2-((1R,3S,4S)-1-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-3-isopropyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)acetonitrile | 1426434-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-((1R,3S,4S)-1-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-3-isopropyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)acetonitrile
• 英文别名: 2-[(1R,3S,4S)-1-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxy-6,7-dimethoxy-3-propan-2-yl-3,4-dihydro-1H-isoquinolin-2-yl]acetonitrile
• CAS: 1426434-50-5
• 化学式: C₂₃H₃₈N₂O₄Si
• 分子量: 434.651
• InChiKey: XLDDZIAYKNQLSI-NYVOZVTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  75
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-methyl 2-((R)-1-(3,4-dimethoxyphenyl)-2-hydroxyethylamino)-3-methylbutanoate 在 咪唑 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 戴斯-马丁氧化剂 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 2,2,2-三氟乙醇 、 甲苯 为溶剂， 反应 10.5h， 生成 2-((1R,3S,4S)-1-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-3-isopropyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)acetonitrile
  参考文献：
  名称：

  An Approach to the Synthesis of Enantiopure Tetrahydroisoquinoline via a Key Asymmetric Ugi Reaction

  摘要：

  An approach to the synthesis of the multisubstituted tetrahydroisoquinoline featuring an asymmetric Ugi reaction of a-amino acid, aromatic aldehyde and an isocyanide has been developed. The promising utility of the strategy is demonstrated by a synthesis of an enantiopure functionalized 1,3-trans-tetrahydroiso-quinolin-4-ol from natural L-valine. The configuration of the two stereocenters at C-1 and C-4, generated in the Ugi reaction and Pomeranz-Fritsch-type cyclization separately, was controlled very well and determined by NMR studies.

  DOI：

  10.1055/s-0032-1317931

文献信息

• An Approach to the Synthesis of Enantiopure Tetrahydroisoquinoline via a Key Asymmetric Ugi Reaction
  作者：Xiaochuan Chen、Li Pan、Ruijiao Chen、Dongshun Ni、Liang Xia

  DOI：10.1055/s-0032-1317931

  日期：——

  An approach to the synthesis of the multisubstituted tetrahydroisoquinoline featuring an asymmetric Ugi reaction of a-amino acid, aromatic aldehyde and an isocyanide has been developed. The promising utility of the strategy is demonstrated by a synthesis of an enantiopure functionalized 1,3-trans-tetrahydroiso-quinolin-4-ol from natural L-valine. The configuration of the two stereocenters at C-1 and C-4, generated in the Ugi reaction and Pomeranz-Fritsch-type cyclization separately, was controlled very well and determined by NMR studies.