N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-5-<2-<(acetyloxy)methyl>-5-oxo-1-pyrrolidinyl>-2,4,6-triiodo-1,3-benzenedicarboxamide | 166818-23-1

• 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>-5-<2-<(acetyloxy)methyl>-5-oxo-1-pyrrolidinyl>-2,4,6-triiodo-1,3-benzenedicarboxamide
• 英文别名: [1-[3,5-Bis(1,3-diacetyloxypropan-2-ylcarbamoyl)-2,4,6-triiodophenyl]-5-oxopyrrolidin-2-yl]methyl acetate
• CAS: 166818-23-1
• 化学式: C₂₉H₃₄I₃N₃O₁₃
• 分子量: 1013.31
• InChiKey: SCNIXORAYKJNSA-UHFFFAOYSA-N

物化性质

• 沸点：
  863.8±65.0 °C(Predicted)
• 密度：
  1.816±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  48
• 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：
  210
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-5-<2-<(acetyloxy)methyl>-5-oxo-1-pyrrolidinyl>-2,4,6-triiodo-1,3-benzenedicarboxamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以88%的产率得到N,N'-Bis<2-hydroxy-1-(hydroxymethyl)ethyl>-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：

  在 吡啶 、 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 生成 N,N'-Bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-5-<2-<(acetyloxy)methyl>-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