(1R,2S,6R,7S)-1,10,10-trimethyl-4-pyridin-2-yl-3,5-diazatricyclo[5.2.1.02,6]dec-3-ene | 1169491-36-4

• 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: (1R,2S,6R,7S)-1,10,10-trimethyl-4-pyridin-2-yl-3,5-diazatricyclo[5.2.1.02,6]dec-3-ene
• CAS: 1169491-36-4
• 化学式: C₁₆H₂₁N₃
• 分子量: 255.363
• InChiKey: MLEQHEQCTBWUCU-VSBTWAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,6R,7S)-1,10,10-trimethyl-4-pyridin-2-yl-3,5-diazatricyclo[5.2.1.02,6]dec-3-ene 、 异丁酰氯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以89%的产率得到2-methyl-1-[(1S,2R,6S,7R)-7,10,10-trimethyl-4-pyridin-2-yl-3,5-diazatricyclo[5.2.1.02,6]dec-4-en-3-yl]propan-1-one
  参考文献：
  名称：

  在樟脑-咪唑啉配体催化的不对称亨利反应中探索电子和区域异构体的控制

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2009.04.010
• 作为产物：
  描述：

  2-氰基吡啶 在 sodium 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (1R,2S,6R,7S)-1,10,10-trimethyl-4-pyridin-2-yl-3,5-diazatricyclo[5.2.1.02,6]dec-3-ene
  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.