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

文献信息

• Methoxyl-induced fluorescence quenching in N,N′-bridged 9H-dipyrrinones and an X-ray crystal structure
  作者：Sanjeev K. Dey、David A. Lightner

  DOI：10.1007/s00706-008-0924-2

  日期：2008.11

  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.
• Intramolecular hydrogen bonding and linear pentapyrrole conformation
  作者：D. Timothy Anstine、David A. Lightner

  DOI：10.1007/s00706-014-1198-5

  日期：2014.7

  0H)-dipyrrinone. 13C NMR and 1H NMR measurements in (CD3)2SO confirmed the pentapyrrole structures, while 1H NMR data indicate intramolecular hydrogen bonding between the CO2H and dipyrrinone groups. Molecular mechanics modeling studies suggest stable U-shape conformations capable of encapsulating small planar aromatic molecules.

  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