dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate | 154921-11-6

• 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: dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate
• 英文别名: 1,3-dimethyl 5-amino-2,4,6-triiodoisophthalate；5-amino-2,4,6-triiodoisophthalic acid dimethyl ester；5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid, dimethyl ester；dimethyl 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylate
• CAS: 154921-11-6
• 化学式: C₁₀H₈I₃NO₄
• 分子量: 586.891
• InChiKey: ZHGAAXSHLQHKEP-UHFFFAOYSA-N

物化性质

• 沸点：
  500.4±50.0 °C(Predicted)
• 密度：
  2.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate 在 N-碘代丁二酰亚胺 作用下， 以 氯仿 、 N,N-二甲基乙酰胺 为溶剂， 反应 35.5h， 生成 2,4,6-Triiodo-5-<<6-(iodomethyl)-1,4-dioxan-2-ylidene>amino>-1,3-benzenedicarboxylic acid dimethyl ester
  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：

  5-氨基间苯二甲酸 在 potassium dichloroiodate 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 20.0h， 生成 dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate
  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

• Heterocyclic nonionic X-ray contrast agents V: A facile conversion of 2-tetrahydrofuroamides into α-hydroxy-δ-valerolactams and a general synthesis of lactams conjugated to 2,4,6-triiodoisophthalamides
  作者：E.R. Marinelli、T. Arunachalam、G. Diamantidis、J. Emswiler、H. Fan、R. Neubeck、K.M.R. Pillai、T.R. Wagler、C.-K. Chen、K. Natalie、N. Soundararajan、R.S. Ranganathan

  DOI：10.1016/0040-4020(96)00668-0

  日期：1996.8

  The synthesis of 2,4,6-triiodoisophthalamides substituted by a lactam moiety is described. A tandem ring opening-ring closure methodology consisting of a regiospecific ether cleavage of the tetrahydrofuroanilide 14b, followed by lactamization to α-oxygenated anilides 15b or 16b, gave α-O-functionalized-δ-valerolactams 12b or 13b, respectively. This approach is also compatible with the presence of ester

  描述了被内酰胺​​部分取代的2,4,6-三碘间苯二甲酰胺的合成。串联开环开环方法由四氢呋喃苯胺14b的区域特异性醚裂解，然后内酰胺化为α-氧化的酸酐15b或16b组成，分别得到α-O-官能化的δ-戊内酰胺12b或13b。该方法也与三碘苯基部分上酯和羰基氯官能团的存在兼容。还实现了内酰胺34–39的一般合成。进一步的化学修饰导致了水溶性的未取代内酰胺（34d，35d，37d）和α-羟基内酰胺[ 42（d，e），13（d，e）作为X射线造影剂而感兴趣的是图43和43 ]。
• 2,4,6-triiodo-1,3-benzenedicarboxylic acid compounds used as
  申请人：Bracco International B.V.

  公开号：US05463080A1

  公开（公告）日：1995-10-31

  Compounds, useful as radiolabeling reagents, including a trihalogenated phenyl ring and having the formula ##STR1## wherein X.sub.1, X.sub.2 and X.sub.3 are halogens, one of which may be a radiohalogen, are disclosed. The invention further includes radiohalogenated proteins as well as processes for preparing such reagents and radiohalogenated proteins.

  作为放射标记试剂有用的化合物，包括一个三卤代苯环，化学式为##STR1## 其中X.sub.1、X.sub.2和X.sub.3是卤素，其中一个可能是放射性卤素。该发明还包括放射性卤代蛋白以及制备这种试剂和放射性卤代蛋白的方法。
• 一种碘普罗胺的制备方法
  申请人：山东诚汇双达药业有限公司

  公开号：CN106699594B

  公开（公告）日：2018-11-06

  本发明属于化学合成技术领域，具体涉及一种碘普罗胺的制备方法。以5‑氨基‑2,4,6‑三碘异酞酸为原料制得二酯化物，与甲氧基乙酰氯反应，再分别与侧链3‑氨基丙二醇、3‑甲基氨基丙二醇进行酯的氨解反应得到碘普罗胺。本发明的碘普罗胺的制备方法，催化剂及副产物甲醇只需溶剂结晶即可除去，可以实现绿色生产，无三废排放，特别适合于工业化大生产制备碘普罗胺。
• 制备碘比醇的方法、其中间体及其制备方法
  申请人：苏州科伦药物研究有限公司

  公开号：CN110903275A

  公开（公告）日：2020-03-24

  本发明公开了制备碘比醇的方法、其中间体及其制备方法。具体公开了一种用于制备碘比醇的中间体M1 5‑(2‑异丙基‑1,3‑二氧己环‑5‑羰酰基)‑2,4,6‑三碘间苯二甲酸。此外，本发明还公开了所述中间体M1的制备方法以及由该中间体制备碘比醇的方法。本发明的中间体活性高、易制备，由该中间体合成碘比醇的方法时间短，合成方法简单，综合成本低，且反应目标物的产率和纯度高，因此适用于工业化生产。
• 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：——