4-(4-fluorophenyl)-4-hydroxycyclohexanone | 36716-69-5

• 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: 4-(4-fluorophenyl)-4-hydroxycyclohexanone
• 英文别名: 4-(p-Fluorphenyl)-4-hydroxycyclohexanon；4-(4-fluorophenyl)-4-hydroxy-1-cyclohexanone；4-(4-Fluorophenyl)-4-hydroxycyclohexan-1-one
• CAS: 36716-69-5
• 化学式: C₁₂H₁₃FO₂
• 分子量: 208.232
• InChiKey: JFJXHTCDSDMHPT-UHFFFAOYSA-N

物化性质

• 沸点：
  345.0±42.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-4-hydroxycyclohexanone 生成 1-(4-氟-苯基)-4-环己酮
  参考文献：
  名称：

  联苯部分还原为中枢神经系统制剂。2.顺式和反式4-芳基环己胺。

  摘要：

  DOI：

  10.1021/jm00282a009
• 作为产物：
  描述：

  8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以79%的产率得到4-(4-fluorophenyl)-4-hydroxycyclohexanone
  参考文献：
  名称：

  [EN] TRIAZOLOPYRIDINE ETHER DERIVATIVES AND THEIR USE IN NEUROLOGICAL AND PYSCHIATRIC DISORDERS
  [FR] DÉRIVÉS D'ÉTHER DE TRIAZOLOPYRIDINE ET LEUR UTILISATION CONTRE DES TROUBLES NEUROLOGIQUES ET PYSCHIATRIQUES

  摘要：

  该披露通常涉及到I式化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物调节mGluR2受体，可能有助于治疗中枢神经系统的各种疾病。

  公开号：

  WO2015042243A1

文献信息

• 4-AZETIDINYL-1-PHENYL-CYCLOHEXANE ANTAGONISTS OF CCR2
  申请人：Zhang Xuqing

  公开号：US20100267689A1

  公开（公告）日：2010-10-21

  The present invention comprises compounds of Formula (I): wherein: X, R 1 , R 2 , R 3 , and R 4 are as defined in the specification. The invention also comprises a method of preventing, treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is type II diabetes, obesity and asthma. The invention also comprises a method of inhibiting CCR2 activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula (I).

  本发明涵盖了以下式（I）的化合物： 其中：X，R1，R2，R3和R4如规范中所定义。该发明还涵盖了一种预防、治疗或改善综合征、疾病或疾病的方法，其中所述综合征、疾病或疾病是II型糖尿病、肥胖和哮喘。该发明还涵盖了通过给哺乳动物施用至少一种式（I）化合物的治疗有效量来抑制CCR2活性的方法。
• 4'-Fluoro-4-{[4-(phenyl)cyclohexyl]amino}butyrophenones and the salts
  申请人：The Upjohn Company

  公开号：US03960961A1

  公开（公告）日：1976-06-01

  This invention relates to novel 4-phenylcyclohexylamines embraced by the formula ##SPC1## Wherein .about. is a generic expression denoting cis and trans stereoconfiguration and mixtures thereof; R is selected from the group consisting of alkyl of from one through four carbon atoms, fluorine, chlorine, bromine, trifluoromethyl, nitro and alkoxy of from one through four carbon atoms; R' and R.sup.1 are selected from the group consisting of hydrogen and alkyl of from one through four carbon atoms; R.sup.2 is selected from the group consisting of hydrogen, alkyl of from one through four carbon atoms, alkanoyl of from one through three carbon atoms, alkylsulfonyl of from one through three carbon atoms, arylsulfonyl of from six through ten carbon atoms, alkylcarbamoyl wherein alkyl is from one through four carbon atoms, alkoxycarbonyl wherein alkyl is from one through four carbon atoms, ring monosubstituted aroylalkyl wherein the substituents have the same meaning as R, above, aryl is from six through ten carbon atoms and alkyl is from one through six carbon atoms and bis (ring monosubstituted) arylalkyl wherein the substituents have the same meaning as R, above, aryl is from six through ten carbon atoms and alkyl is from one through six carbon atoms; R.sup.1 and R.sup.2 when taken together with --N< is a saturated heterocyclic amino radical selected from the group consisting of unsubstituted and monosubstituted pyrrolidino, piperidino, hexamethylenimino, morpholino and piperazino; and an acid addition salt thereof. It also relates to intermediates and processes for the preparation of the aforesaid novel compounds (1) and novel derivatives thereof. The systemic administration to humans and animals of the novel compounds (1) depresses their central nervous systems.

  这项发明涉及由以下式 embraced 的新型 4-苯基环己胺 ##SPC1## 其中 .about. 是一个通用表达式，表示顺式和反式立体构型及其混合物；R 选自由一至四个碳原子的烷基、氟、氯、溴、三氟甲基、硝基和由一至四个碳原子组成的烷氧基；R' 和 R.sup.1 选自由一至四个碳原子的氢和烷基；R.sup.2 选自由一至四个碳原子的氢、烷基、由一至三个碳原子组成的烷酰基、由一至三个碳原子组成的烷基磺酰基、由六至十个碳原子组成的芳基磺酰基、烷基氨基甲酰，其中烷基由一至四个碳原子组成，烷氧羰基，其中烷基由一至四个碳原子组成，环中单取代芳酰基烷基，其中取代基的含义与上述的 R 相同，芳基由六至十个碳原子，烷基由一至六个碳原子，以及双(环中单取代)芳基烷基，其中取代基的含义与上述的 R 相同，芳基由六至十个碳原子，烷基由一至六个碳原子；当 R.sup.1 和 R.sup.2 与 --N< 结合在一起时，是选自未取代和单取代吡咯烷基、哌啶基、六亚甲基基氮、吗啉基和哌嗪基的饱和杂环氨基基团；以及其酸盐。它还涉及制备上述新型化合物 (1) 及其新型衍生物的中间体和过程。将这些新型化合物 (1) 系统地给人类和动物静脉注射会抑制其中枢神经系统。
• A convenient chemical-microbial method for developing fluorinated pharmaceuticals
  作者：Tara V. Bright、Fay Dalton、Victoria L. Elder、Cormac D. Murphy、Neil K. O'Connor、Graham Sandford

