(1S,2R,3S,4R)-N-(2-(diphenylphosphino)benzyl)-3-ethoxy-N-ethyl-4,7,7-trimethylbicyclo[2.2.1]heptan-2-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,3S,4R)-N-(2-(diphenylphosphino)benzyl)-3-ethoxy-N-ethyl-4,7,7-trimethylbicyclo[2.2.1]heptan-2-amine
• 英文别名: (1S,2R,3S,4R)-N-[(2-diphenylphosphanylphenyl)methyl]-3-ethoxy-N-ethyl-4,7,7-trimethylbicyclo[2.2.1]heptan-2-amine
• 化学式: C₃₃H₄₂NOP
• 分子量: 499.676
• InChiKey: VKCXUHXMWMGBKC-TXLSGFARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氨基-1,7,7-三甲基-双环[2,2,1]庚-2-醇 在 正丁基锂 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 27.0h， 生成 (1S,2R,3S,4R)-N-(2-(diphenylphosphino)benzyl)-3-ethoxy-N-ethyl-4,7,7-trimethylbicyclo[2.2.1]heptan-2-amine
  参考文献：
  名称：

  Camphane-based aminophosphine ligands for Pd-catalyzed asymmetric allylic alkylation

  摘要：

  A practical synthesis of new chiral aminophosphine ligands based on the camphane scaffold bearing alkoxy groups was accomplished. The application of these ligands in the Pd-catalyzed allylic alkylation of (E)-1,3-diphenyl-2-propenyl acetate proceeded with excellent conversions and ee's of up to 91%. Variation of the alkoxy substituents did not substantially influence the catalytic performance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.003
• 作为试剂：
  描述：

  (±)-反式-1,3-二苯基烯丙基乙酸酯 、 丙二酸二甲酯 在 bis(η3-allyl-μ-chloropalladium(II)) 、 (1S,2R,3S,4R)-N-(2-(diphenylphosphino)benzyl)-3-ethoxy-N-ethyl-4,7,7-trimethylbicyclo[2.2.1]heptan-2-amine 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到(R)-methyl 2-carbomethoxy-3,5-diphenylpent-4-enoate
  参考文献：
  名称：

  Camphane-based aminophosphine ligands for Pd-catalyzed asymmetric allylic alkylation

  摘要：

  A practical synthesis of new chiral aminophosphine ligands based on the camphane scaffold bearing alkoxy groups was accomplished. The application of these ligands in the Pd-catalyzed allylic alkylation of (E)-1,3-diphenyl-2-propenyl acetate proceeded with excellent conversions and ee's of up to 91%. Variation of the alkoxy substituents did not substantially influence the catalytic performance. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.003

文献信息

• Camphane-based aminophosphine ligands for Pd-catalyzed asymmetric allylic alkylation
  作者：Irena Philipova、Georgi Stavrakov、Vladimir Dimitrov

  DOI：10.1016/j.tetasy.2013.09.003

  日期：2013.10

  A practical synthesis of new chiral aminophosphine ligands based on the camphane scaffold bearing alkoxy groups was accomplished. The application of these ligands in the Pd-catalyzed allylic alkylation of (E)-1,3-diphenyl-2-propenyl acetate proceeded with excellent conversions and ee's of up to 91%. Variation of the alkoxy substituents did not substantially influence the catalytic performance. (C) 2013 Elsevier Ltd. All rights reserved.