5-(3,4-dimethyl-pyrrol-2-ylmethylene)-3,4-dimethyl-1,5-dihydro-pyrrol-2-one | 51471-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(3,4-dimethyl-pyrrol-2-ylmethylene)-3,4-dimethyl-1,5-dihydro-pyrrol-2-one
• 英文别名: 3,4,3',4'-Tetramethyl-5'-oxo-1',5'-dihydro-dipyrro-methen-(2,2')；3,4,3',4'-Tetramethyl-5'-oxo-1',5'-dihydro-dipyrromethen-(2,2')；5-[(3,4-dimethyl-1H-pyrrol-2-yl)methylidene]-3,4-dimethylpyrrol-2-one
• CAS: 51471-22-8
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: YVITXEKAHYETRK-UHFFFAOYSA-N

物化性质

• 沸点：
  462.1±45.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(3,4-dimethyl-pyrrol-2-ylmethylene)-3,4-dimethyl-1,5-dihydro-pyrrol-2-one 在 sodium tetrahydroborate 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 38.5h， 生成 (4Z,20Z)-2,3,7,8,17,18,22,23-octamethyl-12,13-bis(2-carboxyethyl)-1H,10H,15H,24H,25H,26H,27H,28H,29H-pentapyrrin-1,24-dione
  参考文献：
  名称：

  分子内氢键和线性五吡咯构象。

  摘要：

  三种新的线性五吡咯红宝石类似物：2,3,7,8,17,18,22,23-octamethyl-12,13-bis-(2-carboxyethyl)-1,10,15,24,25,27,28 ,29-八氢-27H-pentapyrrin-1,24-dione 和 2,3,8,12,13,17,22,23-octamethyl-7,18-bis-(2-carboxyethyl)-1,10,15 ,24,25,26,27,28, 29-octahydro-27H-pentapyrrin-1,24-dione 及其 7,18-二己酸类似物分别由 2,3,7,8-四甲基- (10H)-dipyrrin-2-one，来自 2,3,8-trimethyl-7-[2-(甲氧基羰基)乙基]-(10H)-dipyrrinone，和 2,3,8-trimethyl-7-[5- (甲氧基羰基)戊基]-(10H)-二吡啉酮。(CD3)2SO

  DOI：

  10.1007/s00706-014-1198-5
• 作为产物：
  描述：

  3,4-dimethyl-3-pyrrolin-2-one 、 3,4-二甲基-1H-吡咯-2-羧醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以52%的产率得到5-(3,4-dimethyl-pyrrol-2-ylmethylene)-3,4-dimethyl-1,5-dihydro-pyrrol-2-one
  参考文献：
  名称：

  Methoxyl-induced fluorescence quenching in N,N′-bridged 9H-dipyrrinones and an X-ray crystal structure

  摘要：

  Strongly fluorescent dipyrrinones can be prepared by bridging the pyrrole and lactam nitrogens with a carbonyl group, from reaction with N,N'-carbonyldiimidazole in the presence of a strong, non-nucleophilic base. The yellow, N,N'-carbonyl-bridged dipyrrinones typically have fluorescent quantum yields (phi(F)) approaching 1.0. Thus, in chloroform, N,N'-bridged 9H-dipyrrinones with beta-alkyl substituents: 2,3-diethyl-7,8-dimethyl has phi(F) = 0.90 (lambda(em) = 465 nm) and 2,3-dimethyl-7,8-dimethoxy has phi(F) = 0.84 (lambda(em) = 482 nm). In contrast, 2,3-dimethoxy-7,8-dimethyl and 2,3,7,8-tetramethoxy show red-shifted lambda(em) but with strongly reduced phi(F): phi(F) = 0.10 (lambda(em) = 511 nm) and 0.08 (lambda(em) = 511 nm), respectively. Methoxy substituents on the lactam, but not the pyrrole ring act to quench the fluorescence and shift the emission and excitation wavelengths bathochromically. The first X-ray crystal structure of an N,N'-carbonyl-bridged dipyrrinone was obtained from 7,8-dimethoxy-2,3-dimethyl-10H-dipyrrin-1-one.

  DOI：

  10.1007/s00706-008-0924-2