2-phenylcyclohex-2-ene-1-carboxylic acid | 24102-01-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 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-phenylcyclohex-2-ene-1-carboxylic acid
• 英文别名: 2-phenylcyclohex-2-enecarboxylic acid；2-Phenyl-cyclohexen-3-carbonsaeure；2-Phenylcyclohex-2-en-carbonsaeure；2-Phenyl-2-cyclohexencarbonsaeure
• CAS: 24102-01-0
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: FPXFKRJXSSAIMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  76-80 °C(Solv: ligroine (8032-32-4))
• 沸点：
  364.6±42.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenylcyclohex-2-ene-1-carboxylic acid 在 氯化亚砜 作用下， 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
• 作为产物：
  描述：

  2-(羟基甲基)环己酮 在 potassium permanganate 、 硫酸 、 溶剂黄146 作用下， 反应 0.25h， 生成 2-phenylcyclohex-2-ene-1-carboxylic acid
  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

• EtAlCl₂/2,6-Disubstituted Pyridine-Mediated Carboxylation of Alkenes with Carbon Dioxide
  作者：Shinya Tanaka、Kota Watanabe、Yuuki Tanaka、Tetsutaro Hattori

  DOI：10.1021/acs.orglett.6b00918

  日期：2016.6.3

  and trialkyl-substituted alkenes undergo carboxylation with CO2 in the presence of EtAlCl2 and 2,6-dibromopyridine to afford the corresponding α,β- and/or β,γ-unsaturated carboxylic acids. This reaction is suggested to proceed via the electrophilic substitution of EtAlCl2 with the aid of the base, followed by the carbonation of the resulting ate complex. This reaction can be applied to terminal dialkylalkenes

  在EtAlCl 2和2,6-二溴吡啶的存在下，α-芳基烯烃和三烷基取代的烯烃与CO 2进行羧化反应，得到相应的α，β-和/或β，γ-不饱和羧酸。建议该反应通过在碱的辅助下对EtAlCl 2进行亲电取代，然后将所得的盐配合物碳酸化来进行。通过使用2，6-二叔丁基吡啶和2，6-二溴吡啶的混合物，该反应可用于末端二烷基烯烃。
• [EN] METHODS FOR MAKING CYCLOHEXENE OXIDE-CONTAINING ESTERS<br/>[FR] PROCÉDÉS DE FABRICATION D'ESTERS CONTENANT DE L'OXYDE DE CYCLOHEXÈNE
  申请人：ARKEMA INC

  公开号：WO2018231804A1

  公开（公告）日：2018-12-20

  A method of making an ester comprised of at least one cyclohexene oxide moiety is provided, involving the steps of a) esterifying an alcohol with a carboxylic acid-substituted cyclohexene to obtain an intermediate comprised of at least one carboxylate-substituted cyclohexene moiety; and b) epoxidizing the intermediate obtained in step a) with an epoxidizing agent to obtain the ester comprised of at least one cyclohexene oxide moiety. The esters have utility as acid scavengers, plasticizers and reactive resins.

  提供一种制备至少含有一个环己烯氧化物基团的酯的方法，包括以下步骤：a)用具有羧基取代环己烯的羧酸酯化醇，以获得至少含有一个羧酸酯基团的环己烯中间体；b)用环氧化剂环氧化步骤a)中获得的中间体，以获得至少含有一个环己烯氧化物基团的酯。这些酯具有作为酸中和剂、增塑剂和反应性树脂的用途。
• 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-CH3、-CH2-CH2-CH3、-CH(CH3)2、-CH2-CH2-CH2-CH3、-CH2-CH-(CH3)2 X- = Cl、Br、J、CH3S04 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。
• Catalytic photocarboxylation of 1,1-diphenylethylene with N,N,N′,N′-tetramethylbenzidine and carbon dioxide
  作者：Yoshikatsu Ito

  DOI：10.1016/j.tet.2007.02.013

  日期：2007.4

  Photocarboxylation of 1,1 -diphenylethylene with N,N,N',N',-tetramethylbenzidine (TMB) in MeCN under bubbling Of CO2 proceeded with high catalytic efficiency, giving 3,3-diphenylacrylic acid (DPA) and 3-hydroxy-3,3-diphenylpropionic acid (20). The turnover number (TON=(DPA+20)/TMB) reached 17. Similarly, 1-phenyl-1-cyclohexene yielded cis-2-acetamido-2-phenylcyclohexanecarboxylic acid with TON 5.9. As compared with related N,N-dimethylaniline derivatives, TMB is more resistant to photodecomposition, has the much larger absorbance in the S-0 -> S-1 transition, and has the lower quenching efficiency by CO2. Probably these factors are partly responsible for the high TON observed for TMB. (c) 2007 Elsevier Ltd. All rights reserved.
• METHODS FOR MAKING CYCLOHEXENE OXIDE-CONTAINING ESTERS
  申请人：Arkema Inc.

  公开号：US20200165218A1

  公开（公告）日：2020-05-28

  A method of making an ester comprised of at least one cyclohexene oxide moiety is provided, involving the steps of a) esterifying an alcohol with a carboxylic acid-substituted cyclohexene to obtain an intermediate comprised of at least one carboxylate-substituted cyclohexene moiety; and b) epoxidizing the intermediate obtained in step a) with an epoxidizing agent to obtain the ester comprised of at least one cyclohexene oxide moiety. The esters have utility as acid scavengers, plasticizers and reactive resins.