5,6,7,8-tetramethyl-N-tert-butyloxycarbonyl-azabenzonorbornadiene | 885691-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,6,7,8-tetramethyl-N-tert-butyloxycarbonyl-azabenzonorbornadiene
• 英文别名: Tert-butyl 3,4,5,6-tetramethyl-11-azatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-11-carboxylate；tert-butyl 3,4,5,6-tetramethyl-11-azatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-11-carboxylate
• CAS: 885691-67-8
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: MLKLRSVRAMPDQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6,7,8-tetramethyl-N-tert-butyloxycarbonyl-azabenzonorbornadiene 在 palladium on activated charcoal 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 吡啶 、 (S,S)-(R,R)-C₂-ferriphos-tolyl 、 甲酸铵 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 144.0h， 生成 (1S,2S)-(2-benzoylamino-1,2,3,4-tetrahydro-5,6,7,8-tetramethylnaphthalen-1-yl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of chiral 1,2-diamines by the catalytic ring opening of azabenzonorbornadienes: application in the preparation of new chiral ligands

  摘要：

  In the presence of a rhodium catalyst (5 mol %) generated in situ from [Rh(cod)C]12 and (S,S')-(R,R')-C-2-ferriphos-tolyl, the asymmetric ring-opening reaction of N-Boc-azabenzonorbornadienes with dibenzylamine proceeded with excellent enantioselectivity (up to > 99% ee) to give the corresponding 1,2-diamine scaffolds in high yields. The sequential deprotection of the ring-opened products and treatment with tartaric acid gave the enantiomerically pure 1.2-diamine tartrate salts. These salts were used for the preparation of new chiral ligands Such as the salen-type ligands and Trost-type ligands, (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.024
• 作为产物：
  描述：

  1-吡咯甲酸叔丁酯 、 1,2-二溴-3,4,5,6-四氢甲基苯 在 正丁基锂 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 48.0h， 以34%的产率得到5,6,7,8-tetramethyl-N-tert-butyloxycarbonyl-azabenzonorbornadiene
  参考文献：
  名称：

  Enantioselective synthesis of chiral 1,2-diamines by the catalytic ring opening of azabenzonorbornadienes: application in the preparation of new chiral ligands

  摘要：

  In the presence of a rhodium catalyst (5 mol %) generated in situ from [Rh(cod)C]12 and (S,S')-(R,R')-C-2-ferriphos-tolyl, the asymmetric ring-opening reaction of N-Boc-azabenzonorbornadienes with dibenzylamine proceeded with excellent enantioselectivity (up to > 99% ee) to give the corresponding 1,2-diamine scaffolds in high yields. The sequential deprotection of the ring-opened products and treatment with tartaric acid gave the enantiomerically pure 1.2-diamine tartrate salts. These salts were used for the preparation of new chiral ligands Such as the salen-type ligands and Trost-type ligands, (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.024

文献信息

• Enantioselective synthesis of chiral 1,2-diamines by the catalytic ring opening of azabenzonorbornadienes: application in the preparation of new chiral ligands
  作者：Yong-Hwan Cho、Aude Fayol、Mark Lautens

  DOI：10.1016/j.tetasy.2005.12.024

  日期：2006.2

  In the presence of a rhodium catalyst (5 mol %) generated in situ from [Rh(cod)C]12 and (S,S')-(R,R')-C-2-ferriphos-tolyl, the asymmetric ring-opening reaction of N-Boc-azabenzonorbornadienes with dibenzylamine proceeded with excellent enantioselectivity (up to > 99% ee) to give the corresponding 1,2-diamine scaffolds in high yields. The sequential deprotection of the ring-opened products and treatment with tartaric acid gave the enantiomerically pure 1.2-diamine tartrate salts. These salts were used for the preparation of new chiral ligands Such as the salen-type ligands and Trost-type ligands, (c) 2006 Elsevier Ltd. All rights reserved.