(5R,6S)-3-(2-benzyloxy-5-(trifluorometoxy)phenyl)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]dec-3-ene | 200953-37-3

• 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: (5R,6S)-3-(2-benzyloxy-5-(trifluorometoxy)phenyl)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]dec-3-ene
• 英文别名: (5R)-3-[2-(Benzyloxy)-5-(trifluoromethoxy)phenyl]-6alpha-phenyl-1-oxa-7-azaspiro[4.5]deca-3-ene-7-carboxylic acid tert-butyl ester；tert-butyl (5R,10S)-10-phenyl-3-[2-phenylmethoxy-5-(trifluoromethoxy)phenyl]-1-oxa-9-azaspiro[4.5]dec-3-ene-9-carboxylate
• CAS: 200953-37-3
• 化学式: C₃₃H₃₄F₃NO₅
• 分子量: 581.632
• InChiKey: SLPGGRBWEPITLB-BHDXBOSCSA-N

物化性质

• 沸点：
  643.0±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (5R,6S)-3-(2-benzyloxy-5-(trifluorometoxy)phenyl)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]dec-3-ene 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 72.0h， 以70%的产率得到(3S,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：

  2-Bromo-4-(trifluoromethoxy)phenol 在 四(三苯基膦)钯 potassium carbonate 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 63.0h， 生成 (5R,6S)-3-(2-benzyloxy-5-(trifluorometoxy)phenyl)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]dec-3-ene
  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 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.