phenylaminomethylenemalonaldehyde | 135304-93-7

• 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: phenylaminomethylenemalonaldehyde
• 英文别名: 2-(anilinomethylidene)propanedial
• CAS: 135304-93-7
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: ADNOPHPMAWDWKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  C₁₄H₂₁N₃⁽²⁺⁾*2BF₄^(1-) 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 phenylaminomethylenemalonaldehyde
  参考文献：
  名称：

  取代喹啉的高效合成

  摘要：

  将取代的苯胺加到 "乙脒 "双四氟硼酸盐 1 [2-二甲基氨基亚甲基-1,3-双（二甲基亚氨 基）丙烷双四氟硼酸盐]中，然后将生成的亚氨基烯胺盐环化，并水解被掩蔽的醛 2，从而得到相应的 3-甲酰基喹啉 3。虽然已知 1 及其类似的双高氯酸盐与脒的缩合可生成嘧啶，但我们认为这是第一个用 "乙烯脒 "双四氟硼酸盐 1 和苯胺进行喹啉环化反应的实例。

  DOI：

  10.1055/s-2001-15221

文献信息

• QUINOLINE-DERIVED AMIDE MODULATORS OF VANILLOID VR1 RECEPTOR
  申请人：Codd Ellen

  公开号：US20080300236A1

  公开（公告）日：2008-12-04

  This invention is directed to vanilloid receptor VR1 ligands. More particularly, this invention relates to quinoline-derived amides that are potent antagonists or agonists of VR1 which are useful for the treatment and prevention of inflammatory and other pain conditions in mammals.

  这项发明涉及辣椒素受体VR1配体。更具体地说，这项发明涉及喹啉衍生的酰胺，它们是VR1的有效拮抗剂或激动剂，可用于治疗和预防哺乳动物的炎症和其他疼痛症状。
• Arnold, Zdenek; Budesinsky, Milos; Pankova, Magdalena, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 5, p. 1019 - 1031
  作者：Arnold, Zdenek、Budesinsky, Milos、Pankova, Magdalena

  DOI：——

  日期：——
• Condensation of Triformylmethane with Heteroaromatic Amines, Including Nucleic Acid Bases. A Novel Example of Ring-Chain Tautomerism.
  作者：Kari Neuvonen、Carmela Zewi、Harri Lönnberg、Yincai Su、Markku Leskelä、Mika Polamo、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-1137

  日期：——

  Treatment of several heteroaromatic amines, including the nucleic acid bases cytosine and adenine, with triformylmethane in pyridine at 70 degrees C afforded 1:1 condensation products (2-11) that were characterized by H-1 and C-13 NMR spectroscopy. All the compounds were assigned as N-substituted aminomethylenemalonaldehydes, strongly preferring the amino/keto form over the imino/enol tautomer. With cytosine and 1-methylcytosine, unequivocal evidence for ring-chain tautomerism was additionally obtained: intramolecular nucleophilic attack of cytosine N3 to one of the carbonyl carbons results in reversible cyclization to a 4-hydroxy-4H-pyrimido[1,6-a]pyrimidin-6(7H)-one derivative (9b, 10b). In dry methanol the corresponding O-methyl ether (12) was obtained.
• ARNOLD, ZDENEK;BUDESINSKY, MILOS;PANKOVA, MAGDALENA, COLLECT. CZECHOSL. CHEM. COMMUN., 56,(1991) N, C. 1019-1031
  作者：ARNOLD, ZDENEK、BUDESINSKY, MILOS、PANKOVA, MAGDALENA

  DOI：——

  日期：——
• An Efficient Synthesis of Substituted Quinolines
  作者：Norma J. Tom、Elizabeth M. Ruel

  DOI：10.1055/s-2001-15221

  日期：——

  The addition of substituted anilines to ”vinamidinium" bis-tetrafluoroborate salt 1 [2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bis-tetrafluoroborate], followed by cyclization of the resulting imino-eneamine salt and hydrolysis of the masked aldehydes 2, provide the corresponding 3-formyl quinolines 3. While the condensation of both 1 and its analogous bis-perchlorate salt and amidines are known to provide pyrimidines, we believe this is the first example of a quinoline annulation sequence with ”vinamidinium" bis-tetrafluoroborate salt 1 and anilines.

  将取代的苯胺加到 "乙脒 "双四氟硼酸盐 1 [2-二甲基氨基亚甲基-1,3-双（二甲基亚氨 基）丙烷双四氟硼酸盐]中，然后将生成的亚氨基烯胺盐环化，并水解被掩蔽的醛 2，从而得到相应的 3-甲酰基喹啉 3。虽然已知 1 及其类似的双高氯酸盐与脒的缩合可生成嘧啶，但我们认为这是第一个用 "乙烯脒 "双四氟硼酸盐 1 和苯胺进行喹啉环化反应的实例。

表征谱图