((S)-2-Dibutylcarbamoyl-1-methyl-ethyl)-carbamic acid tert-butyl ester | 851849-15-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ((S)-2-Dibutylcarbamoyl-1-methyl-ethyl)-carbamic acid tert-butyl ester
• CAS: 851849-15-5
• 化学式: C₁₇H₃₄N₂O₃
• 分子量: 314.469
• InChiKey: VDMJSMVZDWEAKJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ((S)-2-Dibutylcarbamoyl-1-methyl-ethyl)-carbamic acid tert-butyl ester 在 对甲苯磺酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 1.0h， 生成 (2R,3S)-3-Amino-N,N-dibutyl-2-methyl-butyramide
  参考文献：
  名称：

  Reversible Enolization of β-Amino Carboxamides by Lithium Hexamethyldisilazide

  摘要：

  The enolization of beta-amino carboxamides by lithium hexamethyldisilazide (LiHMDS) in THF/ toluene and subsequent diastereoselective alkylation with CH3I are reported. In situ IR spectroscopic studies reveal that P-amino carboxamides coordinate to LiHMDS at -78 degrees C before enolization. Comparison with structurally similar carboxamides suggests that the P-amino group promotes the enolization. I R spectroscopic studies also show that the enolization is reversible. Efficient trapping of the enolate by CH3I affords full conversion to products. Li-6 and N-15 NMR spectroscopic studies reveal that lithium enolate-LiHMDS mixed dimers and trimers as well as a homoaggregated enolate are formed during the reaction. At ambient temperature, racemization of the beta-position through a putative reversible Michael addition was observed.

  DOI：

  10.1021/ja043470s
• 作为产物：
  描述：

  在 silver benzoate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 ((S)-2-Dibutylcarbamoyl-1-methyl-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Reversible Enolization of β-Amino Carboxamides by Lithium Hexamethyldisilazide

  摘要：

  The enolization of beta-amino carboxamides by lithium hexamethyldisilazide (LiHMDS) in THF/ toluene and subsequent diastereoselective alkylation with CH3I are reported. In situ IR spectroscopic studies reveal that P-amino carboxamides coordinate to LiHMDS at -78 degrees C before enolization. Comparison with structurally similar carboxamides suggests that the P-amino group promotes the enolization. I R spectroscopic studies also show that the enolization is reversible. Efficient trapping of the enolate by CH3I affords full conversion to products. Li-6 and N-15 NMR spectroscopic studies reveal that lithium enolate-LiHMDS mixed dimers and trimers as well as a homoaggregated enolate are formed during the reaction. At ambient temperature, racemization of the beta-position through a putative reversible Michael addition was observed.

  DOI：

  10.1021/ja043470s