N-{(1R,2S,3R,4S)-1,7,7-trimethyl-3-[(4-methylbenzenesulfonyl)amino]bicyclo[2.2.1]hept-2-yl}pyridine-2-carboxamide | 1169491-66-0

• 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: N-{(1R,2S,3R,4S)-1,7,7-trimethyl-3-[(4-methylbenzenesulfonyl)amino]bicyclo[2.2.1]hept-2-yl}pyridine-2-carboxamide
• 英文别名: N-[(1R,2S,3R,4S)-1,7,7-trimethyl-3-[(4-methylphenyl)sulfonylamino]-2-bicyclo[2.2.1]heptanyl]pyridine-2-carboxamide
• CAS: 1169491-66-0
• 化学式: C₂₃H₂₉N₃O₃S
• 分子量: 427.568
• InChiKey: CKQHLYIWYFJPIO-CFKGEZKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  96.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基吡啶亚胺甲酯 在 溶剂黄146 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.5h， 生成 (1S,2R,6S,7R)-7,10,10-trimethyl-5-(4-methylphenyl)sulfonyl-4-pyridin-2-yl-3,5-diazatricyclo[5.2.1.02,6]dec-3-ene 、 N-{(1R,2S,3R,4S)-1,7,7-trimethyl-3-[(4-methylbenzenesulfonyl)amino]bicyclo[2.2.1]hept-2-yl}pyridine-2-carboxamide
  参考文献：
  名称：

  Camphor-annelated imidazolines with various N1 and C2 pendants as tunable ligands for nitroaldol reactions

  摘要：

  Starting from (1R,2S,3R)-camphordiamine and (hetero)aromatic imidates and orthoformate, nine new camphor-annelated NH-imidazolines were synthesized. Subsequent N-modification was carried out via methylation, acylation, benzoylation, and sulfonylation. Two regioisomers were usually isolated with the ratios reflecting the structure of the starting NH-imidazoline and the electrophile used. All of the successfully prepared N1- and C2-substituted camphor-annelated imidazolines were applied to the asymmetric version of a Cu(II)-catalyzed Henry reaction. The electronic effects of both N1- and C2-pendants on the chemical and asymmetric outcomes of the nitroaldol reaction have been studied and discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.016

文献信息

• Probing electronic and regioisomeric control in an asymmetric Henry reaction catalyzed by camphor-imidazoline ligands
  作者：Filip Bureš、Jiří Kulhánek、Aleš Růžička

  DOI：10.1016/j.tetlet.2009.04.010

  日期：2009.6

  Starting from (R)-camphordiamine, 13 new camphor-annulated imidazoline ligands are synthesized in good yields as two regioisomeric series. Yields of up to 94% and good enantioselectivities up to 67% are achieved for the copper(II)-catalyzed Henry reaction giving the product stereoselectively according to the regioisomer used.

  从（R）-樟脑二胺开始，以两个区域异构体系列的高收率合成了13种新的樟脑环化的咪唑啉配体。对于铜（II）催化的亨利反应，根据所使用的区域异构体，立体选择性地产生产物，获得高达94％的产率和高达67％的良好对映选择性。
• Camphor-annelated imidazolines with various N1 and C2 pendants as tunable ligands for nitroaldol reactions
  作者：Jiří Tydlitát、Filip Bureš、Jiří Kulhánek、Grzegorz Mlostoń、Aleš Růžička

  DOI：10.1016/j.tetasy.2012.06.016

  日期：2012.7

  Starting from (1R,2S,3R)-camphordiamine and (hetero)aromatic imidates and orthoformate, nine new camphor-annelated NH-imidazolines were synthesized. Subsequent N-modification was carried out via methylation, acylation, benzoylation, and sulfonylation. Two regioisomers were usually isolated with the ratios reflecting the structure of the starting NH-imidazoline and the electrophile used. All of the successfully prepared N1- and C2-substituted camphor-annelated imidazolines were applied to the asymmetric version of a Cu(II)-catalyzed Henry reaction. The electronic effects of both N1- and C2-pendants on the chemical and asymmetric outcomes of the nitroaldol reaction have been studied and discussed. (C) 2012 Elsevier Ltd. All rights reserved.