(E)-4-nitrophenyl 3-(4-bromophenyl)but-2-enoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-nitrophenyl 3-(4-bromophenyl)but-2-enoate
• 英文别名: (4-nitrophenyl) (E)-3-(4-bromophenyl)but-2-enoate
• 化学式: C₁₆H₁₂BrNO₄
• 分子量: 362.18
• InChiKey: AHKVKAZFJBFUBJ-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-nitrophenyl 3-(4-bromophenyl)but-2-enoate 、 Glyoxylsaeure-aethylester-benzoylhydrazon 在 C₁₈H₂₆N₃⁽¹⁺⁾*C₂H₆BF₂^(1-) 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以91%的产率得到(R)-ethyl 1-benzamido-4-(4-bromophenyl)-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylate
  参考文献：
  名称：

  Organocatalytic Enantioselective γ-Aminoalkylation of Unsaturated Ester: Access to Pipecolic Acid Derivatives

  摘要：

  The direct gamma-carbon functionalization of alpha,beta-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic gamma-carbon undergoes highly enantioselective additions to hydrazones. The resulting delta-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.

  DOI：

  10.1021/ol402358k
• 作为产物：
  描述：

  3-(4-bromophenyl)but-2-enoic acid ethyl ester 在 4-二甲氨基吡啶 、 水 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 生成 (E)-4-nitrophenyl 3-(4-bromophenyl)but-2-enoate
  参考文献：
  名称：

  Organocatalytic Enantioselective γ-Aminoalkylation of Unsaturated Ester: Access to Pipecolic Acid Derivatives

  摘要：

  The direct gamma-carbon functionalization of alpha,beta-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic gamma-carbon undergoes highly enantioselective additions to hydrazones. The resulting delta-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.

  DOI：

  10.1021/ol402358k

文献信息

• Organocatalytic Enantioselective γ-Aminoalkylation of Unsaturated Ester: Access to Pipecolic Acid Derivatives
  作者：Jianfeng Xu、Zhichao Jin、Yonggui Robin Chi

  DOI：10.1021/ol402358k

  日期：2013.10.4

  The direct gamma-carbon functionalization of alpha,beta-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic gamma-carbon undergoes highly enantioselective additions to hydrazones. The resulting delta-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.