1-(2-endo-methyl-7-methyl-3,7-diazabicyclo[3.3.1]non-3-yl)-2-(S)-(6-methoxynaphthalen-2-yl)propan-1-one | 810692-25-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-endo-methyl-7-methyl-3,7-diazabicyclo[3.3.1]non-3-yl)-2-(S)-(6-methoxynaphthalen-2-yl)propan-1-one
• 英文别名: (2S)-1-[(1S,2R,5R)-2,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-3-yl]-2-(6-methoxynaphthalen-2-yl)propan-1-one
• CAS: 810692-25-2
• 化学式: C₂₃H₃₀N₂O₂
• 分子量: 366.503
• InChiKey: NIDZVROJAQCHSA-WCLQXYBISA-N

物化性质

• 沸点：
  534.9±50.0 °C(predicted)
• 密度：
  1.110±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-endo-methyl-7-methyl-3,7-diazabicyclo[3.3.1]non-3-yl)-2-(S)-(6-methoxynaphthalen-2-yl)propan-1-one 在 盐酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (+/-)-2-endo-methyl-3-carboxylic acid 7-methyl-3,7-diazabicyclo[3.3.1]nonane tert-butyl ester
  参考文献：
  名称：

  Is the A-Ring of Sparteine Essential for High Enantioselectivity in the Asymmetric Lithiation−Substitution of N-Boc-pyrrolidine?

  摘要：

  The simplest chiral portion of sparteine, N,N'-dimethyl-2-endo-methylbispidine, was prepared and evaluated in the asymmetric lithiation-substitution of N-Boc-pyrrolidine. The results indicate that the complete A-ring of sparteine is essential for high levels of asymmetric induction. DFT-QSSR analyses of the diamine/Li+ complexes and DFT calculations of the pertinent i-PrLi/diamine/N-Boc-pyrrolidine complexes are predictive and provide complementary pictures of the stereochemical features critical to this transformation.

  DOI：

  10.1021/ja046321i
• 作为产物：
  描述：

  3-苄基-7-甲基-3,7-二氮杂双环[3.3.1]-9-壬酮 在 palladium on activated charcoal 四甲基乙二胺 、 氢气 、 仲丁基锂 、 一水合肼 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 环戊烷 、 二乙二醇 为溶剂， 反应 42.0h， 生成 1-(2-endo-methyl-7-methyl-3,7-diazabicyclo[3.3.1]non-3-yl)-2-(S)-(6-methoxynaphthalen-2-yl)propan-1-one
  参考文献：
  名称：

  Is the A-Ring of Sparteine Essential for High Enantioselectivity in the Asymmetric Lithiation−Substitution of N-Boc-pyrrolidine?

  摘要：

  The simplest chiral portion of sparteine, N,N'-dimethyl-2-endo-methylbispidine, was prepared and evaluated in the asymmetric lithiation-substitution of N-Boc-pyrrolidine. The results indicate that the complete A-ring of sparteine is essential for high levels of asymmetric induction. DFT-QSSR analyses of the diamine/Li+ complexes and DFT calculations of the pertinent i-PrLi/diamine/N-Boc-pyrrolidine complexes are predictive and provide complementary pictures of the stereochemical features critical to this transformation.

  DOI：

  10.1021/ja046321i