[(3S,8aS)-3-phenyl-8a-(trifluoromethyl)-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridin-5-yl] trifluoromethanesulfonate | 220453-09-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [(3S,8aS)-3-phenyl-8a-(trifluoromethyl)-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridin-5-yl] trifluoromethanesulfonate
• CAS: 220453-09-8
• 化学式: C₁₅H₁₃F₆NO₄S
• 分子量: 417.329
• InChiKey: XJPJSYFHDZMVRE-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  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 、 palladium dihydroxide copper(l) iodide 、 氢气 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 生成 (+)-trifluoromethyl monomorine
  参考文献：
  名称：

  Hydrogenation condition for sequential processes to (+)-trifluoromethyl monomorine

  摘要：

  Trifluoromethyl monomorine has been synthesized under mild hydrogenation condition by initiating reductive cleavage of the oxazoline ring followed by deprotection and intramolecular reductive amination reaction. The precursors could prepared concisely by condensation and palladium-catalyzed coupling reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.094
• 作为产物：
  描述：

  L-苯甘氨醇 在 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 生成 [(3S,8aS)-3-phenyl-8a-(trifluoromethyl)-2,3,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridin-5-yl] trifluoromethanesulfonate
  参考文献：
  名称：

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

  摘要：

  DOI：

  10.1021/ja983389n

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.