1-(2,2-dibromovinyl)pyrrolidin-2-one | 1359971-29-1

• 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: 1-(2,2-dibromovinyl)pyrrolidin-2-one
• 英文别名: 1-(2,2-Dibromoethenyl)pyrrolidin-2-one；1-(2,2-dibromoethenyl)pyrrolidin-2-one
• CAS: 1359971-29-1
• 化学式: C₆H₇Br₂NO
• 分子量: 268.936
• InChiKey: QQCALLMEVCXCAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-(2,2-dibromovinyl)pyrrolidin-2-one 在 四(三苯基膦)钯 、 三正丁基氢锡 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以88%的产率得到(Z)-1-(2-bromovinyl)pyrrolidin-2-one
  参考文献：
  名称：

  Protecting Group Free, Stereocontrolled Synthesis of β-Halo-enamides

  摘要：

  Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of beta-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol.

  DOI：

  10.1021/jo202130e
• 作为产物：
  描述：

  2-氧吡咯烷-1-甲醛 、 溴甲基三苯基溴化磷 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以94%的产率得到1-(2,2-dibromovinyl)pyrrolidin-2-one
  参考文献：
  名称：

  Protecting Group Free, Stereocontrolled Synthesis of β-Halo-enamides

  摘要：

  Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of beta-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol.

  DOI：

  10.1021/jo202130e

文献信息

• Protecting Group Free, Stereocontrolled Synthesis of β-Halo-enamides
  作者：Adele E. Pasqua、James J. Crawford、De-Liang Long、Rodolfo Marquez

  DOI：10.1021/jo202130e

  日期：2012.3.2

  Enamides, dienamides, and enynamides are important building blocks in synthetic, biological, and medicinal chemistry as well as materials science. Despite the extensive breath of their potential utility in synthetic chemistry, there is a lack of simple, high-yielding methods to deliver them efficiently and as single isomers. In this paper, we present a novel, protecting group free, efficient, and stereoselective approach to the generation of beta-halo-enamides. The methodology presented provides a robust synthetic platform from which E- or Z-enamides can be generated in good yields and with complete stereocontrol.