tert-Butyl 5-Methyl-3-aminohexanoate, 1 Naphthamide | 138878-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-Butyl 5-Methyl-3-aminohexanoate, 1 Naphthamide
• 英文别名: tert-butyl (3R)-5-methyl-3-(naphthalene-1-carbonylamino)hexanoate
• CAS: 138878-09-8
• 化学式: C₂₂H₂₉NO₃
• 分子量: 355.477
• InChiKey: HPKXYBYYGDFWEM-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-(3,5-Dihydro-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-5-methyl-hexanoic acid tert-butyl ester 在 palladium dihydroxide 4-二甲氨基吡啶 、 morpholinium formate 、 三乙胺 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 14.7h， 生成 tert-Butyl 5-Methyl-3-aminohexanoate, 1 Naphthamide
  参考文献：
  名称：

  An asymmetric ammonia synthon for Michael additions

  摘要：

  The highly diastereoselective 1,4-addition of lithiated chiral amine 1 to alpha,beta-unsaturated esters, followed by hydrogenolysis of the benzylic-type C-N bonds of the 1,4-adducts, provides an asymmetric ammonia synthon for Michael additions. Under optimized conditions, lithiated 1 adds to alpha,beta-unsaturated tert-butyl esters in dimethoxyethane at -63-degrees-C in high yield with very high diastereoselectivity. Small, large, functionalized, and chiral beta-ester substituents are amenable, with (S)-1 consistently adding to (E)-3 from the top as drawn in Table II. Hydrogenolysis liberates the beta-amino esters with typically 95-99% ee.

  DOI：

  10.1021/jo00033a037