tert-Butyl-((2R,3S)-2-methoxy-2,3-dimethyl-tetrahydro-furan-3-yl)-amine | 1932101-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-((2R,3S)-2-methoxy-2,3-dimethyl-tetrahydro-furan-3-yl)-amine
• 英文别名: 3-Furanamine, N-(1,1-dimethylethyl)tetrahydro-2-methoxy-2,3-dimethyl-, (2R,3S)-；(2R,3S)-N-tert-butyl-2-methoxy-2,3-dimethyloxolan-3-amine
• CAS: 1932101-04-6
• 化学式: C₁₁H₂₃NO₂
• 分子量: 201.309
• InChiKey: NHYDHQCBZOKCMA-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(3-Chloro-2-butylidene)t-butylamine 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 22.5h， 生成 tert-Butyl-((2R,3S)-2-methoxy-2,3-dimethyl-tetrahydro-furan-3-yl)-amine
  参考文献：
  名称：

  Stereospecific Synthesis of cis-2-Alkoxy-3-aminooxolanes

  摘要：

  cis-2-Alkoxy-3-aminooxolanes 4 were synthesized in a remarkably stereospecific manner by alcoholysis of alpha-chloro-gamma-((trimethylsilyl)oxy)ketimines 2, obtained by alkylation of alpha-chloroketimines 1 with 2-bromo-1-((trimethylsilyl)oxy)ethane. The stereospecificity of the cyclization was lost when the alcoholysis was performed in the presence of base. However, complete transformation of the mixtures of cis- and trans-2-alkoxy-3-aminooxolanes into the more stable cis-compounds was achieved with hydrogen chloride in methanol. A mechanistic rationale for these stereochemical aspects is presented.

  DOI：

  10.1021/jo970410e

文献信息

• Stereospecific Synthesis of <i>cis</i>-2-Alkoxy-3-aminooxolanes
  作者：Norbert De Kimpe、Wim Aelterman、Koen De Geyter、Jean-Paul Declercq

  DOI：10.1021/jo970410e

  日期：1997.7.1

  cis-2-Alkoxy-3-aminooxolanes 4 were synthesized in a remarkably stereospecific manner by alcoholysis of alpha-chloro-gamma-((trimethylsilyl)oxy)ketimines 2, obtained by alkylation of alpha-chloroketimines 1 with 2-bromo-1-((trimethylsilyl)oxy)ethane. The stereospecificity of the cyclization was lost when the alcoholysis was performed in the presence of base. However, complete transformation of the mixtures of cis- and trans-2-alkoxy-3-aminooxolanes into the more stable cis-compounds was achieved with hydrogen chloride in methanol. A mechanistic rationale for these stereochemical aspects is presented.