQBPVNZJQVGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  193
• 氢给体数：
  2
• 氢受体数：
  12

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-<3-(iodomethyl)-5-oxo-4-morpholinyl>-1,3-benzenedicarboxamide 在 silver(I) acetate 作用下， 以 溶剂黄146 为溶剂， 以82%的产率得到N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-5-<3-<(acetyloxy)methyl>-5-oxo-4-morpholinyl>-2,4,6-triiodo-1,3-benzenedicarboxamide
  参考文献：
  名称：

  Nonionic radiographic contrast agents

  摘要：

  新的非离子X线造影剂具有以下结构式：##STR1## 其中Y是单键，--CH.sub.2 CH.sub.2 --，--CH.sub.2 O--，--OCH.sub.2 --，##STR2## --CH.sub.2 --，--CH.sub.2 --CH.sub.2 --CH.sub.2 --，--O--或##STR3## R.sub.1，R.sub.1'和R.sub.2相同或不同，可以是氢，烷基或羟基烷基。羟基烷基指的是具有1个或更多羟基的烷基基团。首选的羟基烷基基团包括：##STR4## R.sub.3和R.sub.4相同或不同，可以是氢，甲基或--CH.sub.2 CH.sub.2 OH；R.sub.5是氢，烷基，--CH.sub.2 CH.sub.2 OH，CH.sub.2 OH或OH，R.sub.6是烷基，--CH.sub.2 CH.sub.2 OH，CH.sub.2 OH，OH或氢，可能与R.sub.5不同，m为零或一，但条件是杂环环的亚甲基或亚甲烷碳原子不同时连接到氮和氧原子，另外条件是当Y是单键时，m不为零。这些新的造影剂可溶于水，具有理想的低渗透压和抗凝血性能。

  公开号：

  US05614638A1
• 作为产物：
  描述：

  (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 吡啶 、 N-碘代丁二酰亚胺 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 24.5h， 生成 N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-2,4,6-triiodo-5-<3-(iodomethyl)-5-oxo-4-morpholinyl>-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

文献信息

• US5591846A
  申请人：——

  公开号：US5591846A

  公开（公告）日：1997-01-07
• US5614638A
  申请人：——

  公开号：US5614638A

  公开（公告）日：1997-03-25
• US5628980A
  申请人：——

  公开号：US5628980A

  公开（公告）日：1997-05-13