(1R,5S)-3,7-bis(4-methoxybenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-2-one | 1099828-14-4

• 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: (1R,5S)-3,7-bis(4-methoxybenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-2-one
• 英文别名: (1R,5S)-3,7-bis[(4-methoxyphenyl)methyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonan-2-one
• CAS: 1099828-14-4
• 化学式: C₂₂H₂₆N₂O₄
• 分子量: 382.459
• InChiKey: DWCIRUSYUBFVPQ-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,5S)-3,7-bis(4-methoxybenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-2-one 在 氢气 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、350.0 kPa 条件下， 反应 22.0h， 以99%的产率得到(1R,5S)-3-(4-methoxybenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-2-one
  参考文献：
  名称：

  A Flexible Route to Chiral 2-endo-Substituted 9-Oxabispidines and Their Application in the Enantioselective Oxidation of Secondary Alcohols

  摘要：

  A new and flexible route to enantiomerically pure bi- and tricyclic 9-oxabispidines has been developed with use of (1R,5S)-7-methyl-2-oxo-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester as the common late-stage intermediate. The 9-oxabispidines synthesized were evaluated as the chiral ligands in the Pd(II)-catalyzed oxidative kinetic resolution of secondary alcohols giving good to excellent selectivity factors of up to 19.

  DOI：

  10.1021/jo802409x
• 作为产物：
  描述：

  (2S,6S)-6-(methanesulfonyloxymethyl)-4-(4-methoxybenzyl)morpholine-2-carboxylic acid 4-methoxybenzylamide 在 potassium tert-butylate 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 19.0h， 以92%的产率得到(1R,5S)-3,7-bis(4-methoxybenzyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-2-one
  参考文献：
  名称：

  A Flexible Route to Chiral 2-endo-Substituted 9-Oxabispidines and Their Application in the Enantioselective Oxidation of Secondary Alcohols

  摘要：

  A new and flexible route to enantiomerically pure bi- and tricyclic 9-oxabispidines has been developed with use of (1R,5S)-7-methyl-2-oxo-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester as the common late-stage intermediate. The 9-oxabispidines synthesized were evaluated as the chiral ligands in the Pd(II)-catalyzed oxidative kinetic resolution of secondary alcohols giving good to excellent selectivity factors of up to 19.

  DOI：

  10.1021/jo802409x

文献信息

• A Flexible Route to Chiral 2-<i>endo</i>-Substituted 9-Oxabispidines and Their Application in the Enantioselective Oxidation of Secondary Alcohols
  作者：Matthias Breuning、Melanie Steiner、Christian Mehler、Alexander Paasche、David Hein

  DOI：10.1021/jo802409x

  日期：2009.2.6

  A new and flexible route to enantiomerically pure bi- and tricyclic 9-oxabispidines has been developed with use of (1R,5S)-7-methyl-2-oxo-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester as the common late-stage intermediate. The 9-oxabispidines synthesized were evaluated as the chiral ligands in the Pd(II)-catalyzed oxidative kinetic resolution of secondary alcohols giving good to excellent selectivity factors of up to 19.