pseudoscopine | 498-46-4

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: pseudoscopine
• 英文别名: scopine；6exo,7exo-epoxy-tropane-3exo-ol; pseudoscopine；6exo,7exo-Epoxy-tropan-3exo-ol; Pseudoscopin；6exo,7exo-Epoxy-tropan-3exo-ol
• CAS: 498-46-4
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: FIMXSEMBHGTNKT-JWHZVDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.0
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  水 、 pseudoscopine 、 alkaline earth salt of/the/ methylsulfuric acid 生成 norpseudoscopine
  参考文献：
  名称：

  Polonovski; Polonovski, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1928, vol. 186, p. 148,149

  摘要：

  DOI：
• 作为产物：
  描述：

  1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene 在 palladium on activated charcoal 咪唑 、 sodium hydroxide 、 萘 、 甲烷磺酸 、 四丁基氟化铵 、 氢气 、 sodium 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， -78.0~80.0 ℃ 、101.33 kPa 条件下， 反应 164.58h， 生成 pseudoscopine
  参考文献：
  名称：

  Stereocontrolled epoxidations of cycloheptene derivatives in the palladium-catalyzed route to tropane alkaloids. Total syntheses of scopine and pseudoscopine

  摘要：

  Stereoselective total syntheses of the tropane alkaloids scopine (1) and pseudoscopine (3) have been developed via the chloroacetoxylation approach. Palladium-catalyzed 1,4-chloroacetoxylation of diene 6 afforded the key intermediate 7. Subsequent substitution of the allylic chloride by TsNH-with either retention (Pd(O) catalysis) or inversion (S(N)2) of configuration gave 10 and 16, respectively. The epoxy oxygen was introduced syn to the nitrogen function prior to cyclization by utilizing the syn-directive effect of the allylic sulfonamido group in the epoxidation. Cyclization of the epoxides 12 and 21, followed by replacement of the tosyl group by a methyl group and subsequent debenzylation, afforded the title compounds 1 and 3, respectively.

  DOI：

  10.1021/jo00008a037

文献信息

• [EN] FLUOROPHENYL SUBSTITUTED MUSCARINIC RECEPTOR LIGANDS WITH SELECTIVITY FOR M3 OVER M2<br/>[FR] LIGANDS DES RÉCEPTEURS MUSCARINIQUES À SUBSTITUTION FLUOROPHÉNYLE AYANT UNE SÉLECTIVITÉ POUR M3 SUR M2
  申请人：UNIV FRIEDRICH ALEXANDER ER

  公开号：WO2019110521A1

  公开（公告）日：2019-06-13

  The present invention relates to fluorophenyl substituted muscarinic receptor ligands with selectivity for M3 over M2 and to the use of these compounds in the treatment of various diseases such as asthma, chronic obstructive pulmonary disease (COPD), bronchopulmonary dysplasia (BPD) and urinary incontinence.

  本发明涉及氟苯基取代的毒蕈碱受体配体，其对M3受体的选择性高于M2受体，并涉及这些化合物在治疗哮喘、慢性阻塞性肺病（COPD）、支气管肺发育不良（BPD）和尿失禁等各种疾病中的用途。
• Exo- and endo-6-hydroxy- and 6,7-epoxytropanes; Total synthesis of scopine, pseudoscopine, and nor-derivatives
  作者：David E Justice、John R Malpass

  DOI：10.1016/0040-4039(95)00836-2

  日期：1995.6

  Novel endo- 6,7-epoxy-8-azabicyclo[3.2.1]octane derivatives and the corresponding exo-analogues have been synthesized and show substantially different reactivity; the resistance of the exo-epoxides to ring opening during hydride reduction and catalytic hydrogenolysis is exploited in a total synthesis of scopine, pseudoscopine, and nor -derivatives.

  已经合成了新型的内-6,7-环氧-8-氮杂双环[3.2.1]辛烷衍生物和相应的外-类似物，并显示出显着不同的反应性。在碱，假pseudo碱和正-衍生物的全合成中，利用了外环氧化合物在氢化物还原和催化氢解过程中对开环的抗性。
• Heusner; Zeile, Chemische Berichte, 1958, vol. 91, p. 2399,2403
  作者：Heusner、Zeile

  DOI：——

  日期：——
• Total synthesis of scopine, pseudoscopine, and nor- derivatives
  作者：David E. Justice、John R. Malpass

  DOI：10.1016/0040-4020(96)00693-x

  日期：1996.9

  Scopine and pseudoscopine have been synthesised from cyclohepta-3.5-dienol: the initial 1,4-fuctionalisation of the diene is based on a nitroso-cycloaddition. The use of the N-benzyloxycarbonyl group throughout the scheme allows ultimate reductive deprotection to yield N-methyl or novel NH (nor-) derivatives without damage to the exo-epoxide of the title compounds. Preliminary investigation of nitroso- cycloaddition to 5,6-epoxycyclohepta-1.3-diene is described. Copyright (C) 1996 Elsevier Science Ltd.
• Polonovski; Polonovski, Bulletin de la Societe Chimique de France, 1928, vol. <4> 43, p. 83
  作者：Polonovski、Polonovski

  DOI：——

  日期：——