| 946843-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 946843-09-0
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: MZPXPZHAOBAFAN-PVAVHDDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  61.55
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 六甲基磷酰三胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以40%的产率得到
  参考文献：
  名称：

  The first synthesis of N,O-protected β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers and their corresponding β-lactams

  摘要：

  The reaction of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic and mandelic acids, with (S-R,?)-tert-butyl sulfinyl ketimines, derived from butan-2-one, pentan-2-one, and decan-2-one, afforded conformation ally restrained beta(2,2,3,3) -isoserines bearing two adjacent quaternary stereogenic centers in the form of N-sulfinyl protected 1'-amino-dioxolan-4-ones. The selective acid-induced removal of the sulfinyl protecting group provided the corresponding 1'-aminodioxolanones, whose base-induced cyclization afforded the corresponding chiral tetra-substituted 3-hydroxy-beta-lactams. The synthesis of a dipeptide by reaction coupling between the 1'-aminodioxolanone (2S,5R,1'R)-19 and N,N-dimethylglycine was successfully achieved. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.087
• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 以88%的产率得到
  参考文献：
  名称：

  The first synthesis of N,O-protected β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers and their corresponding β-lactams

  摘要：

  The reaction of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic and mandelic acids, with (S-R,?)-tert-butyl sulfinyl ketimines, derived from butan-2-one, pentan-2-one, and decan-2-one, afforded conformation ally restrained beta(2,2,3,3) -isoserines bearing two adjacent quaternary stereogenic centers in the form of N-sulfinyl protected 1'-amino-dioxolan-4-ones. The selective acid-induced removal of the sulfinyl protecting group provided the corresponding 1'-aminodioxolanones, whose base-induced cyclization afforded the corresponding chiral tetra-substituted 3-hydroxy-beta-lactams. The synthesis of a dipeptide by reaction coupling between the 1'-aminodioxolanone (2S,5R,1'R)-19 and N,N-dimethylglycine was successfully achieved. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.087