2-chloro-4-(4-fluorophenoxy)phenol | 139034-82-5

• 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: 2-chloro-4-(4-fluorophenoxy)phenol
• CAS: 139034-82-5
• 化学式: C₁₂H₈ClFO₂
• 分子量: 238.646
• InChiKey: GHRRFWAEFHLHAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-4-(4-fluorophenoxy)phenol 在 sodium hydroxide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 12.0h， 生成 (R)-7-{3-[2-Chloro-4-(4-fluoro-phenoxy)-phenoxy]-propoxy}-2-methyl-chroman-2-carboxylic acid
  参考文献：
  名称：

  (2R)-2-Methylchromane-2-carboxylic acids: Discovery of selective PPARα agonists as hypolipidemic agents

  摘要：

  A SAR study was conducted on chromane-2-carboxylic acid toward selective PPAR alpha agonisim. As a result, highly potent, and selective PPAR alpha agonists were discovered. The optimized compound 43 exhibited robust lowering of total cholesterol levels in hamster and dog animal models. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.028
• 作为产物：
  描述：

  4-(4-氟苯氧基)苯甲醛 在 二异丁胺 、 磺酰氯 、 间氯过氧苯甲酸 作用下， 生成 2-chloro-4-(4-fluorophenoxy)phenol
  参考文献：
  名称：

  (2R)-2-Methylchromane-2-carboxylic acids: Discovery of selective PPARα agonists as hypolipidemic agents

  摘要：

  A SAR study was conducted on chromane-2-carboxylic acid toward selective PPAR alpha agonisim. As a result, highly potent, and selective PPAR alpha agonists were discovered. The optimized compound 43 exhibited robust lowering of total cholesterol levels in hamster and dog animal models. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.028

文献信息

• Carbamic acid derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US05393885A1

  公开（公告）日：1995-02-28

  Compounds of the formula ##STR1## in which R.sub.1 is halogen, C.sub.1 -C.sub.3 alkyl, halo-C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, halo-C.sub.1 -C.sub.3 alkoxy or cyano and/or two substituents R.sub.1 which are bonded to adjacent C atoms of the phenyl ring together are --O--CH.sub.2 --O--; R.sub.2 is hydrogen, halogen or methyl; R.sub.3 is fluorine, chlorine, bromine or C.sub.1 -C.sub.3 alkyl; R.sub.4 is hydrogen or C.sub.1 -C.sub.3 alkyl; either R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, ##STR2## --COCO--R.sub.8,--CO--R.sub.9 or S(O).sub.m --N(R.sub.10)--COO--R.sub.11 and R.sub.6 is C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkenyl, halo-C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.5 alkynyl, halo-C.sub.3 -C.sub.5 alkynyl, C.sub.1 -C.sub.3 alkoxy-C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted phenyl; or R.sub.5 and R.sub.6 together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.7 is hydrogen, halogen or C.sub.1 -C.sub.3 alkyl; R.sub.8 is C.sub.1 -C.sub.8 alkoxy or --N(R.sub.12).sub.2 ; R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, --N(R.sub.13).sub.2 or C.sub.1 -C.sub.4 alkoxy; R.sub.10 is C.sub.1 -C.sub.3 alkyl; R.sub.11 is C.sub.1 -C.sub.6 alkyl; R.sub.12 radicals independently of one another are C.sub.1 -C.sub.4 alkyl; R.sub.13 radicals independently of one another are C.sub.1 -C.sub.4 alkyl; m is the number 0, 1 or 2; n is the number 0, 1, 2 or 3 where, if n is 2 or 3, the radicals R.sub.1 can be identical or different; X is O, S, CH.sub.2, CO or --O--CH.sub.2 --; Y is O or S; and Z is O or S, with the exception of 1-(2-fluoro-4-phenoxyphenoxy)-2-ethylaminocarbonyloxyethane, in free form or in salt form, can be used as agrochemical active ingredients and can be prepared in a manner known per se.

