dimethyl 2-(2-(azepan-1-yl)benzylidene)malonate | 1097259-57-8

• 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: dimethyl 2-(2-(azepan-1-yl)benzylidene)malonate
• CAS: 1097259-57-8
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: RSMNEKTWVVSKAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(2-(azepan-1-yl)benzylidene)malonate 在 gadolinium(III) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以82%的产率得到dimethyl 6a,7,8,9,10,11-hexahydroazepino[1,2-a]quinoline-6,6(5H)-dicarboxylate
  参考文献：
  名称：

  Lewis Acid Catalyzed Formation of Tetrahydroquinolines via an Intramolecular Redox Process

  摘要：

  Polycyclic tetrahydroquinolines were prepared by an efficient Lewis acid catalyzed 1,5-hydride shift, ring closure sequence. Gadolinium triflate was Identified as a catalyst that Is superior to scandium triflate as well as other Lewis acids. An approach toward a catalytic enantioselective variant Is also described.

  DOI：

  10.1021/ol802519r
• 作为产物：
  描述：

  2-(azepan-1-yl)benzaldehyde 、 丙二酸二甲酯 在 哌啶 、 苯甲酸 作用下， 以 苯 为溶剂， 反应 1.5h， 以95%的产率得到dimethyl 2-(2-(azepan-1-yl)benzylidene)malonate
  参考文献：
  名称：

  Lewis Acid Catalyzed Formation of Tetrahydroquinolines via an Intramolecular Redox Process

  摘要：

  Polycyclic tetrahydroquinolines were prepared by an efficient Lewis acid catalyzed 1,5-hydride shift, ring closure sequence. Gadolinium triflate was Identified as a catalyst that Is superior to scandium triflate as well as other Lewis acids. An approach toward a catalytic enantioselective variant Is also described.

  DOI：

  10.1021/ol802519r

文献信息

• Catalytic Enantioselective tert-Aminocyclization by Asymmetric Binary Acid Catalysis (ABC): Stereospecific 1,5-Hydrogen Transfer
  作者：Liujuan Chen、Long Zhang、Jian Lv、Jin-Pei Cheng、Sanzhong Luo

  DOI：10.1002/chem.201201532

  日期：2012.7.16

  Selective H transfer by ABC: A new asymmetric binary acid catalyst was developed to promote 1,5‐H transfer specifically and stereoselectively in tert‐aminocyclization reactions with excellent activity, high enantioselectivity, and broad substrate scope. The H atom (in red) was proven to transfer through a stereospecific suprafacial pathway (see scheme).

  通过ABC进行的选择性H转移：开发了一种新型的不对称二元酸催化剂，可在叔氨基环化反应中特异性和立体选择性地促进1,5-H转移，具有出色的活性，高对映选择性和广泛的底物范围。事实证明，H原子（红色）通过立体特异性表面途径转移（参见方案）。