methyl 1-benzyl-2,6-dioxopiperidine-3-carboxylate | 1240792-21-5

• 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: methyl 1-benzyl-2,6-dioxopiperidine-3-carboxylate
• CAS: 1240792-21-5
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: XQYBIXTXJLATBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-2,6-dioxopiperidine-3-carboxylate 在 potassium tert-butylate 、 lithium chloride 作用下， 以 氘代二甲亚砜 、 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 (E)-1-benzyl-3-(fluoromethylene)piperidine-2,6-dione
  参考文献：
  名称：

  A Unified Strategy for the Synthesis of Difluoromethyl- and Vinylfluoride-Containing Scaffolds

  摘要：

  Here, we report a general method for the synthesis of quaternary and tertiary difluoromethylated compounds and their vinylfluoride analogues. The strategy, which relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and either a palladium-catalyzed decarboxylative protonation or a Krapcho decarboxylation, is practical, scalable, and high yielding. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.

  DOI：

  10.1021/acs.orglett.9b02887
• 作为产物：
  描述：

  戊烷二酰胺 在 sodium hexamethyldisilazane 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 methyl 1-benzyl-2,6-dioxopiperidine-3-carboxylate
  参考文献：
  名称：

  A Unified Strategy for the Synthesis of Difluoromethyl- and Vinylfluoride-Containing Scaffolds

  摘要：

  Here, we report a general method for the synthesis of quaternary and tertiary difluoromethylated compounds and their vinylfluoride analogues. The strategy, which relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and either a palladium-catalyzed decarboxylative protonation or a Krapcho decarboxylation, is practical, scalable, and high yielding. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.

  DOI：

  10.1021/acs.orglett.9b02887

文献信息

• Stereoselective Spirolactam Synthesis via Palladium Catalyzed Arylative Allene Carbocyclization Cascades
  作者：Meiling Li、Darren J. Dixon

  DOI：10.1021/ol101425y

  日期：2010.9.3

  A diastereoselective arylative carbocyclization of pro-nucleophile-linked allenes with aryl and heteroaryl halides to provide spirocyclic lactam products with moderate to high diastereoselectivities and good yields under Pd(0) catalysis is reported. Being operationally simple and tolerant of multiple points of diversity, this complexity building reaction cascade, in which two new carbon-carbon bonds and one new heterocyclic ring are created, should be of high value in both complex natural product synthesis as well as compound library synthesis.