N,N-dimethyl-N-[2-(dimethylaminomethylene)amino-3-dimethylamino]prop-2-enylideneammonium perchlorate | 50704-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: N,N-dimethyl-N-[2-(dimethylaminomethylene)amino-3-dimethylamino]prop-2-enylideneammonium perchlorate
• 英文别名: 1,3-bis-dimethylamino-2-(dimethylamino-methyleneamino)-trimethinium; perchlorate；N-(3-(dimethylamino)-2-((dimethylamino)methyleneamino)allylidene)-N-methylmethanaminium perchlorate；C10H21ClN4O4；[3-(dimethylamino)-2-(dimethylaminomethylideneamino)prop-2-enylidene]-dimethylazanium;perchlorate
• CAS: 50704-19-3
• 化学式: C₁₀H₂₁N₄*ClO₄
• 分子量: 296.754
• InChiKey: LOETWRXQTHIJFD-UHFFFAOYSA-M

物化性质

• 熔点：
  144-146 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -4.43
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  96.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-N-[2-(dimethylaminomethylene)amino-3-dimethylamino]prop-2-enylideneammonium perchlorate 生成 diazomalonaldehyde
  参考文献：
  名称：

  Arnold,Z.; Sauliova,J., Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 2641 - 2647

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-dimethyl-N-[2-(dimethylaminomethylene)amino-3-dimethylamino]prop-2-enylideneammonium diperchlorate 在 三乙胺 作用下， 以 乙醇 为溶剂， 以78.5%的产率得到N,N-dimethyl-N-[2-(dimethylaminomethylene)amino-3-dimethylamino]prop-2-enylideneammonium perchlorate
  参考文献：
  名称：

  Stereoselective control in the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents: experimental investigation and theoretical rationalization

  摘要：

  通过确定产物立体化学和基于密度泛函理论（DFT）的计算，实验上研究了涉及带有电子受体取代基的单取代乙烯酮的斯陶丁格反应的立体选择性。结果表明，亚胺优先攻击乙烯酮上立体障碍较小的外侧，生成内鎓离子中间体。随后，对于环状亚胺，中间体直接进行协同环合反应生成β-内酰胺；而对于线性亚胺，中间体的亚胺部分异构化为更稳定的中间体，后者进一步进行协同环合反应，产生反式β-内酰胺。在实际涉及带有电子受体取代基的单取代乙烯酮的斯陶丁格反应中，立体障碍和异构化而不是扭曲电子效应在控制立体选择性中起着关键作用，尽管在理论上，具有强电子受体基团的不可获得的硼乙烯酮通过扭曲电子效应控制立体选择性。

  DOI：

  10.1039/c0ob00783h

文献信息

• Retinoidal Pyrimidinecarboxylic Acids. Unexpected Diaza-Substituent Effects in Retinobenzoic Acids.
  作者：Kiminori OHTA、Emiko KAWACHI、Noriko INOUE、Hiroshi FUKASAWA、Yuichi HASHIMOTO、Akiko ITAI、Hiroyuki KAGECHIKA

  DOI：10.1248/cpb.48.1504

  日期：——

  Several pyridine-and pyrimidine-carboxylic acids were synthesized as ligand candidates for retinoid nuclear receptors, retinoic acid receptors (RARs) and retinoic X receptors (RXRs). Although the pyridine derivatives, 6-[(5, 6, 7, 8-tetrahydro-5, 5, 8, 8-tetramethyl-2-naphthalenyl)carbamoyl]pyridine-3-carboxylic acid (2b) and 6-[(5, 6, 7, 8-tetrahydro-5, 5, 8, 8-tetramethyl-2-naphthalenyl)carboxamido]pyridine-3-carboxylic acid (5b) are more potent than the corresponding benzoic acid-type retinoids, Am80 (2a) and Am580 (5a), the replacement of the benzene ring of Am580 (5a), Am555 (6a), or Am55 (7a) with a pyrimidine ring caused loss of the retinoidal activity both in HL-60 cell differentiation assay and in RAR transactivation assay using COS-1 cells. On the other hand, pyrimidine analogs (PA series, 10 and 11) of potent RXR agonists (retinoid synergists) with a diphenylamine skeleton (DA series, 8 and 9) exhibited potent retinoid synergistic activity in HL-60 cell differentiation assay and activated RXRs. Among the synthesized compounds, 2-[N-n-propyl-N-(5, 6, 7, 8-tetrahydro-5, 5, 8, 8-tetramethyl-2-naphthalenyl)amino]pyrimidene-5-carboxylic acid (PA013, 10e) is most active retinoid synergist in HL-60 assay.

