2-bromo-N-[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]benzamide | 1393881-40-7

• 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-[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]benzamide
• CAS: 1393881-40-7
• 化学式: C₁₇H₂₂BrNO
• 分子量: 336.272
• InChiKey: MRGOTFASTSIMCQ-ZLENFMNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-bromo-N-[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]benzamide 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2-diphenylphosphanyl-N-ethyl-N-[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]benzamide
  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

文献信息

• Camphane-based phosphino-carboxamide ligands as P,O-chelates in Pd-catalyzed enantioselective allylic alkylation
  作者：Irena Philipova、Georgi Stavrakov、Vladimir Dimitrov

  DOI：10.1016/j.tetasy.2012.06.012

  日期：2012.7

  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.