tert-butyl (E)-2-oxo-3-(1-((prop-2-ynyloxy)carbonyloxy)ethylidene)piperidine-1-carboxylate | 1446518-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (E)-2-oxo-3-(1-((prop-2-ynyloxy)carbonyloxy)ethylidene)piperidine-1-carboxylate
• CAS: 1446518-39-3
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: ZVEIXPSFWGEUTH-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (E)-2-oxo-3-(1-((prop-2-ynyloxy)carbonyloxy)ethylidene)piperidine-1-carboxylate 、 苯酚 在 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以74%的产率得到tert-butyl 3-acetyl-2-oxo-3-(3-phenoxyprop-1-en-2-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  Catalytic Decarboxylative Alkenylation of Enolates

  摘要：

  A palladium-catalyzed decarboxylative alkenylation of stabilized enolates has been developed, which gives rise to alkenylated dicarbonyl products from enol carbonates regioselectively with concomitant installation of a quaternary all-carbon center. The broad scope of the reaction has been demonstrated by successfully utilizing a range of enolates and external phenol nucleophiles.

  DOI：

  10.1021/ol401729m
• 作为产物：
  描述：

  1-Boc-2-哌啶酮 在 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.42h， 生成 tert-butyl (E)-2-oxo-3-(1-((prop-2-ynyloxy)carbonyloxy)ethylidene)piperidine-1-carboxylate
  参考文献：
  名称：

  Catalytic Decarboxylative Alkenylation of Enolates

  摘要：

  A palladium-catalyzed decarboxylative alkenylation of stabilized enolates has been developed, which gives rise to alkenylated dicarbonyl products from enol carbonates regioselectively with concomitant installation of a quaternary all-carbon center. The broad scope of the reaction has been demonstrated by successfully utilizing a range of enolates and external phenol nucleophiles.

  DOI：

  10.1021/ol401729m