4-tetrahydro-1H-pyrrol-1-ylpent-3-en-2-one | 255846-01-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-tetrahydro-1H-pyrrol-1-ylpent-3-en-2-one
• 英文别名: (Z)-4-pyrrolidin-1-ylpent-3-en-2-one
• CAS: 255846-01-6
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: CWUMGRRVCLAYKC-FPLPWBNLSA-N

物化性质

• 沸点：
  248.4±19.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-tetrahydro-1H-pyrrol-1-ylpent-3-en-2-one 在 silica gel 作用下， 反应 0.2h， 以90%的产率得到1-乙酰基吡咯烷
  参考文献：
  名称：

  Synthesis in dry media coupled with microwave irradiation : Application to the preparation of enaminoketones.

  摘要：

  Beta-diketones react with a variety of amines and aminoesters over clay K10 or silica under microwave irradiation in open vessels to give within a few minutes, the corresponding enaminoketones with good yields. According to the reaction conditions acylamines may also result.

  DOI：

  10.1016/s0040-4039(00)60678-0
• 作为产物：
  描述：

  四氢吡咯 、 乙酰丙酮 反应 0.17h， 以98%的产率得到4-tetrahydro-1H-pyrrol-1-ylpent-3-en-2-one
  参考文献：
  名称：

  Synthesis in dry media coupled with microwave irradiation : Application to the preparation of enaminoketones.

  摘要：

  Beta-diketones react with a variety of amines and aminoesters over clay K10 or silica under microwave irradiation in open vessels to give within a few minutes, the corresponding enaminoketones with good yields. According to the reaction conditions acylamines may also result.

  DOI：

  10.1016/s0040-4039(00)60678-0

文献信息

• Reactions of Enamines with Selectfluor:  A Straightforward Route to Difluorinated Carbonyl Compounds
  作者：Weimin Peng、Jean'ne M. Shreeve

  DOI：10.1021/jo0506837

  日期：2005.7.1

  Reactions of enamines, preformed from β-dicarbonyl and monocarbonyl compounds, with Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) under mild conditions (triethylamine (TEA) or molecular sieves) easily led to the corresponding difluorinated carbonyl compounds in high yields.

  在温和条件下（三乙胺（TEA）或分子筛），由β-二羰基和单羰基化合物形成的烯胺与Selectfluor（1-氯甲基-4-氟-1,4-二氮杂双环[2.2.2]辛烷双（四氟硼酸酯）的反应）容易以高收率得到相应的二氟羰基化合物。
• Efficient synthesis of tetrasubstituted thiophenes by reaction of benzoyl isothiocyanates, ethyl bromopyruvate and enaminones
  作者：Issa Yavari、Zinatossadat Hossaini、Maryam Sabbaghan

  DOI：10.1016/j.tetlet.2007.11.174

  日期：2008.1

  An efficient synthesis of ethyl 2-(4-acetyl-5-benzoylamino-3-methyl-2-thienyl)-2-oxoacetates is described via reaction between benzoyl isothiocyanates and ethyl bromopyruvate in the presence of enaminones.

  通过在烯胺酮的存在下，苯甲酰基异硫氰酸酯与溴丙酮酸乙酯之间的反应，描述了2-（4-乙酰基-5-苯甲酰基氨基-3-甲基-2-噻吩基）-2-氧乙酸乙酯的有效合成。
• Regioselective Synthesis of 2(1<i>H</i>)-Pyridinones from β-Aminoenones and Malononitrile. Reaction Mechanism
  作者：Angel Alberola、Luis A. Calvo、Alfonso González Ortega、M. Carmen Sañudo Ruíz、Pedro Yustos、Santiago García Granda、Esther García-Rodriguez

  DOI：10.1021/jo991121o

  日期：1999.12.1

  The identification of some intermediates of the reactions between beta-aminoenones and malononitrile to give 2(1H)-pyridinones has allowed us to obtain valuable information concerning its mechanism. These reactions begin with a conjugated addition of the nitrile to the enone followed by elimination. The compounds thus obtained cyclize to nonisolable 2H-pyran-2-imine. This afforded 2(1H)-pyridinones by ring opening to unsaturated aminoamides followed by cyclization (Dimroth-type rearrangement).
• US4835268A
  申请人：——

  公开号：US4835268A

  公开（公告）日：1989-05-30
• Synthesis in dry media coupled with microwave irradiation : Application to the preparation of enaminoketones.
  作者：Benno Rechsteiner、Françoise Texier-Boullet、Jack Hamelin

  DOI：10.1016/s0040-4039(00)60678-0

  日期：1993.8

  Beta-diketones react with a variety of amines and aminoesters over clay K10 or silica under microwave irradiation in open vessels to give within a few minutes, the corresponding enaminoketones with good yields. According to the reaction conditions acylamines may also result.