(3aR,8bS)-2-(2-fluorophenyl)-4,4-dimethyl-4,8b-dihydro-3aH-indeno[2,1-d]oxazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3aR,8bS)-2-(2-fluorophenyl)-4,4-dimethyl-4,8b-dihydro-3aH-indeno[2,1-d]oxazole
• 英文别名: (3aR,8bS)-2-(2-fluorophenyl)-4,4-dimethyl-3a,8b-dihydroindeno[2,1-d][1,3]oxazole
• 化学式: C₁₈H₁₆FNO
• 分子量: 281.33
• InChiKey: IGWINOXIDREIHB-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium diphenylphosphine 、 (3aR,8bS)-2-(2-fluorophenyl)-4,4-dimethyl-4,8b-dihydro-3aH-indeno[2,1-d]oxazole 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 1.0h， 以29%的产率得到(3AR,8bS)-2-(2-(diphenylphosphanyl)phenyl)-4,4-dimethyl-3a,8b-dihydro-4H-indeno[2,1-d]oxazole
  参考文献：
  名称：

  A Widely Applicable Chiral Auxiliary, cis-2-Amino-3,3-dimethyl-1-indanol:  Conversion to a Novel Phosphorus-Containing Oxazoline and Its Application as a Highly Efficient Ligand for the Palladium-Catalyzed Enantioselective Allylic Amination Reaction

  摘要：

  A chiral amino alcohol, cis-2-amino-3,3-dimethyl-1-indanol (2), was converted into the corresponding enantiomerically pure phosphorus-containing oxazoline 4. Oxazoline 4 was found to be an efficient ligand for palladium-catalyzed enantioselective allylic amination reactions: In the amination reaction of (E)-1,3-diphenyl-2-propen-1-yl acetate (7a), 4 was found to be more efficient than the similar ligands 1a-c, derived from valinol, tert-leucinol, etc. Other 1,3-bis(p-substituted aryl)-2-propen-1-yl acetates were also converted to the corresponding amines in a similar manner and with excellent enantioselectivity. In the amination reaction of 1-alkyl-3,3-diphenyl-2-propen-1-yl acetates 11, the correponding amines 12 were obtained with excellent enantioselectivity when acetic acid was added to the reaction system.

  DOI：

  10.1021/jo970359e
• 作为产物：
  描述：

  2-氟苯腈 、 (1S,2R)-2-amino-3,3-dimethyl-2,3-dihydro-1H-inden-1-ol 在 zinc(II) chloride 作用下， 以 氯苯 为溶剂， 反应 48.0h， 以30%的产率得到(3aR,8bS)-2-(2-fluorophenyl)-4,4-dimethyl-4,8b-dihydro-3aH-indeno[2,1-d]oxazole
  参考文献：
  名称：

  A Widely Applicable Chiral Auxiliary, cis-2-Amino-3,3-dimethyl-1-indanol:  Conversion to a Novel Phosphorus-Containing Oxazoline and Its Application as a Highly Efficient Ligand for the Palladium-Catalyzed Enantioselective Allylic Amination Reaction

  摘要：

  A chiral amino alcohol, cis-2-amino-3,3-dimethyl-1-indanol (2), was converted into the corresponding enantiomerically pure phosphorus-containing oxazoline 4. Oxazoline 4 was found to be an efficient ligand for palladium-catalyzed enantioselective allylic amination reactions: In the amination reaction of (E)-1,3-diphenyl-2-propen-1-yl acetate (7a), 4 was found to be more efficient than the similar ligands 1a-c, derived from valinol, tert-leucinol, etc. Other 1,3-bis(p-substituted aryl)-2-propen-1-yl acetates were also converted to the corresponding amines in a similar manner and with excellent enantioselectivity. In the amination reaction of 1-alkyl-3,3-diphenyl-2-propen-1-yl acetates 11, the correponding amines 12 were obtained with excellent enantioselectivity when acetic acid was added to the reaction system.

  DOI：

  10.1021/jo970359e

文献信息

• Highly Efficient Synthesis of (Phosphinodihydrooxazole)- (1,5-cyclooctadiene) Iridium Complexes
  作者：Volodymyr Semeniuchenko、Volodymyr Khilya、Ulrich Groth

  DOI：10.1515/znb-2009-1007

  日期：2009.10.1

  A highly efficient one-pot procedure for the synthesis of complexes of the type [Ir(COD)(Phox)]X, where Phox is a (chiral) phosphinooxazoline ligand, X = PF₆ or B[(3,5-(CF₃)₂C₆H₃)]₄ (BARF), is developed. Former reported syntheses demanded the isolation of pure ligands by column chromatography, but the ligands tend to adsorb irreversibly on silica. Moreover, the chromatography has to be performed with careful exclusion of air. The present method avoids this difficulties. The yields of the syntheses are comparable with those starting from the pure ligands. The method is also suitable for the preparation of complexes of the type [Rh(COD)(Phox)]BARF and [Rh(Phox)₂]BARF.

  一种高效的一锅法合成方法用于合成类型为[Ir(COD)(Phox)]X的配合物，其中Phox是一种(手性)膦氧杂环丙酮配体，X = PF₆或B[(3,5-(CF₃)₂C₆H₃)]₄（BARF）。先前报道的合成方法要求通过柱层析分离纯配体，但配体往往会在硅胶上不可逆地吸附。此外，层析过程必须小心排除空气。目前的方法避免了这些困难。合成的产率与从纯配体开始的产率相当。该方法还适用于合成类型为[Rh(COD)(Phox)]BARF和[Rh(Phox)₂]BARF的配合物。
• A Widely Applicable Chiral Auxiliary, <i>cis</i>-2-Amino-3,3-dimethyl-1-indanol:  Conversion to a Novel Phosphorus-Containing Oxazoline and Its Application as a Highly Efficient Ligand for the Palladium-Catalyzed Enantioselective Allylic Amination Reaction
  作者：Atsushi Sudo、Kazuhiko Saigo

  DOI：10.1021/jo970359e

  日期：1997.8.1

  A chiral amino alcohol, cis-2-amino-3,3-dimethyl-1-indanol (2), was converted into the corresponding enantiomerically pure phosphorus-containing oxazoline 4. Oxazoline 4 was found to be an efficient ligand for palladium-catalyzed enantioselective allylic amination reactions: In the amination reaction of (E)-1,3-diphenyl-2-propen-1-yl acetate (7a), 4 was found to be more efficient than the similar ligands 1a-c, derived from valinol, tert-leucinol, etc. Other 1,3-bis(p-substituted aryl)-2-propen-1-yl acetates were also converted to the corresponding amines in a similar manner and with excellent enantioselectivity. In the amination reaction of 1-alkyl-3,3-diphenyl-2-propen-1-yl acetates 11, the correponding amines 12 were obtained with excellent enantioselectivity when acetic acid was added to the reaction system.