(5R,6S)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]dec-3-ene | 200956-77-0

• 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)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]dec-3-ene
• 英文别名: (5R,S-6S)-6-Phenyl-1-oxa-7-aza-spiro[4.5]dec-3-ene-7-carboxylic acid tert-butyl ester；(5R,6S)-6-phenyl-1-oxa-7-(tert-butyloxycarbonyl)-7-azaspiro[4.5]dec-3-ene；(5R,6S)-7-(tert-Butoxycarbonyl)-6-phenyl-7-aza-1-oxa-spiro[4.5]dec-3-ene；tert-butyl (5R,10S)-10-phenyl-1-oxa-9-azaspiro[4.5]dec-3-ene-9-carboxylate
• CAS: 200956-77-0
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: ADWIVEYTJVKKNJ-QFBILLFUSA-N

物化性质

• 沸点：
  426.6±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,6S)-6-phenyl-1-oxa-7-(tert-butoxycarbonyl)azaspiro[4.5]dec-3-ene 在 palladium on activated charcoal 、 lithium chloride palladium diacetate 、 四丁基氯化铵 、 氢气 、 potassium formate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、344.75 kPa 条件下， 反应 53.0h， 生成 (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 四丁基氟化铵 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 (5R,6S)-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

• Benzoamide piperidine containing compounds and related compounds
  申请人：——

  公开号：US20030087925A1

  公开（公告）日：2003-05-08

  The present invention relates to certain benzoamide piperidine containing compounds and related compounds that exhibit activity as NK-1 receptor antagonists, (e.g., substance P receptor antagonists), to pharmaceutical compositions containing them, and to their use in the treatment and prevention of central nervous system disorders, inflammatory disorders, cardiovascular disorders, ophthalmic disorders, gastrointestinal disorders, disorders caused by helicobacter pylori, disorders of the immune system, urinary incontinence, pain, migraine, emesis, angiogenesis and other disorders.

  本发明涉及某些含有苯甲酰胺哌啶类化合物和相关化合物，这些化合物表现出作为NK-1受体拮抗剂（例如，物质P受体拮抗剂）的活性，以及含有它们的药物组合物，以及它们在治疗和预防中枢神经系统疾病、炎症性疾病、心血管疾病、眼科疾病、消化系统疾病、幽门螺杆菌引起的疾病、免疫系统疾病、尿失禁、疼痛、偏头痛、呕吐、血管生成和其他疾病的治疗中的用途。
• Spiro-azacyclic derivatives and their use as therapeutic agents
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US06225320B1

  公开（公告）日：2001-05-01

  Substituted spiro-azacyclic derivatives of structural formula I are tachykinin receptor antagonists of use, for example, in the treatment of pain, inflammation, migraine, emesis and posttherpetic neuralgia Wherein A is a pyridyl, X is —CH2—, Y is —CH2— or —CH═ and q is 2.

  结构式I的取代螺环氮杂环衍生物是一种速激肽受体拮抗剂，可用于治疗疼痛、炎症、偏头痛、呕吐和带状疱疹后神经痛。其中A是吡啶基，X是—CH2—，Y是—CH2—或—CH═，q为2。
• Carbon-14 labeling of a trifluoromethoxy group: synthesis of a substance P antagonist
  作者：Conrad E. Raab、Dennis C. Dean、David G. Melillo

  DOI：10.1002/jlcr.502

  日期：2001.10.30

  Synthesis of a carbon-14 labeled trifluoromethoxy group has been accomplished using the stepwise oxidative fluorination–desulfurization of a readily prepared [14C]xanthate (5). This novel labeling procedure allowed a rapid synthesis of substance P antagonist candidate 1 that avoided potentially more complex ring-labeling procedures. Similar procedures have been used to prepare C-14 labeled trifluoromethyl and trifluoromethylamine groups. Copyright © 2001 John Wiley & Sons, Ltd.

  通过对容易制备的[14C]黄原酸盐（5）进行逐步氧化氟化-脱硫，合成了碳-14 标记的三氟甲氧基。这种新颖的标记程序可以快速合成候选的 P 物质拮抗剂 1，避免了可能更为复杂的环标记程序。类似的程序也被用于制备 C-14 标记的三氟甲基和三氟甲胺基团。Copyright © 2001 John Wiley & Sons, Ltd. All Rights Reserved.
• 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