9-formyl-9-hydroxyfluorene | 113388-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-formyl-9-hydroxyfluorene
• 英文别名: 9-hydroxy-9H-fluorene-9-carbaldehyde；9-hydroxyfluorene-9-carbaldehyde
• CAS: 113388-51-5
• 化学式: C₁₄H₁₀O₂
• 分子量: 210.232
• InChiKey: UCDNWFAVCKTEIG-UHFFFAOYSA-N

物化性质

• 熔点：
  104 °C(Solv: isopropanol (67-63-0))
• 沸点：
  415.5±45.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-formyl-9-hydroxyfluorene 在 盐酸羟胺 、 sodium carbonate 作用下， 以 industrial methylated spirit IMS 、 水 为溶剂， 生成 9-hydroxy-9H-fluorene-9-carbaldehyde oxime
  参考文献：
  名称：

  [EN] AZONIA BICYCLOALKANES AS M3 MUSCARINIC ACETYLCHOLIN RECEPTOR ANTAGONISTS
  [FR] AZONIA BICYCLOALCANES COMME ANTAGONISTES DU RÉCEPTEUR D'ACÉTYLCHOLINE MUSCARINIQUE M3

  摘要：

  该发明涉及以下式（I）的M3拮抗剂：其中R2、R4、R5、R6、W、V、A、D、X、t、u和v如本文所定义；含有它们的药物组合物；其制备方法；以及它们在治疗增强M3受体激活所涉及的疾病中的应用。

  公开号：

  WO2009098453A1
• 作为产物：
  描述：

  9-hydroxymethyl-9H-fluoren-9-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 9-formyl-9-hydroxyfluorene
  参考文献：
  名称：

  [EN] AZONIA BICYCLOALKANES AS M3 MUSCARINIC ACETYLCHOLIN RECEPTOR ANTAGONISTS
  [FR] AZONIA BICYCLOALCANES COMME ANTAGONISTES DU RÉCEPTEUR D'ACÉTYLCHOLINE MUSCARINIQUE M3

  摘要：

  该发明涉及以下式（I）的M3拮抗剂：其中R2、R4、R5、R6、W、V、A、D、X、t、u和v如本文所定义；含有它们的药物组合物；其制备方法；以及它们在治疗增强M3受体激活所涉及的疾病中的应用。

  公开号：

  WO2009098453A1

文献信息

• Reaction of α,β-unsaturated aldehydes with hydrogen peroxide catalysed by benzeneseleninic acids and their precursors
  作者：Ludwik Syper

  DOI：10.1016/s0040-4020(01)86890-3

  日期：1987.1

  Oxidation of α,β-unsaturated aldehydes with hydrogen peroxide catalysed by benzeneseleninic acids and their precursors has been investigated. Bis 2-nitrophenyl diselenide has proved to be the most effective catalyst. The major products resulting from the oxidation are vinyl formates (a) which on hydrolysis give saturated aldehydes or ketones (g) having the carbon chain shortened by one carbon atom

  研究了苯硒酸及其前体催化的过氧化氢对α，β-不饱和醛的氧化作用。已证明双2-硝基苯基二硒化物是最有效的催化剂。氧化产生的主要产物是乙烯基甲酸酯（a），与起始的醛相比，乙烯基甲酸酯（a）在水解时得到饱和的醛或酮（g），其碳链缩短了一个碳原子。次要产物是甲氧基氧肟酮（b），α-羟基羰基（e）和α-甲氧基羰基（f）化合物，其碳链缩短了一个碳原子。也已经分离出正式衍生自碳-碳双键的氧化裂变的羰基化合物d。当肉桂醛（4）或1-苯基-2-甲酰氧基丙烷（5a）分别被氧化时，已分离出二甲酰氧基（4c）和甲酰氧基乙酰氧基苯基甲烷（5c）。讨论了这些产物形成的可能机理。当α，β-不饱和醛被有机过氧酸氧化时，得到类似的产物。
• Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-Unsaturated Lactones
  作者：Masahiro Egi、Yuya Ota、Yuka Nishimura、Kaori Shimizu、Kenji Azechi、Shuji Akai

  DOI：10.1021/ol401824v

  日期：2013.8.16

  AgOTf-catalyzed intramolecular cyclization of phenoxyethynyl diols proceeded under mild conditions to afford the multisubstituted alpha,beta-unsaturated-gamma-lactones in 55-98% yields. This method was also applicable to the synthesis of alpha,beta-unsaturated-delta-lactones. A similar cyclization proceeded when AgOTf was replaced with a stoichiometric amount of N-bromosuccinimide to furnish the a-bromo-substituted alpha,beta-unsaturated lactones.
• Effect of oxime substituents on 9-fluorenyl carbocations
  作者：Xavier Creary、Allison Wolf

  DOI：10.1002/1099-1395(200006)13:6<337::aid-poc249>3.0.co;2-t

  日期：2000.6

  9-Fluorenyl carbocations substituted with the oxime functional groups CH=NOCH3, CH3C=NOCH3, and i-PrC=NOCH3 were generated by solvolyses of the corresponding chlorides in methanol, These cations form at rates which greatly exceed those of formation of the parent 9-fluorenyl cation. Relative rate data suggest that stabilization of 9-fluorenyl cations by CH=NOCH3 is greater than stabilization by CH3C=NOCH3, which is in turn greater than that by i-PrC=NOCH3. Computational studies on these cations show that the oxime group is progressively rotated out of conjugation with the cationic center as the oxime group becomes larger. These rate and computational studies also suggest that 9-fluorenyl cations are not antiaromatic. They are essentially delocalized 'nonatetraenyl' cations, where formally antiaromatic resonance forms contribute little to the overall structure. Copyright (C) 2000 John Wiley & Sons, Ltd.
• SYPER, LUDWIK, TETRAHEDRON, 43,(1987) N 12, 2853-2871
  作者：SYPER, LUDWIK

  DOI：——

  日期：——
• [EN] AZONIA BICYCLOALKANES AS M3 MUSCARINIC ACETYLCHOLIN RECEPTOR ANTAGONISTS<br/>[FR] AZONIA BICYCLOALCANES COMME ANTAGONISTES DU RÉCEPTEUR D'ACÉTYLCHOLINE MUSCARINIQUE M3
  申请人：ASTRAZENECA AB

  公开号：WO2009098453A1

  公开（公告）日：2009-08-13

  This invention relates to M3 antagonists of formula (I): wherein R2, R4, R5, R6, W, V, A, D, X, t, u and v are as defined herein; pharmaceutical compositions containing them; methods for their preparation; and their use in the treatment of diseases where enhanced M3 receptor activation is implicated.

  该发明涉及以下式（I）的M3拮抗剂：其中R2、R4、R5、R6、W、V、A、D、X、t、u和v如本文所定义；含有它们的药物组合物；其制备方法；以及它们在治疗增强M3受体激活所涉及的疾病中的应用。