  DOI：10.1039/c2ob27140k

  日期：——

  A significant proportion of pharmaceuticals are fluorinated and selecting the site of fluorine incorporation can be an important beneficial part a drug development process. Here we describe initial experiments aimed at the development of a general method of selecting optimum sites on pro-drug molecules for fluorination, so that metabolic stability may be improved. Several model biphenyl derivatives were transformed by the fungus Cunninghamella elegans and the bacterium Streptomyces griseus, both of which contain cytochromes P450 that mimic oxidation processes in vivo, so that the site of oxidation could be determined. Subsequently, fluorinated biphenyl derivatives were synthesised using appropriate Suzuki–Miyaura coupling reactions, positioning the fluorine atom at the pre-determined site of microbial oxidation; the fluorinated biphenyl derivatives were incubated with the microorganisms and the degree of oxidation assessed. Biphenyl-4-carboxylic acid was transformed completely to 4′-hydroxybiphenyl-4-carboxylic acid by C. elegans but, in contrast, the 4′-fluoro-analogue remained untransformed exemplifying the microbial oxidation – chemical fluorination concept. 2′-Fluoro- and 3′-fluoro-biphenyl-4-carboxylic acid were also transformed, but more slowly than the non-fluorinated biphenyl carboxylic acid derivative. Thus, it is possible to design compounds in an iterative fashion with a longer metabolic half-life by identifying the sites that are most easily oxidised by in vitro methods and subsequent fluorination without recourse to extensive animal studies.

  大部分药物含有氟元素，在药物开发过程中，选择氟元素的加入位置可能是一个有益的环节。在这里，我们描述了初始实验，旨在开发一种通用方法，选择前药分子上最佳的氟化位置，以提高代谢稳定性。通过含有细胞色素P450的真菌和细菌分别对几种联苯衍生物进行转化，这些细胞色素P450模拟了体内的氧化过程，从而确定了氧化位置。随后，利用适当的铃木-宫浦偶联反应合成了氟化联苯衍生物，将氟原子置于预定微生物氧化的位置；这些氟化联苯衍生物与微生物共培养，并评估了氧化程度。结果显示，联苯-4-羧酸被Cunninghamella elegans完全转化为4′-羟基联苯-4-羧酸，但4′-氟代衍生物保持不变，证明了微生物氧化-化学氟化的概念。2′-氟代和3′-氟代联苯-4-羧酸也能被转化，但速度比未氟化的联苯羧酸衍生物慢。因此，可以通过体外方法确定最容易氧化的位置，然后进行氟化，迭代设计代谢半衰期更长的化合物，无需依赖大量的动物研究。
• Piperazinyl-and piperidinyl-cyclohexanols
  申请人：Briston-Myers Squibb

  公开号：US05387593A1

  公开（公告）日：1995-02-07

  Novel piperazinyl- and piperidinyl-cyclohexanols of the following formula are useful as anxiolytic agents and have other psychotropic properties ##STR1##

  新型哌嗪基和哌啶基环己醇具有以下化学式，可用作抗焦虑药物，并具有其他精神药理特性。
• Piperazinyl-cyclohexanes and cyclohexenes
  申请人：Bristol-Myers Squibb Company

  公开号：US06153611A1

  公开（公告）日：2000-11-28

  Novel non-dopaminergic antiischemic compounds have Formula I: ##STR1## wherein R=R.sub.1 and is independently H, C.sub.1-4 alky C.sub.1-4 alkoxy, C.sub.1-4 trihaloalkyl or halogen, or R and R.sub.1 may be taken together to form an --O(CH.sub.2).sub.m O-- (m=1 or 2); X=a 3-indolyl, phenyl, naphthalenyl or 2-benzothiazolyl residue; n=0, 1, 2 or 3; ##STR2## R.sub.2 =R.sub.3 and is independently H or C.sub.1-4 alkyl; and R.sub.4 =phenyl, 2-thienyl, 2-quinolinyl, 4-pyridinyl or substituted phenyl.

  新型非多巴胺抗缺血化合物的化学式为：##STR1## 其中 R=R.sub.1，独立地为 H、C.sub.1-4 烷基、C.sub.1-4 烷氧基、C.sub.1-4 三卤代烷基或卤素，或者 R 和 R.sub.1 可以结合形成 --O(CH.sub.2).sub.m O-- (m=1 或 2)；X=3-吲哚基、苯基、萘基或 2-苯并噻唑基残基；n=0、1、2 或 3；##STR2## R.sub.2 =R.sub.3，独立地为 H 或 C.sub.1-4 烷基；而 R.sub.4 =苯基、2-噻吩基、2-喹啉基、4-吡啶基或取代苯基。