N,N'-Bis<2,3-bis(acetyloxy)propyl>-5-<3-<(acetyloxy)methyl>-5-oxo-4-morpholinyl>-2,4,6-triiodo-1,3-benzenedicarboxamide | 166818-25-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: N,N'-Bis<2,3-bis(acetyloxy)propyl>-5-<3-<(acetyloxy)methyl>-5-oxo-4-morpholinyl>-2,4,6-triiodo-1,3-benzenedicarboxamide
• 英文别名: N,N'-Bis[2,3-bis(acetyloxy)propyl]-5-[3-((Acetyloxy)methyl)-5-oxo-4-morpholinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide；N,N'-bis[2,3-bis(acetyloxy)propyl]-5-[3-(Acetyloxy)methyl-5-oxo-4-morpholinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide；[4-[3,5-bis(2,3-diacetyloxypropylcarbamoyl)-2,4,6-triiodophenyl]-5-oxomorpholin-3-yl]methyl acetate
• CAS: 166818-25-3
• 化学式: C₂₉H₃₄I₃N₃O₁₄
• 分子量: 1029.31
• InChiKey: QWOPDKODLIYTEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  219
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  N,N'-Bis<2,3-bis(acetyloxy)propyl>-5-<3-<(acetyloxy)methyl>-5-oxo-4-morpholinyl>-2,4,6-triiodo-1,3-benzenedicarboxamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以80%的产率得到N,N'-Bis(2,3-dihydroxypropyl)-5-<3-(hydroxymethyl)-5-oxo-4-morpholinyl>-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：

  在 吡啶 、 N-碘代丁二酰亚胺 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 生成 N,N'-Bis<2,3-bis(acetyloxy)propyl>-5-<3-<(acetyloxy)methyl>-5-oxo-4-morpholinyl>-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

文献信息

• Nonionic radiographic contrast agents
  申请人：Bracco International B.V.

  公开号：US05591846A1

  公开（公告）日：1997-01-07

  New nonionic radiographic contrast agents having the formula ##STR1## wherein Y is a single bond, ##STR2## R.sub.1, R.sub.1 ' and R.sub.2 are the same or different and are hydrogen, alkyl or hydroxyalkyl. Hydroxyalkyl refers to such alkyl groups having 1 or more hydroxy groups. Preferred hydroxyalkyl groups include: ##STR3## R.sub.3 and R.sub.4 are the same or different and are hydrogen, methyl or --CH.sub.2 CH.sub.2 OH; R.sub.5 is hydrogen, alkyl, --CH.sub.2 CH.sub.2 OH, CH.sub.2 OH or OH and R.sub.6 is alkyl, --CH.sub.2 CH.sub.2 OH, CH.sub.2 OH, OH or hydrogen and may be the same or different than R.sub.5 and m is zero or one, with the proviso that no methylene or methine carbon atom of the heterocyclic ring is attached to both a nitrogen and an oxygen atom with the additional proviso that when Y is a single bond, m is not zero. These new contrast agents are water soluble and have desirable low osmolality and anticoagulant properties.

  新的非离子放射造影剂具有以下公式：##STR1## 其中Y是单键，##STR2## 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。羟基烷基是指具有1个或多个羟基的烷基基团。首选的羟基烷基包括：##STR3## 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，可以与R.sub.5相同或不同，m为零或一，但异环戊二烯环上的甲基或亚甲基碳原子不连接氮和氧原子。此外，当Y为单键时，m不为零。这些新的造影剂具有良好的水溶性、低渗透压和抗凝血性能。
• 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