[S(S)]-N-[(1R)-1-(3-exo)-8-[2-(4-morpholinylsulfonyl)acetyl]-8-azabicyclo[3.2.1]oct-3-yl-2-(2,4,5-frifluorophenyl)ethyl]-2-methyl-2-propanesulfinamide | 1073923-27-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [S(S)]-N-[(1R)-1-(3-exo)-8-[2-(4-morpholinylsulfonyl)acetyl]-8-azabicyclo[3.2.1]oct-3-yl-2-(2,4,5-frifluorophenyl)ethyl]-2-methyl-2-propanesulfinamide
• CAS: 1073923-27-9
• 化学式: C₂₅H₃₆F₃N₃O₅S₂
• 分子量: 579.705
• InChiKey: LUGBULKNPKATEK-JUZPMFBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  96.02
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [S(S)]-N-[(1R)-1-(3-exo)-8-[2-(4-morpholinylsulfonyl)acetyl]-8-azabicyclo[3.2.1]oct-3-yl-2-(2,4,5-frifluorophenyl)ethyl]-2-methyl-2-propanesulfinamide 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以72%的产率得到1-{3-[(R)-1-amino-2-(2,4,5-frifluorophenyl)ethyl]-8-azabicyclo[3.2.1]oct-8-yl}-2-(morpholine-4-sulfonyl)ethanone
  参考文献：
  名称：

  A Scalable Synthesis of an Azabicyclooctanyl Derivative, a Novel DPP-4 Inhibitor

  摘要：

  A practical synthetic strategy to a chiral azabicycclooctanyl derivative (1), a potent DPP-4 inhibitor, starting from a commercially available nortropine is described. The stereogenic center of 1 was established employing a modified protocol of Ellman's diastereoselective addition of a benzylic nucleophile to tert-butanesulfinimme. Other key steps include Corey-Chaykovsky reaction, Meinwald rearrangement, and CDMT-promoted amide bond formation involving a sterically hindered amine 2.

  DOI：

  10.1021/jo801830x
• 作为产物：
  描述：

  [S(S)]-N-[(1R)-1-(3-exo)-8-azabicyclo[3.2.1]oct-3-yl-2-(2,4,5-frifluorophenyl)ethyl]-2-methyl-2-propanesulfinamide 、 (吗啉-4-磺酰基)-乙酸 在 N-甲基吗啉 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以99%的产率得到[S(S)]-N-[(1R)-1-(3-exo)-8-[2-(4-morpholinylsulfonyl)acetyl]-8-azabicyclo[3.2.1]oct-3-yl-2-(2,4,5-frifluorophenyl)ethyl]-2-methyl-2-propanesulfinamide
  参考文献：
  名称：

  A Scalable Synthesis of an Azabicyclooctanyl Derivative, a Novel DPP-4 Inhibitor

  摘要：

  A practical synthetic strategy to a chiral azabicycclooctanyl derivative (1), a potent DPP-4 inhibitor, starting from a commercially available nortropine is described. The stereogenic center of 1 was established employing a modified protocol of Ellman's diastereoselective addition of a benzylic nucleophile to tert-butanesulfinimme. Other key steps include Corey-Chaykovsky reaction, Meinwald rearrangement, and CDMT-promoted amide bond formation involving a sterically hindered amine 2.

  DOI：

  10.1021/jo801830x

文献信息

• ORGANIC COMPOUNDS
  申请人：Baeschlin Daniel Kaspar

  公开号：US20090281069A1

  公开（公告）日：2009-11-12

  The present invention relates to compounds of the formula; and their use in therapy.

  本发明涉及公式化合物及其在治疗中的应用。
• US7888351B2
  申请人：——

  公开号：US7888351B2

  公开（公告）日：2011-02-15