(4S,5S)-1,3-bis(2-(naphthalen-2-yl)phenyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate | 1256752-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S,5S)-1,3-bis(2-(naphthalen-2-yl)phenyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate
• 英文别名: (4S,5S)-1,3-bis(2-(naphthalen-2-yl)phenyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate salt；(4S,5S)-1,3-bis(2-naphthalen-2-ylphenyl)-4,5-diphenyl-4,5-dihydroimidazol-1-ium;tetrafluoroborate
• CAS: 1256752-93-8
• 化学式: BF₄*C₄₇H₃₅N₂
• 分子量: 714.613
• InChiKey: LDMVHJBHVKPRRK-NAFLKVCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  54
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(2-溴苯基)萘 在 ammonium tetrafluoroborate 、 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (4S,5S)-1,3-bis(2-(naphthalen-2-yl)phenyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate
  参考文献：
  名称：

  SmI₂-Mediated Radical Cyclizations Directed by a C−Si Bond

  摘要：

  The use of a silicon stereocontrol element in cyclobutanol and cyclopentanol-forming cyclizations mediated by SmI2 results in excellent diastereocontrol. The C-Si bond in the products of cyclization provides a versatile handle for further manipulation. An asymmetric route to cyclization substrates involving copper-catalyzed silyl transfer has also been developed.

  DOI：

  10.1021/ol102278c
• 作为试剂：
  描述：

  (2E)-3-[3-(三氟甲基)苯基]丙烯酰氯 、 N-甲基对甲苯磺酰胺 在 copper(l) iodide 、 正丁基锂 、 (4S,5S)-1,3-bis(2-(naphthalen-2-yl)phenyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 正己烷 为溶剂， 反应 18.5h， 生成 (R)-3-(dimethyl(phenyl)silyl)-N-methyl-N-tosyl-3-(3-(trifluoromethyl)phenyl)propanamide 、 (S)-3-(dimethyl(phenyl)silyl)-N-methyl-N-tosyl-3-(3-(trifluoromethyl)phenyl)propanamide
  参考文献：
  名称：

  Cu(I)–NHC Catalyzed Asymmetric Silyl Transfer to Unsaturated Lactams and Amides

  摘要：

  The first asymmetric silylation of unsaturated lactams and amides using Cu(I)-NHC catalysts and PhMe(2)SiBpin has been accomplished. The method has been exploited in an expedient asymmetric synthesis of the (R)-enantiomer of the nootropic drug oxiracetam.

  DOI：

  10.1021/ol4033623

文献信息

• SmI₂-Mediated Radical Cyclizations Directed by a C−Si Bond
  作者：Hassan Y. Harb、Karl D. Collins、Jose V. Garcia Altur、Sue Bowker、Leonie Campbell、David J. Procter

  DOI：10.1021/ol102278c

  日期：2010.12.3

  The use of a silicon stereocontrol element in cyclobutanol and cyclopentanol-forming cyclizations mediated by SmI2 results in excellent diastereocontrol. The C-Si bond in the products of cyclization provides a versatile handle for further manipulation. An asymmetric route to cyclization substrates involving copper-catalyzed silyl transfer has also been developed.