(E/Z)-5-bromo-2(prop-1-enyl)phenol | 1014625-90-1

• 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: (E/Z)-5-bromo-2(prop-1-enyl)phenol
• 英文别名: 5-Bromo-2-(propenyl)-phenol；5-bromo-2-prop-1-enylphenol
• CAS: 1014625-90-1
• 化学式: C₉H₉BrO
• 分子量: 213.074
• InChiKey: ZFNXQHGAXOPNFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E/Z)-5-bromo-2(prop-1-enyl)phenol 、 4-甲氧基苯硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 (Z)-5-(4-methoxyphenyl)-2-(prop-1-enyl)phenol 、 (E)-5-(4-methoxyphenyl)-2-(prop-1-enyl)phenol
  参考文献：
  名称：

  Monoaryl-Substituted Salicylaldoximes as Ligands for Estrogen Receptor β

  摘要：

  Salicylaldoximes possess a hydrogen-bonded pseudocyclic A' ring in place of the typical phenolic A ring that is characteristic of most estrogen receptor (ER) ligands. Monoaryl-substituted salicylaldoximes were obtained by replacing the phenol moiety (ring A) of the ER beta pharmacophore with the pseudocycle A' ring, which has previously been shown to behave as a bioequivalent of phenols in nonselective ER ligands. In this series, small substituents (CH(3), CN, Cl) were introduced into the central phenyl scaffold. An efficient sequential halogen-selective double cross-coupling reaction was developed for the synthesis of the methylsubstituted ER ligand. The measured ER beta affinity proved to be very sensitive to the effect of central core substituents. The binding affinities of the compounds herein reported were in good agreement with the results of computational docking analysis. The chloro-substituted derivative showed the highest beta affinity and selectivity, and it also proved to be an ER beta partial agonist with an EC(50) of 11 nM.

  DOI：

  10.1021/jm701396g
• 作为产物：
  描述：

  potassium tert-butylate 、 4-溴-2-羟基苯甲醛 在 乙基三苯基溴化膦 氯化铵 、 水 、 乙醚 、 magnesium sulfate 、 正庚烷 、 ethyl acetate heptane 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 反应 24.0h， 以to yield 5-bromo-2-(propenyl)-phenol as a yellow oil的产率得到(E/Z)-5-bromo-2(prop-1-enyl)phenol
  参考文献：
  名称：

  Heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators

  摘要：

  本发明涉及公式（I）的苯基取代的杂环基衍生物，其中Z，n，m，R1，R2，R3，R4，R5，R6，R7和R8如描述中所述，以及它们在各种前列腺素介导的疾病和障碍的治疗中作为前列腺素受体调节剂的用途，特别是作为前列腺素D2受体调节剂，以及包含这些化合物的制药组合物和它们的制备方法。

  公开号：

  US09255090B2

文献信息

• [EN] HETEROCYCLYL DERIVATIVES AND THEIR USE AS PROSTAGLANDIN D2 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS HÉTÉROCYCLYLE ET LEUR UTILISATION COMME MODULATEURS DE RÉCEPTEURS DE LA PROSTAGLANDINE D2
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2013093842A1

  公开（公告）日：2013-06-27

  The present invention relates to phenyl-substituted heterocyclyl derivatives of the formula (I) wherein Z, n, m, R1, R2, R3, R4, R5, R6, R7 and R8 are as described in the description and their use as prostaglandin receptor modulators, most particularly as prostaglandin D2 receptor modulators, in the treatment of various prostaglandin-mediated diseases and disorders, to pharmaceutical compositions containing these compounds and to processes for their preparation.

  本发明涉及式(I)的苯基取代杂环基衍生物，其中Z、n、m、R1、R2、R3、R4、R5、R6、R7和R8如描述中所述，并且它们作为前列腺素受体调节剂的用途，尤其作为前列腺素D2受体调节剂，在治疗各种前列腺素介导的疾病和紊乱中的用途，以及含有这些化合物的药物组合物和其制备方法。
• Heterocyclyl Derivatives and their use as Prostaglandin D2 Receptor Modulators
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：US20150252036A1

  公开（公告）日：2015-09-10

  The present invention relates to phenyl-substituted heterocyclyl derivatives of the formula (I), wherein Z, n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as described in the description and their use as prostaglandin receptor modulators, most particularly as prostaglandin D 2 receptor modulators, in the treatment of various prostaglandin-mediated diseases and disorders, to pharmaceutical compositions containing these compounds and to processes for their preparation.

  本发明涉及公式（I）的苯基取代杂环基衍生物，其中Z，n，m，R1，R2，R3，R4，R5，R6，R7和R8如描述中所述，并且它们作为前列腺素受体调节剂的用途，特别是作为前列腺素D2受体调节剂，在治疗各种前列腺素介导的疾病和疾患中使用，以及包含这些化合物的制药组合物和它们的制备过程。
• Antitumor compositions and methods of treatment
  申请人：ELI LILLY AND COMPANY

  公开号：EP0560554A2

  公开（公告）日：1993-09-15

  This invention provides the use of certain benzofuransulfonamide, benzothiophenesulfonamide, and indolesulfonamide derivatives in the treatment of susceptible neoplasms in mammals. Also provided are certain novel benzofuransulfonamide and benzothiophenesulfonamide derivatives and their pharmaceutical formulations. This invention further provides processes for producing the compounds of the invention.

  本发明提供了某些苯并呋喃磺酰胺、苯并噻吩磺酰胺和吲哚磺酰胺衍生物在治疗哺乳动物易感肿瘤中的用途。本发明还提供了某些新型苯并呋喃磺酰胺和苯并噻吩磺酰胺衍生物及其药物制剂。本发明进一步提供了生产本发明化合物的工艺。
• HETEROCYCLYL DERIVATIVES AND THEIR USE AS PROSTAGLANDIN D2 RECEPTOR MODULATORS
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP2794563A1

  公开（公告）日：2014-10-29
• US5169860A
  申请人：——

  公开号：US5169860A

  公开（公告）日：1992-12-08