4-Acetamino-3-penten-2-on | 23652-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Acetamino-3-penten-2-on
• 英文别名: N-(4-oxopent-2-en-2-yl)acetamide
• CAS: 23652-91-7；150172-09-1；1118-83-8
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: QMGDSBNNZBOUIV-UHFFFAOYSA-N

物化性质

• 沸点：
  315.0±34.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Acetamino-3-penten-2-on 、 林可霉素 2,7-二乙酸酯 在 十羰基二铼 作用下， 以 正辛烷 为溶剂， 反应 24.0h， 以68%的产率得到3,4-bis(4-methoxyphenyl)-2,6-dimethylpyridine
  参考文献：
  名称：

  Rhenium-Catalyzed Regioselective Synthesis of Multisubstituted Pyridines from β-Enamino Ketones and Alkynes via C–C Bond Cleavage

  摘要：

  A new method is described for the regioselective synthesis of multisubstituted pyridine derivatives. Treatment of N-acetyl beta-enamino ketones with alkynes in the presence of the rhenium catalyst, Re-2(CO)(10), gives multisubstituted pyridines regioselectively. In this reaction, the N-acetyl moieties are important for the selective formation of the multisubstituted pyridines. This reaction proceeds via insertion of alkynes into a carbon carbon single bond of beta-enamino ketones, intramolecular nucleophilic cyclization, and elimination of acetic acid.

  DOI：

  10.1021/ol301273j

文献信息

• Rhenium-Catalyzed Regioselective Synthesis of Multisubstituted Pyridines from β-Enamino Ketones and Alkynes via C–C Bond Cleavage
  作者：Shun-ichi Yamamoto、Kana Okamoto、Makiko Murakoso、Yoichiro Kuninobu、Kazuhiko Takai

  DOI：10.1021/ol301273j

  日期：2012.6.15

  A new method is described for the regioselective synthesis of multisubstituted pyridine derivatives. Treatment of N-acetyl beta-enamino ketones with alkynes in the presence of the rhenium catalyst, Re-2(CO)(10), gives multisubstituted pyridines regioselectively. In this reaction, the N-acetyl moieties are important for the selective formation of the multisubstituted pyridines. This reaction proceeds via insertion of alkynes into a carbon carbon single bond of beta-enamino ketones, intramolecular nucleophilic cyclization, and elimination of acetic acid.