4-hydroxy-N-methoxy-N-methylnonanamide | 1360562-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-N-methoxy-N-methylnonanamide
• CAS: 1360562-60-2
• 化学式: C₁₁H₂₃NO₃
• 分子量: 217.309
• InChiKey: MYJUEPVHDBTGAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-N-methoxy-N-methylnonanamide 在 titanium(IV) tetraethanolate 、 lithium aluminium tetrahydride 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 43.17h， 生成 (Ss,5S,2E)-(+)-methyl N-(tert-butylsulfinyl)-5-amino-7-(2-pentyl-1,3-dioxolan-2-yl)-hept-2-enoate
  参考文献：
  名称：

  Enantioselective Synthesis of Cocaine C-1 Analogues using Sulfinimines (N-Sulfinyl Imines)

  摘要：

  The first examples of cocaine analogues having substituents (methyl, ethyl, n-propyl, n-pentyl, and phenyl) at the C-1 position of the cocaine tropane skeleton were prepared by heating sulfinimine-derived alpha,beta-unsaturated pyrrolidine nitrones. In the presence of the Lewis acid Al((OBu)-Bu-t)(3) the nitrones undergo an intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines that were transformed in three steps to the cocaine analogues. In the absence of the Lewis acid, lactams were formed resulting from rearrangement of the nitrone to an oxaziridine. A novel Pd-and base-promoted rearrangement of methanesulfonate salts of isoxazolidine to bridge bicyclic[4.2.1]isoxazolidines was discovered.

  DOI：

  10.1021/jo202652f
• 作为产物：
  描述：

  二甲羟胺盐酸盐 、 γ-壬内酯 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 4-hydroxy-N-methoxy-N-methylnonanamide
  参考文献：
  名称：

  Enantioselective Synthesis of Cocaine C-1 Analogues using Sulfinimines (N-Sulfinyl Imines)

  摘要：

  The first examples of cocaine analogues having substituents (methyl, ethyl, n-propyl, n-pentyl, and phenyl) at the C-1 position of the cocaine tropane skeleton were prepared by heating sulfinimine-derived alpha,beta-unsaturated pyrrolidine nitrones. In the presence of the Lewis acid Al((OBu)-Bu-t)(3) the nitrones undergo an intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines that were transformed in three steps to the cocaine analogues. In the absence of the Lewis acid, lactams were formed resulting from rearrangement of the nitrone to an oxaziridine. A novel Pd-and base-promoted rearrangement of methanesulfonate salts of isoxazolidine to bridge bicyclic[4.2.1]isoxazolidines was discovered.

  DOI：

  10.1021/jo202652f