1-isopropyl-4-phenyl-3-pyrrolin-2-one | 178382-42-8

• 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: 1-isopropyl-4-phenyl-3-pyrrolin-2-one
• 英文别名: 3-phenyl-1-propan-2-yl-2H-pyrrol-5-one
• CAS: 178382-42-8
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: IRQUZYQYUKSRSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-isopropyl-4-phenyl-3-pyrrolin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、400.0 kPa 条件下， 反应 20.0h， 以68%的产率得到1-isopropyl-4-phenylpyrrolidin-2-one
  参考文献：
  名称：

  环丁酮的新扩环：吡咯啉酮、吡咯烷和吡咯的合成

  摘要：

  2,2-二氯环丁酮与各种胺反应开环，生成 4,4-二氯丁酰胺。这些化合物被证明是合成 3-吡咯啉-2-酮、2-吡咯烷酮、吡咯烷和吡咯的合适底物。

  DOI：

  10.1055/s-2004-822900
• 作为产物：
  描述：

  N-isopropyl-3-phenylpropanamidate 在 仲丁基锂 、 silica gel 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.83h， 生成 1-isopropyl-4-phenyl-3-pyrrolin-2-one
  参考文献：
  名称：

  Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides:  Diastereoselective and Enantioselective Substitutions

  摘要：

  The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity, Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.

  DOI：

  10.1021/jo952223r

文献信息

• New Ring Expansion of Cyclobutanones: Synthesis of Pyrrolinones, ­Pyrrolidines and Pyrroles
  作者：Norbert De Kimpe、Guido Verniest、Stefaan Boterberg、Filip Bombeke、Christian V. Stevens

  DOI：10.1055/s-2004-822900

  日期：——

  2-Dichlorocyclobutanones reacted with various amines to give ring opening leading to 4,4-dichlorobutanamides. These compounds proved to be suitable substrates for the synthesis of 3-pyrrolin-2-ones, 2-pyrrolidinones, pyrrolidines and pyrroles.

  2,2-二氯环丁酮与各种胺反应开环，生成 4,4-二氯丁酰胺。这些化合物被证明是合成 3-吡咯啉-2-酮、2-吡咯烷酮、吡咯烷和吡咯的合适底物。
• Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides:  Diastereoselective and Enantioselective Substitutions
  作者：Gary P. Lutz、Hua Du、Donald J. Gallagher、Peter Beak

  DOI：10.1021/jo952223r

  日期：1996.1.1

  The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity, Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.