  公式为##STR1##的化合物，其中R.sub.1是卤素，C.sub.1-C.sub.3烷基，卤代C.sub.1-C.sub.3烷基，C.sub.1-C.sub.3烷氧基，卤代C.sub.1-C.sub.3烷氧基或氰基，和/或与苯环相邻的C原子相连的两个R.sub.1取代基一起是--O--CH.sub.2--O--; R.sub.2是氢，卤素或甲基; R.sub.3是氟，氯，溴或C.sub.1-C.sub.3烷基; R.sub.4是氢或C.sub.1-C.sub.3烷基; R.sub.5是氢，C.sub.1-C.sub.4烷基，##STR2## --COCO--R.sub.8，--CO--R.sub.9或S(O).sub.m--N(R.sub.10)--COO--R.sub.11，R.sub.6是C.sub.1-C.sub.6烷基，卤代C.sub.1-C.sub.4烷基，C.sub.2-C.sub.6烯基，卤代C.sub.3-C.sub.4烯基，C.sub.3-C.sub.5炔基，卤代C.sub.3-C.sub.5炔基，C.sub.1-C.sub.3烷氧基-C.sub.1-C.sub.3烷基，C.sub.3-C.sub.6环烷基，未取代或取代的苯基; 或R.sub.5和R.sub.6一起是--(CH.sub.2).sub.4--或--(CH.sub.2).sub.5--; R.sub.7是氢，卤素或C.sub.1-C.sub.3烷基; R.sub.8是C.sub.1-C.sub.8烷氧基或--N(R.sub.12).sub.2; R.sub.9是C.sub.1-C.sub.4烷基，C.sub.3-C.sub.6环烷基，--N(R.sub.13).sub.2或C.sub.1-C.sub.4烷氧基; R.sub.10是C.sub.1-C.sub.3烷基; R.sub.11是C.sub.1-C.sub.6烷基; R.sub.12基团彼此独立地是C.sub.1-C.sub.4烷基; R.sub.13基团彼此独立地是C.sub.1-C.sub.4烷基; m是数字0、1或2; n是数字0、1、2或3，其中如果n是2或3，则基团R.sub.1可以相同或不同; X是O，S，CH.sub.2，CO或--O--CH.sub.2--; Y是O或S; Z是O或S，但1-(2-氟-4-苯氧基苯氧基)-2-乙基氨基甲酰氧乙烷，无论是自由形式还是盐形式，可以用作农药活性成分，并可以按照已知的方法制备。
• Design and synthesis of potent and subtype-selective PPARα agonists
  作者：Ranjit C. Desai、Edward Metzger、Conrad Santini、Peter T. Meinke、James V. Heck、Joel P. Berger、Karen L. MacNaul、Tian-quan Cai、Samuel D. Wright、Arun Agrawal、David E. Moller、Soumya P. Sahoo

  DOI：10.1016/j.bmcl.2005.12.022

  日期：2006.3

  Beginning with a moderately potent PPAR gamma agonist 9, a series of potent and highly subtype-selective PPAR alpha agonists was identified through a systematic SAR study. Based on the results of the efficacy studies in the hamster and dog models of dyslipidemia and the desired pharmacokinetic data, the optimized compound 39 was selected for further profiling. (C) 2006 Elsevier Ltd. All rights reserved.
• (2<i>R</i>)-2-Ethylchromane-2-carboxylic Acids:  Discovery of Novel PPARα/γ Dual Agonists as Antihyperglycemic and Hypolipidemic Agents
  作者：Hiroo Koyama、Daniel J. Miller、Julia K. Boueres、Ranjit C. Desai、A. Brian Jones、Joel P. Berger、Karen L. MacNaul、Linda J. Kelly、Thomas W. Doebber、Margaret S. Wu、Gaochao Zhou、Pei-ran Wang、Marc C. Ippolito、Yu-Sheng Chao、Arun K. Agrawal、Ronald Franklin、James V. Heck、Samuel D. Wright、David E. Moller、Soumya P. Sahoo

  DOI：10.1021/jm030621d

  日期：2004.6.1

  A series of chromane-2-carboxylic acid derivatives was synthesized and evaluated for PPAR agonist activities. A structure-activity relationship was developed toward PPARalpha/gamma dual agonism. As a result, (2R)-7-3-[2-chloro-4-(4-fluorophenoxy)phenoxy]propoxy}-2-ethylchromane-2-carboxylic acid (48) was identified as a potent, structurally novel, selective PPARalpha/gamma dual agonist. Compound 48 exhibited substantial antihyperglycemic and hypolipidemic activities when orally administered in three different animal models: the db/db mouse type 2 diabetes model, a Syrian hamster lipid model, and a dog lipid model.
• Carbamidsäurederivate und ihre Verwendung als Pestizide
  申请人：Novartis AG

  公开号：EP0584046B1

  公开（公告）日：1998-10-07
• US5393885A
  申请人：——

  公开号：US5393885A

  公开（公告）日：1995-02-28