4-Fluorocyclohexane-1-carboxylic acid | 174771-54-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 4-Fluorocyclohexane-1-carboxylic acid
• 英文别名: trans-4-fluorocyclohexanecarboxylic acid；4-fluorocyclohexane carboxylic acid
• CAS: 174771-54-1
• 化学式: C₇H₁₁FO₂
• 分子量: 146.162
• InChiKey: IUMDEBKXOXPBEX-IZLXSQMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2916209090
• 危险标志：
  GHS07
• 危险性描述：
  H302,H319
• 危险性防范说明：
  P280,P301 + P312 + P330,P305 + P351 + P338,P337 + P313

反应信息

• 作为反应物：
  描述：

  4-Fluorocyclohexane-1-carboxylic acid 在 1,1-二氯甲醚 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 trans-4-FCWAY
  参考文献：
  名称：

  Development of Fluorine-18-Labeled 5-HT_1A Antagonists

  摘要：

  We have synthesized five fluorinated derivatives of WAY 100635, N-{2-[4-(2-methoxyphenyl)piperazino]ethyl)-N-(2-pyridyl)cyclohexanecarboxamide (4a), using various acids in place of the cyclohexanecarboxylic acid (CHCA, 2a) in the reaction scheme. The five acids are 4-fluorobenzoic acid (FB, 2b), 4-fluoro-3-methylbenzoic acid (MeFB, 2c), trans-4-fluorocyclohexanecarboxylic acid (FC, 2d), 4-(fluoromethyl)benzoic acid (FMeB, 2e), and 3-nitro-4-(fluoromethyl)benzoic acid (NFMeB, 2f) (see Scheme 1). These compounds were radiolabeled with fluorine-18, and their biological properties were evaluated in rats and compared with those of [C-11]carbonyl WAY 100635 ([carbonyl-C-11]4a), [Carbonyl-C-11]4a cleared the brain with a biological half-life averaging 41 min. The metabolite-corrected blood radioactivity had a half-life of 29 min. [F-18]FCWAY ([F-18]4d) gave half-lives and intercepts comparable to [carbonyl-C-11]4a in the brain, but the blood clearance was faster. [F-18]FBWAY ([F-18]4b) showed an early rapid net efflux from the whole brain, clearing with a biological half-life of 35 min. The metabolite-corrected blood half-life was 41 min. The comparable whole brain and blood half-lives for Me[F-18]FBWAY ([F-18]4c) were 16 and 18 min, respectively. For each compound, the corresponding carboxylic acid was identified as a major metabolite in blood. Fluoride was also found after injection of [F-18]4d. However, for all compounds there was a good correlation (R > 0.97) between the differential uptake ratio (DUR, (%ID/g) x body weight (g)/100) in individual rat brain regions at 30 min after injection and the concentration of receptors as determined by in vitro quantitative autoradiography in rat. Specific binding ratios [region of interest (ROI)/ cerebellum-1] in control studies for cortex (Ctx) and hippocampus (H) were higher for [carbonyl-C-11]4a and [F-18]4d compared to [F-18]4b and [F-18]4c. [F-18]4d has similar pharmacokinetic properties and comparable specific binding ratios to [carbonyl-11C]4a. Fifty nanomoles of 4a blocked only 30% of the specific binding of [F-18]4d, while complete blockade was obtained from co-injection of 200 nmol of 4a (H/Cb-1 from 17.2 to 0.6). [F-18]4b and [F-18]4c showed lower specific binding ratios than [carbonyl-C-11]4a and [F-18]4d. [F-18]4c was superior to [F-18]4b since its specific binding was more readily blocked by 4a. These studies suggest that [F-18]4c should be a useful compound to assess dynamic changes in serotonin levels while [F-18]4d, with its high contrast and F-18 label, should provide better statistics and quantification for static measurement of 5-HT1A receptor distribution.

  DOI：

  10.1021/jm980456f
• 作为产物：
  描述：

  4-羟基环己烷甲酸乙酯 在 二乙胺基三氟化硫 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.03h， 生成 4-Fluorocyclohexane-1-carboxylic acid
  参考文献：
  名称：

