2-bromo-N-((1S,2R,3S,4R)-3-ethoxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-N-ethylbenzamide | 1393881-32-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-bromo-N-((1S,2R,3S,4R)-3-ethoxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-N-ethylbenzamide
• CAS: 1393881-32-7
• 化学式: C₂₁H₃₀BrNO₂
• 分子量: 408.379
• InChiKey: AVCLQZYBLSACJQ-FLTJSSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-bromo-N-((1S,2R,3S,4R)-3-ethoxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-N-ethylbenzamide 、 二环己基氯化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以52%的产率得到2-dicyclohexylphosphanyl-N-[(1S,2R,3S,4R)-3-ethoxy-4,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]-N-ethylbenzamide
  参考文献：
  名称：

  Camphane-based phosphino-carboxamide ligands as P,O-chelates in Pd-catalyzed enantioselective allylic alkylation

  摘要：

  A practical synthesis for new chiral phosphino-carboxamide ligands has been accomplished. These ligands were effectively modified both on the amide moiety and the phosphine atom. Application of these ligands in the Pd-catalyzed allylic alkylation of (E)-1,3-diphenyl-2-propenyl acetate proceeded with excellent conversions and with ee's of up to 92%. The use of a camphane based chiral auxiliary was found to be crucial for the asymmetric induction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.012
• 作为产物：
  描述：

  、 碘乙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以81%的产率得到2-bromo-N-((1S,2R,3S,4R)-3-ethoxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)-N-ethylbenzamide
  参考文献：
  名称：

  Camphane-based phosphino-carboxamide ligands as P,O-chelates in Pd-catalyzed enantioselective allylic alkylation

  摘要：

  A practical synthesis for new chiral phosphino-carboxamide ligands has been accomplished. These ligands were effectively modified both on the amide moiety and the phosphine atom. Application of these ligands in the Pd-catalyzed allylic alkylation of (E)-1,3-diphenyl-2-propenyl acetate proceeded with excellent conversions and with ee's of up to 92%. The use of a camphane based chiral auxiliary was found to be crucial for the asymmetric induction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.012