Carbamic acid,[(1S)-2-hydroxy-1-[[2-[(methylsulfonyl)oxy]ethoxy]methyl]-2,2-diphenylethyl]-, 1,1-dimethylethyl ester | 885321-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Carbamic acid,[(1S)-2-hydroxy-1-[[2-[(methylsulfonyl)oxy]ethoxy]methyl]-2,2-diphenylethyl]-, 1,1-dimethylethyl ester
• 英文别名: (S)-1-(2-tert-butoxycarbonylamino-3-hydroxy-3,3-diphenylpropoxy)-2-(methanesulfonyloxy)ethane
• CAS: 885321-49-3
• 化学式: C₂₃H₃₁NO₇S
• 分子量: 465.568
• InChiKey: HRPQIROBAYATTD-FQEVSTJZSA-N

物化性质

• 熔点：
  161 °C
• 沸点：
  666.6±55.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  111.16
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Carbamic acid,[(1S)-2-hydroxy-1-[[2-[(methylsulfonyl)oxy]ethoxy]methyl]-2,2-diphenylethyl]-, 1,1-dimethylethyl ester 在 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (S)-N-benzyl-3-(hydroxydiphenylmethyl)morpholine
  参考文献：
  名称：

  Synthesis of chiral C/N-functionalized morpholine alcohols: study of their catalytic ability as ligand in asymmetric diethylzinc addition to aldehyde

  摘要：

  A broad variety of chiral C/N-functionalized morpholine alcohols sharing a common structural motif in the 3-(hydroxy-methyl)morpholine 6 were prepared froin criantiomerically pure serine for the purpose of studying their catalytic ligand properties. The asymmetric addition of diethylzinc to benzaldehyde in the presence of 10 mol % of chiral C/N-functionalized morpholine alcohols gave 1-phenyl-1-propanol in 59-81% yield with 10-30% ee. The addition of 10 mol % of n-butyl lithium to the reaction mixture resulted in a significant enhancement of the stereoselectivity in the case of ligands bearing the two geminal phenyl substituents on the backbone. In the presence of n-butyl lithium and using (S)-3-(hydroxydiphcnylmethyl)morpholine (S)-19 as the chiral promoter, (S)-1-phenyl-1 -propanol was obtained in 81% yield with 76% ee. The geminal diphenyl-class of morpholine ligands was examined for the diethylzinc addition to four different aldehydes in the presence of n-butyl lithium. (S)-N-Benzyl-3-(hydroxydiphenymethyl)morpholine (S)-27 was found to be most enantioselective in the case of 4-metlioxybenzaldehyde to give (R)-alcohol in 87K yield with 80% ee. Catalysts (S)-19 and its N-methyl derivative (S)-26 gave alcohols with an (S)-absolute configuration while the N-benzylated derivative (S)-27 gave the opposite enantiomeric products. The tentative transition state models to account for the observed product stereoselectivity with morpholine ligands holding the geminal diphenyl group on the beta-amino alcohol segment are proposed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.027
• 作为产物：
  描述：

  Carbamic acid,[(1S)-2-hydroxy-1-[(2-hydroxyethoxy)methyl]-2,2-diphenylethyl]-,1,1-dimethylethyl ester 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到Carbamic acid,[(1S)-2-hydroxy-1-[[2-[(methylsulfonyl)oxy]ethoxy]methyl]-2,2-diphenylethyl]-, 1,1-dimethylethyl ester
  参考文献：
  名称：

  Synthesis of chiral C/N-functionalized morpholine alcohols: study of their catalytic ability as ligand in asymmetric diethylzinc addition to aldehyde

  摘要：

  A broad variety of chiral C/N-functionalized morpholine alcohols sharing a common structural motif in the 3-(hydroxy-methyl)morpholine 6 were prepared froin criantiomerically pure serine for the purpose of studying their catalytic ligand properties. The asymmetric addition of diethylzinc to benzaldehyde in the presence of 10 mol % of chiral C/N-functionalized morpholine alcohols gave 1-phenyl-1-propanol in 59-81% yield with 10-30% ee. The addition of 10 mol % of n-butyl lithium to the reaction mixture resulted in a significant enhancement of the stereoselectivity in the case of ligands bearing the two geminal phenyl substituents on the backbone. In the presence of n-butyl lithium and using (S)-3-(hydroxydiphcnylmethyl)morpholine (S)-19 as the chiral promoter, (S)-1-phenyl-1 -propanol was obtained in 81% yield with 76% ee. The geminal diphenyl-class of morpholine ligands was examined for the diethylzinc addition to four different aldehydes in the presence of n-butyl lithium. (S)-N-Benzyl-3-(hydroxydiphenymethyl)morpholine (S)-27 was found to be most enantioselective in the case of 4-metlioxybenzaldehyde to give (R)-alcohol in 87K yield with 80% ee. Catalysts (S)-19 and its N-methyl derivative (S)-26 gave alcohols with an (S)-absolute configuration while the N-benzylated derivative (S)-27 gave the opposite enantiomeric products. The tentative transition state models to account for the observed product stereoselectivity with morpholine ligands holding the geminal diphenyl group on the beta-amino alcohol segment are proposed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.027