2,2-bis(1-methyl-1H-pyrrol-2-yl)-1-phenylethanone | 112670-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-bis(1-methyl-1H-pyrrol-2-yl)-1-phenylethanone
• 英文别名: bis(1-methyl-2-pyrrolyl)benzoylmethane；2,2-Bis(1-methylpyrrol-2-yl)-1-phenylethanone
• CAS: 112670-91-4
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: XMOQTWUKBGKRSE-UHFFFAOYSA-N

物化性质

• 沸点：
  444.8±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基吡咯 、 苯乙酮 在 碘 、 二甲基亚砜 、 三氟甲磺酸 作用下， 反应 1.0h， 以66%的产率得到2,2-bis(1-methyl-1H-pyrrol-2-yl)-1-phenylethanone
  参考文献：
  名称：

  I₂–CF₃SO₃H Synergistic Promoted sp³ C–H Bond Diarylation of Aromatic Ketones

  摘要：

  An I-2-CF3SO3H synergistic promoted sp(3) C-H bond diarylation protocol was developed for the synthesis of 2,2-bis(4-(dimethylamino)phenyl)-1-aryl ethanones. The reaction performed well in the absence of any metal and ligand. It integrated three reactions with different mechanisms (iodination, Kornblum oxidation, and hydroarylation) in a single reactor.

  DOI：

  10.1021/ol302613q

文献信息

• Determination of corticoids using pyrrole. V Studies on the colored products.
  作者：HIROSHI TOKUNAGA、MASAYUKI TANNO、TOSHIO KIMURA

  DOI：10.1248/cpb.35.1118

  日期：——

  The mechanism of the color reaction and the structures of the colored products of cortisone (1a) and deoxycorticosterone (2a) with pyrrole were elucidated. In the presence of cupric acetate, la and 2a were converted to the oxidation products (1b and 2b) which have a glyoxal side chain at C (17). For studying the chemical structures of the colored products derived from corticoids, phenylglyoxal (3a) was used as a model compound with a glyoxal side chain. By reacting 3a with pyrrole in hydrochloric acid, di (2-pyrrolyl) benzoylmethane (3b) was produced as an intermediate in the formation of the colored product. Compound 3b was changed to [5- (2-pyrrolyl) -2 (2H) - pyrrolylidene] (2-pyrrolyl) benzoylmethane (3d) by reaction with pyrrole in the presence of cupric acetate and hydrochloric acid. Compound 3d in dichloromethane gave the absorption maximum at 480 nm. Corticoids 1b and 2b were converted to the colored products, 21- [5- (2-pyrrolyl) -2 (2H) - pyrrolylidene] -21- (2-pyrrolyl) -4-pregnene-3, 11, 20-trione (1e) and 21- [5- (2-pyrrolyl) -2 (2H) -pyrrolylidene] -21- (2-pyrrolyl) -4-pregnene-3, 20-dione (2e), by reaction with pyrrole under the above conditions. Corticoids 1e and 2e in dichloromethane gave absorption maxima at 510 and 480 nm, respectively. Corticoid 1e showed fluorescence at 562 nm with excitation at 516 nm.

  阐明了可的松（1a）和脱氧可的松（2a）与吡咯的着色反应机理和着色产物的结构。在醋酸铜存在下，la 和 2a 被转化为氧化产物（1b 和 2b），它们在 C（17）处有乙二醛侧链。为了研究由类皮质激素衍生的有色产物的化学结构，我们使用了具有乙二醛侧链的苯基乙二醛（3a）作为模型化合物。将 3a 与吡咯在盐酸中反应，生成二（2-吡咯基）苯甲酰甲烷（3b），作为形成有色产物的中间体。化合物 3b 与吡咯在醋酸铜和盐酸存在下反应生成 [5- (2-pyrrolyl) -2 (2H) - pyrrolylidene] (2-pyrrolyl) benzoylmethane (3d)。化合物 3d 在二氯甲烷中的最大吸收波长为 480 纳米。皮质类化合物 1b 和 2b 转化为有色产物 21- [5- (2- 吡咯基) -2 (2H) - 吡咯烷亚基] -21- (2- 吡咯基) -4- 孕烯-3，11、20 三酮（1e）和 21- [5- (2-pyrrolyl) -2 (2H) -pyrrolylidene] -21- (2-pyrrolyl) -4-pregnene-3, 20-dione（2e）。皮质类化合物 1e 和 2e 在二氯甲烷中的最大吸收波长分别为 510 纳米和 480 纳米。在 516 纳米波长的激发下，皮质类 1e 在 562 纳米波长处显示出荧光。
• I₂–CF₃SO₃H Synergistic Promoted sp³ C–H Bond Diarylation of Aromatic Ketones
  作者：Yan-ping Zhu、Feng-cheng Jia、Mei-cai Liu、Liu-ming Wu、Qun Cai、Yang Gao、An-xin Wu

  DOI：10.1021/ol302613q

  日期：2012.10.19

  An I-2-CF3SO3H synergistic promoted sp(3) C-H bond diarylation protocol was developed for the synthesis of 2,2-bis(4-(dimethylamino)phenyl)-1-aryl ethanones. The reaction performed well in the absence of any metal and ligand. It integrated three reactions with different mechanisms (iodination, Kornblum oxidation, and hydroarylation) in a single reactor.