(S)-2-((R)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)ethylamino)-3-methylbutan-1-ol | 1426434-48-1

• 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: (S)-2-((R)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)ethylamino)-3-methylbutan-1-ol
• 英文别名: (2S)-2-[[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-(3,4-dimethoxyphenyl)ethyl]amino]-3-methylbutan-1-ol
• CAS: 1426434-48-1
• 化学式: C₂₁H₃₉NO₄Si
• 分子量: 397.63
• InChiKey: VKMJEOGHHLCNRI-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-((R)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)ethylamino)-3-methylbutan-1-ol 在 三氟化硼乙醚 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 diborane
  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
• 作为产物：
  描述：

  (S)-methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)ethylamino)-3-methylbutanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以77%的产率得到(S)-2-((R)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)ethylamino)-3-methylbutan-1-ol
  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.