N,N'-bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-5-<4-(hydroxymethyl)-2-oxo-3-oxazolidinyl>-1,3-benzenedicarboxamide | 154921-15-0

• 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-<4-(hydroxymethyl)-2-oxo-3-oxazolidinyl>-1,3-benzenedicarboxamide
• 英文别名: N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-[4-(hydroxymethyl)-2-oxo-3-oxazolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide；[3-acetyloxy-2-[[3-(1,3-diacetyloxypropan-2-ylcarbamoyl)-5-[4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-2,4,6-triiodobenzoyl]amino]propyl] acetate
• CAS: 154921-15-0
• 化学式: C₂₆H₃₀I₃N₃O₁₃
• 分子量: 973.25
• InChiKey: RZTWCVAXFKTRNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  213
• 氢给体数：
  3
• 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-<4-(hydroxymethyl)-2-oxo-3-oxazolidinyl>-1,3-benzenedicarboxamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到N,N'-bis<2-hydroxy-1-(hydroxymethyl)ethyl>-2,4,6-triiodo-5-<4-(hydroxymethyl)-2-oxo-3-oxazolidinyl>-1,3-benzenedicarboxamide
  参考文献：
  名称：

  Heterocyclic Nonionic X-ray Contrast Agents. III. The Synthesis of 5-[4-(Hydroxymethyl)-2-oxo-3-oxazolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide Derivatives

  摘要：

  The syntheses of 2,4,6-triiodo-1,3-benzenedicarboxamide analogs, 12c, 12e, and 17c, of interest as X-ray diagnostic agents and in which the 5 position is linked to the N atom of a 4-(hydroxymethyl)-oxazolidin-2-one moiety, are described. The heterocycle was built from suitably protected 5-amino-2, 4,6-triiodo-1,3-benzenedicarboxylic acid derivatives by a three-step procedure consisting of (1) phosgene treatment to obtain the corresponding isocyanates, (2) phenylmercuric chloride-catalyzed addition of glycidol (10) resulting in glycidyl carbamates, and (3) pyridine-catalyzed intramolecular N-alkylation, followed by deprotection, to obtain the oxazolidin-2-ones. The intramolecular N-alkylation reaction was highly regioselective and was not appreciably accompanied by O-alkylation products under the experimental conditions employed. The two carboxamide nitrogen atoms in the intermediates and end products carry either 2,3-dihydroxypropyl or 1,3-dihydroxypropyl residues. These highly congested benzenoid compounds exhibited interesting NMR spectral features due to atropisomerism arising from hindrance to free rotation about the three single bonds that link the aromatic moiety to the N-containing functionalities.

  DOI：

  10.1021/jo00085a023
• 作为产物：
  描述：

  5-氨基-2,4,6-三碘异酞酰氯 在 吡啶 、 乙酸苯汞 吡啶 作用下， 以 1,4-二氧六环 、 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 43.0h， 生成 N,N'-bis<2-(acetyloxy)-1-<(acetyloxy)methyl>ethyl>-5-<4-(hydroxymethyl)-2-oxo-3-oxazolidinyl>-1,3-benzenedicarboxamide
  参考文献：
  名称：

  Heterocyclic Nonionic X-ray Contrast Agents. III. The Synthesis of 5-[4-(Hydroxymethyl)-2-oxo-3-oxazolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide Derivatives

  摘要：

  The syntheses of 2,4,6-triiodo-1,3-benzenedicarboxamide analogs, 12c, 12e, and 17c, of interest as X-ray diagnostic agents and in which the 5 position is linked to the N atom of a 4-(hydroxymethyl)-oxazolidin-2-one moiety, are described. The heterocycle was built from suitably protected 5-amino-2, 4,6-triiodo-1,3-benzenedicarboxylic acid derivatives by a three-step procedure consisting of (1) phosgene treatment to obtain the corresponding isocyanates, (2) phenylmercuric chloride-catalyzed addition of glycidol (10) resulting in glycidyl carbamates, and (3) pyridine-catalyzed intramolecular N-alkylation, followed by deprotection, to obtain the oxazolidin-2-ones. The intramolecular N-alkylation reaction was highly regioselective and was not appreciably accompanied by O-alkylation products under the experimental conditions employed. The two carboxamide nitrogen atoms in the intermediates and end products carry either 2,3-dihydroxypropyl or 1,3-dihydroxypropyl residues. These highly congested benzenoid compounds exhibited interesting NMR spectral features due to atropisomerism arising from hindrance to free rotation about the three single bonds that link the aromatic moiety to the N-containing functionalities.

  DOI：

  10.1021/jo00085a023

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。
• Pillai K. M. R., Diamantidis G., Duncan L., Ranganathan R. S., J. Org. Chem, 59 (1994) N 6, S 1344-1350
  作者：Pillai K. M. R., Diamantidis G., Duncan L., Ranganathan R. S.

  DOI：——

  日期：——
• 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