(3R,5S,6S)-3-(2-benzyloxy-5-(trifluoromethoxy)phenyl)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]decane | 200954-98-9

• 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: (3R,5S,6S)-3-(2-benzyloxy-5-(trifluoromethoxy)phenyl)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]decane
• 英文别名: (3R,5R,6S)-3-(2-Benzyloxy-5-(trifluoromethoxy)phenyl)-7-(tert-butoxycarbonyl)-6-phenyl-7-aza-1-oxa-spiro[4.5]decane；tert-butyl (3R,5R,10S)-10-phenyl-3-[2-phenylmethoxy-5-(trifluoromethoxy)phenyl]-1-oxa-9-azaspiro[4.5]decane-9-carboxylate
• CAS: 200954-98-9
• 化学式: C₃₃H₃₆F₃NO₅
• 分子量: 583.648
• InChiKey: ODQLMZCEDQBLRO-XTGFQOFXSA-N

物化性质

• 沸点：
  630.9±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,5S,6S)-3-(2-benzyloxy-5-(trifluoromethoxy)phenyl)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]decane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以99%的产率得到(3R,5R,6S)-3-(2-hydroxy-5-(trifluoromethoxy)phenyl)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]decane
  参考文献：
  名称：

  Stereocontrolled Syntheses of Epimeric 3-Aryl-6-phenyl-1-oxa-7-azaspiro[4.5]decane NK-1 Receptor Antagonist Precursors

  摘要：

  [GRAPHICS]Complementary stereoselective syntheses of individual C3 epimers of the NK-1 receptor antagonist precursor 1 have been developed. Both diastereomers were derived from the common intermediate 3; introduction of the 3S stereocenter in 1a was achieved through hydrogenation of an arylated dihydrofuran, whereas the corresponding stereogenic center in 1b was installed using a stereo- and regioselective alkene hydroarylation.

  DOI：

  10.1021/ol006944a
• 作为产物：
  描述：

  1-哌啶羧酸,3-羰基-2-苯基-,1,1-二甲基乙基酯,(2S)- 在 Lindlar's catalyst 、 lithium chloride palladium diacetate 、 四丁基氟化铵 、 四丁基氯化铵 、 氢气 、 potassium formate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 46.0h， 生成 (3R,5S,6S)-3-(2-benzyloxy-5-(trifluoromethoxy)phenyl)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]decane
  参考文献：
  名称：

  Stereocontrolled Syntheses of Epimeric 3-Aryl-6-phenyl-1-oxa-7-azaspiro[4.5]decane NK-1 Receptor Antagonist Precursors

  摘要：

  [GRAPHICS]Complementary stereoselective syntheses of individual C3 epimers of the NK-1 receptor antagonist precursor 1 have been developed. Both diastereomers were derived from the common intermediate 3; introduction of the 3S stereocenter in 1a was achieved through hydrogenation of an arylated dihydrofuran, whereas the corresponding stereogenic center in 1b was installed using a stereo- and regioselective alkene hydroarylation.

  DOI：

  10.1021/ol006944a

文献信息

• Spiro-azacyclic derivatives, their preparation and their use as
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US06046195A1

  公开（公告）日：2000-04-04

  The present invention relates to certain spiro-azacyclic derivatives which are tachykinin antagonists and are useful, for example, in the treatment or prevention of pain, inflammation, migraine, emesis and postherpetic neuralgia.

  本发明涉及某些螺环氮杂环衍生物，其是速激肽拮抗剂，并且可用于治疗或预防疼痛、炎症、偏头痛、恶心和带状疱疹后神经痛等症状。
• SPIRO-AZACYCLIC DERIVATIVES, THEIR PREPARATION AND THEIR USE AS TACHYKININ ANTAGONISTS
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0929554B1

  公开（公告）日：2006-03-15
• US6046195A
  申请人：——

  公开号：US6046195A

  公开（公告）日：2000-04-04
• Stereocontrolled Syntheses of Epimeric 3-Aryl-6-phenyl-1-oxa-7-azaspiro[4.5]decane NK-1 Receptor Antagonist Precursors
  作者：Janusz J. Kulagowski、Neil R. Curtis、Christopher J. Swain、Brian J. Williams

  DOI：10.1021/ol006944a

  日期：2001.3.1

  [GRAPHICS]Complementary stereoselective syntheses of individual C3 epimers of the NK-1 receptor antagonist precursor 1 have been developed. Both diastereomers were derived from the common intermediate 3; introduction of the 3S stereocenter in 1a was achieved through hydrogenation of an arylated dihydrofuran, whereas the corresponding stereogenic center in 1b was installed using a stereo- and regioselective alkene hydroarylation.