3-[(3S,5S,8aS)-3-phenyl-8a-(trifluoromethyl)-2,3,5,6,7,8-hexahydro-[1,3]oxazolo[3,2-a]pyridin-5-yl]propan-1-ol | 220453-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-[(3S,5S,8aS)-3-phenyl-8a-(trifluoromethyl)-2,3,5,6,7,8-hexahydro-[1,3]oxazolo[3,2-a]pyridin-5-yl]propan-1-ol
• CAS: 220453-22-5
• 化学式: C₁₇H₂₂F₃NO₂
• 分子量: 329.362
• InChiKey: PCLLQGRXIJOXRW-XHSDSOJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[(3S,5S,8aS)-3-phenyl-8a-(trifluoromethyl)-2,3,5,6,7,8-hexahydro-[1,3]oxazolo[3,2-a]pyridin-5-yl]propan-1-ol 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 以86%的产率得到3-[(2S,6R)-6-(trifluoromethyl)piperidin-2-yl]propan-1-ol
  参考文献：
  名称：

  Asymmetric Synthesis of Chiral, Nonracemic Trifluoromethyl-Substituted Piperidines and Decahydroquinolines

  摘要：

  DOI：

  10.1021/ja983389n
• 作为产物：
  描述：

  [(3S,8aS)-3-phenyl-8a-(trifluoromethyl)-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridin-5-yl] trifluoromethanesulfonate 在 platinum(IV) oxide bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 30.0h， 生成 3-[(3S,5S,8aS)-3-phenyl-8a-(trifluoromethyl)-2,3,5,6,7,8-hexahydro-[1,3]oxazolo[3,2-a]pyridin-5-yl]propan-1-ol
  参考文献：
  名称：

  Syntheses and structure–activity relationship studies of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists

  摘要：

  Syntheses and structure-activity relationships of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists are described. Some of substituents on the piperidine ring that were investigated included a fused phenyl group, a (6R)-trifluoromethyl group, (6S) and (6R)-methyl group. This study showed that GnRH binding potency was tolerated by a small group at the 6-position of the piperidine, and blocking the 6-position by a trifluoromethyl group reduced clearance rate and increased oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.101

文献信息

• Syntheses and structure–activity relationship studies of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists
  作者：Jinlong Jiang、Robert J. DeVita、Mark T. Goulet、Matthew J. Wyvratt、Jane-L. Lo、Ning Ren、Joel B. Yudkovitz、Jisong Cui、Yi T. Yang、Kang Cheng、Susan P. Rohrer

  DOI：10.1016/j.bmcl.2003.12.101

  日期：2004.4

  Syntheses and structure-activity relationships of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists are described. Some of substituents on the piperidine ring that were investigated included a fused phenyl group, a (6R)-trifluoromethyl group, (6S) and (6R)-methyl group. This study showed that GnRH binding potency was tolerated by a small group at the 6-position of the piperidine, and blocking the 6-position by a trifluoromethyl group reduced clearance rate and increased oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of Chiral, Nonracemic Trifluoromethyl-Substituted Piperidines and Decahydroquinolines
  作者：Jinlong Jiang、Robert J. DeVita、George A. Doss、Mark T. Goulet、Matthew J. Wyvratt

  DOI：10.1021/ja983389n

  日期：1999.1.1