1-benzyl-4,5-dimethylene-2-phenylpiperidine

• 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: 1-benzyl-4,5-dimethylene-2-phenylpiperidine
• 英文别名: 1-Benzyl-4,5-dimethylidene-2-phenylpiperidine；1-benzyl-4,5-dimethylidene-2-phenylpiperidine
• 化学式: C₂₀H₂₁N
• 分子量: 275.393
• InChiKey: QVSZGHBBSWSNOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-4,5-dimethylene-2-phenylpiperidine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 对二甲苯 为溶剂， 反应 72.0h， 生成 dimethyl 3-phenylisoquinoline-6,7-dicarboxylate
  参考文献：
  名称：

  Palladium-Catalyzed [4 + 2] Cycloaddition of Aldimines and 1,4-Dipolar Equivalents via Amphiphilic Allylation

  摘要：

  The combination of Pd catalyst and diethylzinc with triethylborane promotes the amphiphilic allylation of aldimines with 2,3-bismethylenebutane-1,4-diol derivatives to serve as bis-allylic zwitterion species to form 3,4-bismethylenepiperidines via a formal [4 + 2] cycloaddition reaction. 3,4-Bismethylenepiperidine rings are applicable for the synthesis of isoquinoline derivatives via the Diels-Alder reaction followed by an oxidation reaction with DDQ.

  DOI：

  10.1021/ol503614d
• 作为产物：
  描述：

  苄胺 在 bis-triphenylphosphine-palladium(II) chloride 、 三丁基膦 、 diethylzinc 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 48.0h， 生成 1-benzyl-4,5-dimethylene-2-phenylpiperidine
  参考文献：
  名称：

  Palladium-Catalyzed [4 + 2] Cycloaddition of Aldimines and 1,4-Dipolar Equivalents via Amphiphilic Allylation

  摘要：

  The combination of Pd catalyst and diethylzinc with triethylborane promotes the amphiphilic allylation of aldimines with 2,3-bismethylenebutane-1,4-diol derivatives to serve as bis-allylic zwitterion species to form 3,4-bismethylenepiperidines via a formal [4 + 2] cycloaddition reaction. 3,4-Bismethylenepiperidine rings are applicable for the synthesis of isoquinoline derivatives via the Diels-Alder reaction followed by an oxidation reaction with DDQ.

  DOI：

  10.1021/ol503614d

文献信息

• Palladium-Catalyzed [4 + 2] Cycloaddition of Aldimines and 1,4-Dipolar Equivalents via Amphiphilic Allylation
  作者：Goki Hirata、Naoshi Yamada、Shohei Sanada、Gen Onodera、Masanari Kimura

  DOI：10.1021/ol503614d

  日期：2015.2.6

  The combination of Pd catalyst and diethylzinc with triethylborane promotes the amphiphilic allylation of aldimines with 2,3-bismethylenebutane-1,4-diol derivatives to serve as bis-allylic zwitterion species to form 3,4-bismethylenepiperidines via a formal [4 + 2] cycloaddition reaction. 3,4-Bismethylenepiperidine rings are applicable for the synthesis of isoquinoline derivatives via the Diels-Alder reaction followed by an oxidation reaction with DDQ.