2-phenyl-2-cyclohexene-1-carbonyl chloride | 145450-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-phenyl-2-cyclohexene-1-carbonyl chloride
• 英文别名: 2-phenylcyclohex-2-enecarboxylic chloride；2-Phenylcyclohex-2-enecarboxylic chloride；2-phenylcyclohex-2-ene-1-carbonyl chloride
• CAS: 145450-39-1
• 化学式: C₁₃H₁₃ClO
• 分子量: 220.699
• InChiKey: YUAGCXNHVFHMOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenyl-2-cyclohexene-1-carbonyl chloride 在 三乙胺 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  N-alkyl-nor-tropine esters of 2-phenyl-cyclohexenic acids as new bronchodilator agents. Effect of structural and conformational modifications on affinity for muscarinic receptors

  摘要：

  A series of N-alkyl-nor-tropine esters of 2-phenyl-2-cyclohexene-1-carboxylic, 2-phenyl-cyclohexanecarboxylic, and 2-phenyl-1-cyclohexene-1-acetic acids and their quaternary ammonium salts were synthesized and evaluated for bronchodilator activity by binding assays and pharmacological tests. The in vitro and in vivo functional activity results showed that some quaternary derivatives are potent anticholinergic bronchodilator agents, and 4 compounds (14-A, 16-A, 25-A and 28-A) were selected for pharmacotoxicological evaluation. The binding data also indicated that the affinity of these compounds for the tracheal membrane muscarinic receptors is markedly affected by structural modifications of both the cationic head and the acyl moiety of the molecule. In the series of N-alkyl-nor-tropine 2-phenyl-2-cyclohexene-1-carboxylate derivatives, a rather strict limitation of the bulk of the equatorial substituent of tropine nitrogen is required for very high affinity. Conformational analysis and molecular graphics techniques evidenced an influence of the acyl moiety conformation on the affinity of the different tropinic esters, suggesting that the carbonyl oxygen may participate in interaction with the binding site, eliciting a marked increase of potency when it is oriented in a proper conformation with respect to the tropinic nitrogen and the phenyl ring.

  DOI：

  10.1016/0223-5234(92)90179-5
• 作为产物：
  描述：

  2-(羟基甲基)环己酮 在 potassium permanganate 、 氯化亚砜 、 硫酸 、 溶剂黄146 作用下， 反应 0.25h， 生成 2-phenyl-2-cyclohexene-1-carbonyl chloride
  参考文献：
  名称：

  摘要：

  Purpose. To design and evaluate a new class of soft anticholinergics with subtype selectivity.Methods. A new class of soft anticholinergics was designed based on the "inactive metabolite" approach. Four compounds were synthesized. The potency and soft nature of the compounds were evaluated by receptor binding, cardiac, and mydriatic studies. Stability and pharmacokinetic studies were also performed on these newly synthesized soft anticholinergics.Results. Receptor binding studies of the soft anticholinergics on cloned muscarinic receptors indicated pKi values in the range of 7.5 to 8.9. Two compounds, 9a and 13a, of the series showed muscarinic subtype receptor selectivity (M-3/M-2). In mydriatic studies, 13a and 13b showed shorter duration of action in the treated eyes than tropicamide. In the control eyes, significant dilation of pupils was found only in rabbits treated with atropine and tropicamide, indicating that the soft anticholinergics lack systemic effects because of their facile hydrolytic deactivation. Consistent with their soft nature, this new class of soft anticholinergics displayed much shorter cardiovascular effects in the carbachol-induced bradycardia (10 to 15 min) in rats than atropine (>60 min). Stability and pharmacokinetic studies suggested that the new soft anticholinergics were rapidly eliminated from plasma (systemic circulation) after i.v. administration.Conclusions. A new class of anticholinergics was designed and synthesized, and the PK/PD evaluation confirmed they were potent "soft" anticholinergics; two of them showed muscarinic receptor subtype selectivity (M-3/M-2).

  DOI：

  10.1023/a:1026160023030

文献信息

• Esters of N-alkyl-nortropines and their quaternary derivatives having anti-bronchospastic activity, process for their preparation and pharmaceutical compositions containing them
  申请人：Laboratori Guidotti S.p.A.

  公开号：EP0234400A1

  公开（公告）日：1987-09-02

  The esters of N-alkyl-nortropines with phenyl-cyclohexen-carboxylic and phenyl-cyclohexen-acetic acids and their quaternary ammonium derivatives with alkyl halides and alkyl sulphates having general formula: wherein when and when whereas R'= -, -H, -CH3, -CH2-CH3, -CH2-CH2-CH3, -CH(CH3)2, -CH2-CH2-CH2-CH3, -CH2-CH-(CH3)2 X- = Cl, Br, J, CH3S04 show anti-bronchospastic activity. The invention relates also to the processes for their preparation and to the pharmaceutical compositions containing them.

  N-烷基去甲托品与苯基-环己烯-羧酸和苯基-环己烯-乙酸的酯及其与烷基卤化物和烷基硫酸盐的季铵盐衍生物，其通式为 其中 当 和 而 R'= -、-H、-CH3、-CH2- 、- - - 、-CH( )2、- - - - 、- -CH-( )2 X- = Cl、Br、J、 S04 显示抗支气管痉挛活性。 本发明还涉及它们的制备工艺和含有它们的药物组合物。
• US4780467A
  申请人：——

  公开号：US4780467A

  公开（公告）日：1988-10-25