(1R,2S)-2-(benzyl(methyl)amino)-1,2-diphenylethanol | 156592-83-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1R,2S)-2-(benzyl(methyl)amino)-1,2-diphenylethanol
• 英文别名: (1R,2S)-2-[benzyl(methyl)amino]-1,2-diphenylethanol
• CAS: 156592-83-5
• 化学式: C₂₂H₂₃NO
• 分子量: 317.431
• InChiKey: XKGVODLIURNSDV-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二苯基氯化膦 、 (1R,2S)-2-(benzyl(methyl)amino)-1,2-diphenylethanol 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以84%的产率得到(1S,2R)-N-benzyl-2-diphenylphosphanyloxy-N-methyl-1,2-diphenylethanamine
  参考文献：
  名称：

  Easily accessible chiral amino-phosphinite ligands for highly enantioselective palladium-mediated allylic alkylation

  摘要：

  Palladium-catalyzed asymmetric allylic alkylation of 1,3-diplienyl-2-propenyl acetate with the dimethyl malonate-BSA-LiOAc system has been successfully carried out in the presence of easily prepared new chiral amino-phosphinite ligands such as 3b and 3c to result in good yields and excellent enantioselectivities of up to 95%, e.e. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00204-5
• 作为产物：
  描述：

  (1R,2S)-2-氨基-1,2-二苯基乙醇 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 12.5h， 生成 (1R,2S)-2-(benzyl(methyl)amino)-1,2-diphenylethanol
  参考文献：
  名称：

  Easily accessible chiral amino-phosphinite ligands for highly enantioselective palladium-mediated allylic alkylation

  摘要：

  Palladium-catalyzed asymmetric allylic alkylation of 1,3-diplienyl-2-propenyl acetate with the dimethyl malonate-BSA-LiOAc system has been successfully carried out in the presence of easily prepared new chiral amino-phosphinite ligands such as 3b and 3c to result in good yields and excellent enantioselectivities of up to 95%, e.e. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00204-5
• 作为试剂：
  描述：

  Dimethylzinc 、 N-(3-methoxy-benzylidene)-P,P-diphenylphosphonamide 在 (1R,2S)-2-(benzyl(methyl)amino)-1,2-diphenylethanol 作用下， 以 hexanes 、 甲苯 为溶剂， 反应 48.0h， 生成 (R)-N-(1-(3-methoxyphenyl)ethyl)-P,P-diphenylphosphinic amide
  参考文献：
  名称：

  Aromatic motifs in the design of Ephedra ligands for application in the asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines

  摘要：

  Using N-benzylephedrine as a model, a collection of N-arylmethylephedrine derivatives has been prepared. These derivatives were prepared by treatment of ephedrine with selected aldehydes to create oxazolidines 8a-e. Reduction of the oxazolidines with lithium aluminum hydride afforded the target beta-amino alcohols 9a-e. When applied in the catalytic asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines, the derivatives yielded product enantioselectivities that were comparable to those of N-benzylephedrine. An N-cyclohexylmethylephedrine derivative was also prepared: this 13-aminoalcohol did not perform well in the catalytic addition of diethylzinc to 2-naphthaldehyde, thus suggesting that the aromatic motif is important in terms of maintaining a reasonable level of asymmetric induction. Finally, N-benzyl-N-methyl-2-amino-1,2-diphenyl-1-ethanol, an analogue of the N-benzylephedrine derivative, was prepared. This compound yielded comparable enantioselectivities in the catalytic asymmetric addition when employed as a ligand. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.026

文献信息

• Easily accessible chiral amino-phosphinite ligands for highly enantioselective palladium-mediated allylic alkylation
  作者：Guoshu Chen、Xin Li、Haile Zhang、Liuzhu Gong、Aiqiao Mi、Xin Cui、Yaozhong Jiang、Michael C.K. Choi、Albert S.C. Chan

  DOI：10.1016/s0957-4166(02)00204-5

  日期：2002.5

  Palladium-catalyzed asymmetric allylic alkylation of 1,3-diplienyl-2-propenyl acetate with the dimethyl malonate-BSA-LiOAc system has been successfully carried out in the presence of easily prepared new chiral amino-phosphinite ligands such as 3b and 3c to result in good yields and excellent enantioselectivities of up to 95%, e.e. (C) 2002 Published by Elsevier Science Ltd.
• Aromatic motifs in the design of Ephedra ligands for application in the asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines
  作者：Sucharita Banerjee、Anthony J. Camodeca、Gregory G. Griffin、Christopher G. Hamaker、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2010.02.026

  日期：2010.3

  Using N-benzylephedrine as a model, a collection of N-arylmethylephedrine derivatives has been prepared. These derivatives were prepared by treatment of ephedrine with selected aldehydes to create oxazolidines 8a-e. Reduction of the oxazolidines with lithium aluminum hydride afforded the target beta-amino alcohols 9a-e. When applied in the catalytic asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines, the derivatives yielded product enantioselectivities that were comparable to those of N-benzylephedrine. An N-cyclohexylmethylephedrine derivative was also prepared: this 13-aminoalcohol did not perform well in the catalytic addition of diethylzinc to 2-naphthaldehyde, thus suggesting that the aromatic motif is important in terms of maintaining a reasonable level of asymmetric induction. Finally, N-benzyl-N-methyl-2-amino-1,2-diphenyl-1-ethanol, an analogue of the N-benzylephedrine derivative, was prepared. This compound yielded comparable enantioselectivities in the catalytic asymmetric addition when employed as a ligand. (C) 2010 Elsevier Ltd. All rights reserved.