  Development of Fluorine-18-Labeled 5-HT_1A Antagonists

  摘要：

  We have synthesized five fluorinated derivatives of WAY 100635, N-{2-[4-(2-methoxyphenyl)piperazino]ethyl)-N-(2-pyridyl)cyclohexanecarboxamide (4a), using various acids in place of the cyclohexanecarboxylic acid (CHCA, 2a) in the reaction scheme. The five acids are 4-fluorobenzoic acid (FB, 2b), 4-fluoro-3-methylbenzoic acid (MeFB, 2c), trans-4-fluorocyclohexanecarboxylic acid (FC, 2d), 4-(fluoromethyl)benzoic acid (FMeB, 2e), and 3-nitro-4-(fluoromethyl)benzoic acid (NFMeB, 2f) (see Scheme 1). These compounds were radiolabeled with fluorine-18, and their biological properties were evaluated in rats and compared with those of [C-11]carbonyl WAY 100635 ([carbonyl-C-11]4a), [Carbonyl-C-11]4a cleared the brain with a biological half-life averaging 41 min. The metabolite-corrected blood radioactivity had a half-life of 29 min. [F-18]FCWAY ([F-18]4d) gave half-lives and intercepts comparable to [carbonyl-C-11]4a in the brain, but the blood clearance was faster. [F-18]FBWAY ([F-18]4b) showed an early rapid net efflux from the whole brain, clearing with a biological half-life of 35 min. The metabolite-corrected blood half-life was 41 min. The comparable whole brain and blood half-lives for Me[F-18]FBWAY ([F-18]4c) were 16 and 18 min, respectively. For each compound, the corresponding carboxylic acid was identified as a major metabolite in blood. Fluoride was also found after injection of [F-18]4d. However, for all compounds there was a good correlation (R > 0.97) between the differential uptake ratio (DUR, (%ID/g) x body weight (g)/100) in individual rat brain regions at 30 min after injection and the concentration of receptors as determined by in vitro quantitative autoradiography in rat. Specific binding ratios [region of interest (ROI)/ cerebellum-1] in control studies for cortex (Ctx) and hippocampus (H) were higher for [carbonyl-C-11]4a and [F-18]4d compared to [F-18]4b and [F-18]4c. [F-18]4d has similar pharmacokinetic properties and comparable specific binding ratios to [carbonyl-11C]4a. Fifty nanomoles of 4a blocked only 30% of the specific binding of [F-18]4d, while complete blockade was obtained from co-injection of 200 nmol of 4a (H/Cb-1 from 17.2 to 0.6). [F-18]4b and [F-18]4c showed lower specific binding ratios than [carbonyl-C-11]4a and [F-18]4d. [F-18]4c was superior to [F-18]4b since its specific binding was more readily blocked by 4a. These studies suggest that [F-18]4c should be a useful compound to assess dynamic changes in serotonin levels while [F-18]4d, with its high contrast and F-18 label, should provide better statistics and quantification for static measurement of 5-HT1A receptor distribution.

  DOI：

  10.1021/jm980456f

文献信息

• Selective hydrogenation of fluorinated arenes using rhodium nanoparticles on molecularly modified silica
  作者：Souha Kacem、Meike Emondts、Alexis Bordet、Walter Leitner

  DOI：10.1039/d0cy01716g

  日期：——

  arenes using Rh nanoparticles on molecularly modified silica supports (Rh@Si–R) as highly effective and recyclable catalysts. The catalyst preparation comprises grafting non-polar molecular entities on the SiO2 surface generating a hydrophobic environment for controlled deposition of well-defined rhodium particles from a simple organometallic precursor. A broad range of fluorinated cyclohexane derivatives

  氟化环己烷衍生物的生产是通过在分子改性的二氧化硅载体（Rh @ Si–R）上作为高效且可回收的催化剂，使用Rh纳米粒子对易得的氟化芳烃进行选择性氢化来完成的。催化剂制备包括将非极性分子实体接枝在SiO 2表面上，从而产生疏水性环境，以控制从简单的有机金属前体中沉淀出明确的铑颗粒。各种氟化环己烷衍生物被证明具有出色的功效（0.05–0.5 mol％Rh，10–55 bar H 2，80–100°C，1-2小时），包括与工业相关的构建基块。添加CaO作为痕量HF的清除剂可大大提高催化体系的可回收性，并防止与HF存在相关的风险，而不会影响反应的活性和选择性。
• Generating rapamycin analogues by directed biosynthesis: starter acid substrate specificity of mono-substituted cyclohexane carboxylic acids
  作者：Rebecca J. M. Goss、Simon E. Lanceron、Nicola J. Wise、Steven J. Moss

  DOI：10.1039/b614519c

  日期：——

  We report a convenient synthesis of 4-fluorocyclohexanoic acid, and an insight into the rules governing acceptance of starter acid analogues in the precursor-directed biosynthesis of rapamycin.

  我们报道了4-氟环己酸的便捷合成，并深入探讨了在雷帕霉素的前体定向生物合成中接受起始酸类似物的规则。
• SPIROTROPANE COMPOUNDS
  申请人：Moinet Christophe

  公开号：US20110105546A1

  公开（公告）日：2011-05-05

  Compounds according to formula (I): wherein R 1 , R 2 , R 3 , n and X are defined as defined herein, and the pharmaceutically acceptable salts, hydrates and solvates thereof, are useful for the modulation of CCR5 chemokine receptor activity. Additionally, compounds according to Formula III: wherein Z, R′ 1 , and R′ 2 are defined as defined herein, and the pharmaceutically acceptable salts, hydrates and solvates thereof, are useful as intermediates for production of compounds that modulate CCR5 chemokine receptor activity.

  按照公式（I）定义的化合物：其中R1、R2、R3、n和X的定义如此处定义，并且其药学上可接受的盐、水合物和溶剂化物，可用于调节CCR5趋化因子受体活性。此外，按照公式（III）定义的化合物：其中Z、R'1和R'2的定义如此处定义，并且其药学上可接受的盐、水合物和溶剂化物，可用作调节CCR5趋化因子受体活性的化合物的生产中间体。
• Trifluoro-2-(trans-4-substituted cyclohexyl) ethylenes and process for their production
  申请人：ASAHI GLASS COMPANY LTD.

  公开号：EP0688752B1

  公开（公告）日：1999-01-13
• US5621147A
  申请人：——

  公开号：US5621147A

  公开（公告）日：1997-04-15