N,N'-Bis<2,3-bis(acetyloxy)propyl>-2,4,6-triiodo-5-<(1-oxo-4-pentenoyl)amino>-1,3-benzenedicarboxamide | 148051-05-2

• 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<2,3-bis(acetyloxy)propyl>-2,4,6-triiodo-5-<(1-oxo-4-pentenoyl)amino>-1,3-benzenedicarboxamide
• 英文别名: [2-Acetyloxy-3-[[3-(2,3-diacetyloxypropylcarbamoyl)-2,4,6-triiodo-5-(pent-4-enoylamino)benzoyl]amino]propyl] acetate
• CAS: 148051-05-2
• 化学式: C₂₇H₃₂I₃N₃O₁₁
• 分子量: 955.278
• InChiKey: RMJIRJZIZPNKLP-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<2,3-bis(acetyloxy)propyl>-2,4,6-triiodo-5-<(1-oxo-4-pentenoyl)amino>-1,3-benzenedicarboxamide 在 吡啶 、 N-碘代丁二酰亚胺 、 sodium methylate 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 5-<2-(Hydroxymethyl)-5-oxo-1-pyrrolidinyl>--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 、 tetra-O-acetyl-1-amino-3,5-bis-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodobenzene 以 N,N-二甲基乙酰胺 为溶剂， 以89%的产率得到N,N'-Bis<2,3-bis(acetyloxy)propyl>-2,4,6-triiodo-5-<(1-oxo-4-pentenoyl)amino>-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