  几种吡啶和嘧啶羧酸被合成为视黄酸核受体、视黄酸受体（RARs）和视黄酸X受体（RXRs）的配体候选物。虽然吡啶衍生物，6-[(5, 6, 7, 8-四氢-5, 5, 8, 8-四甲基-2-萘基)氨基甲酰]吡啶-3-羧酸（2b）和6-[(5, 6, 7, 8-四氢-5, 5, 8, 8-四甲基-2-萘基)羧酰胺]吡啶-3-羧酸（5b）比相应的苯甲酸型视黄酸更有效，如Am80（2a）和Am580（5a），但将Am580（5a）、Am555（6a）或Am55（7a）的苯环替换为嘧啶环会导致视黄酸活性在HL-60细胞分化试验和使用COS-1细胞的RAR转录激活试验中丧失。另一方面，具有二苯胺骨架（DA系列，8和9）的强效RXR激动剂（视黄酸协同剂）的嘧啶类似物（PA系列，10和11）在HL-60细胞分化试验中表现出强效的视黄酸协同活性并激活RXRs。在合成的化合物中，2-[N-正丙基-N-(5, 6, 7, 8-四氢-5, 5, 8, 8-四甲基-2-萘基)氨基]嘧啶-5-羧酸（PA013，10e）在HL-60试验中是最活跃的视黄酸协同剂。
• Expeditious Synthesis of 2,3,6-Trisubstituted 2H-1,3-Oxazin-4(3H)-ones via the Tertiary Amine-Induced Reaction of 2-Diazo-3-oxoalkanals and Imines Under Mild Conditions
  作者：Jiaxi Xu、Hengzhen Qi、Jiantao Zhang

  DOI：10.1055/s-0030-1258439

  日期：2011.3

  A series of 2,3,6-trisubstituted 2H-1,3-oxazin-4(3H)-one derivatives were conveniently synthesized in satisfactory to good yields by the reaction of imines with 2-diazo-3-oxoalkanals in the presence of a catalytic amount of a tertiary amine during several seconds under mild condition. Different bases and α-diazo-β-dicarbonyl compounds were also evaluated and a reaction mechanism is proposed. Compared with the corresponding thermal- and photo-induced­ reactions, the current method is a metal-free, mild, highly regioselective, and more efficient approach for the synthesis of 2H-1,3-oxazin-4(3H)-one derivatives.

  一系列2,3,6-三取代的2H-1,3-噁嗪-4(3H)-酮衍生物通过在温和条件下，几秒钟内，利用少量三烰基胺作为催化剂，使亚胺与2-重氮-3-氧代烷醛反应，方便地合成，产率令人满意至良好。研究了不同的碱和α-重氮-β-二羰基化合物，并提出了反应机理。与相应的热引发和光引发反应相比，目前的方法是一种无金属、温和、高度区域选择性且更高效的合成2H-1,3-噁嗪-4(3H)-酮衍生物的方法。
• [EN] SGC STIMULATORS<br/>[FR] STIMULATEURS DE SGC
  申请人：IRONWOOD PHARMACEUTICALS INC

  公开号：WO2012003405A4

  公开（公告）日：2012-02-23
• Arnold,Z. et al., Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 2633 - 2640
  作者：Arnold,Z. et al.

  DOI：——

  日期：——
• Selective acid hydrolysis of 2-substituted-5-dimethylaminomethyleneaminopyrimidines to 5-amino- and 5-hydroxypyrimidines
  作者：T. A. Kizner、M. A. Mikhaleva、E. S. Serebryakova

  DOI：10.1007/bf00756420

  日期：1990.6