(1R,9R)-4-(2-Fluoro-phenyl)-10,10-dimethyl-3-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-triene | 349472-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1R,9R)-4-(2-Fluoro-phenyl)-10,10-dimethyl-3-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-triene
• CAS: 349472-86-2
• 化学式: C₁₈H₁₈FN
• 分子量: 267.346
• InChiKey: ZUFAJWKKFZSGLM-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  二苯基膦 、 (1R,9R)-4-(2-Fluoro-phenyl)-10,10-dimethyl-3-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-triene 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以49%的产率得到(6R,8R)-(+)-5,6,7,8-tetrahydro-7,7-dimethyl-2-(2-diphenylphosphinophenyl)-6,8-methanoquinoline
  参考文献：
  名称：

  Modular pyridine-type P , N -ligands derived from monoterpenes: application in asymmetric Heck addition

  摘要：

  Novel (diphenylphosphinophenyl)pyridine ligands (+)-8, (+)-15, (-)-21, and (-)-26 were synthesized from (-)-beta -pinene, (+)-3-carene, (+)-2-carene, and (-)-alpha -pinene, respectively, via Krohnke annulation as the key step, and shown to effect less than or equal to 88% ee in Heck addition (27 --> 28). Ligands (+)-15 and (-)-21 are quasi-enantiomeric; ligands 8 and 26 can be prepared in both enantiomeric forms from (+)- and (-)-enantiomers of alpha- and beta -pinene, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00369-0
• 作为产物：
  描述：

  2'-氟苯乙酮 在 ammonium acetate 、 碘 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 (1R,9R)-4-(2-Fluoro-phenyl)-10,10-dimethyl-3-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-triene
  参考文献：
  名称：

  Modular pyridine-type P , N -ligands derived from monoterpenes: application in asymmetric Heck addition

  摘要：

  Novel (diphenylphosphinophenyl)pyridine ligands (+)-8, (+)-15, (-)-21, and (-)-26 were synthesized from (-)-beta -pinene, (+)-3-carene, (+)-2-carene, and (-)-alpha -pinene, respectively, via Krohnke annulation as the key step, and shown to effect less than or equal to 88% ee in Heck addition (27 --> 28). Ligands (+)-15 and (-)-21 are quasi-enantiomeric; ligands 8 and 26 can be prepared in both enantiomeric forms from (+)- and (-)-enantiomers of alpha- and beta -pinene, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00369-0