2-bromo-(3-ethyl-4-hydroxyphenyl)ethanone | 73898-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-(3-ethyl-4-hydroxyphenyl)ethanone
• 英文别名: 2-Bromo-1-(3-ethyl-4-hydroxyphenyl)ethanone
• CAS: 73898-24-5
• 化学式: C₁₀H₁₁BrO₂
• 分子量: 243.1
• InChiKey: FCDZBFGPNCCYGD-UHFFFAOYSA-N

物化性质

• 沸点：
  365.5±32.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-bromo-(3-ethyl-4-hydroxyphenyl)ethanone 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 丁酮 为溶剂， 25.0 ℃ 、98.06 kPa 条件下， 反应 110.0h， 生成 4-(2-Amino-1-hydroxyethyl)-2-ethylphenol;hydrochloride
  参考文献：
  名称：

  Synthesis and structure-activity relationships among .alpha.-adrenergic receptor agonists of the phenylethanolamine type

  摘要：

  Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for alpha-adrenergic stimulant activity. In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, chlohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups. The other series is meta hydroxylated with the para position substituted by the same groups. The influence of these groups upon the alpha-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine, norepinephrine, and norphenylephrine. It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental. The most active compound, alpha-(aminomethyl)(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundredth the affinity and the same intrinsic activity as norepinephrine.

  DOI：

  10.1021/jm00181a008
• 作为产物：
  描述：

  乙基苯酚 在 三氯化铝 、 1,4-dioxane dibromide 作用下， 以 1,4-二氧六环 、 二硫化碳 、 乙醚 为溶剂， 反应 15.0h， 生成 2-bromo-(3-ethyl-4-hydroxyphenyl)ethanone
  参考文献：
  名称：

  Synthesis and structure-activity relationships among .alpha.-adrenergic receptor agonists of the phenylethanolamine type

  摘要：

  Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for alpha-adrenergic stimulant activity. In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, chlohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups. The other series is meta hydroxylated with the para position substituted by the same groups. The influence of these groups upon the alpha-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine, norepinephrine, and norphenylephrine. It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental. The most active compound, alpha-(aminomethyl)(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundredth the affinity and the same intrinsic activity as norepinephrine.

  DOI：

  10.1021/jm00181a008

文献信息

• QUINUCLIDINE DERIVATIVES AS SQUALENE SYNTHASE INHIBITORS
  申请人：ZENECA LIMITED

  公开号：EP0654032A1

  公开（公告）日：1995-05-24
• US5691349A
  申请人：——

  公开号：US5691349A

  公开（公告）日：1997-11-25
• [EN] QUINUCLIDINE DERIVATIVES AS SQUALENE SYNTHASE INHIBITORS<br/>[FR] DERIVES DE LA QUINUCLIDINE UTILISES COMME INHIBITEURS DE LA SQUALENE SYNTHETASE
  申请人：ZENECA LIMITED

  公开号：WO1994003451A1

  公开（公告）日：1994-02-17

  (EN) Quinuclidine derivatives of formula (I), and their pharmaceutically acceptable salts, in which: R1 is hydrogen or hydroxy; R2 is hydrogen; or R1 and R2 are joined together so that CR1-CR2 is a double bond; X is selected from -CH2CH2-, -CH=CH-, -C=C-, -CH2O-, -OCH2-, -CH2NH-, -NHCH2-, -CH2CO-, -COCH2-, -CH2S(O)n- and -S(O)nCH2- wherein n is 0, 1 or 2; and Ar is phenyl which may be optionally unsubstituted or substituted by one or more substituents such as halogeno, hydroxy, amino, nitro, cyano, carboxy, carbamoyl, alkyl, alkenyl, alkynyl, alkoxy, alkylamino, dialkylamino, N-alkylcarbamoyl, N,N-di-alkylcarbamoyl, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, halogeno alkyl, alkanoylamino, alkylenedioxy, alkanoyl and oxime derivatives thereof and O-alkyl ethers of said oximes; provided that when X is selected from -OCH2-, -NHCH2-, and -SCH2-, R1 is not hydroxy; inhibit squalene synthase and are useful in treating diseases or medical conditions in which inhibition of squalene synthase is desirable. The use of such heterocyclic derivatives in treating conditions such as hypercholesterolemia, and atherosclerosis is referred to as well as novel compounds, processes for their preparation and pharmaceutical compositions containing them.(FR) L'invention concerne des dérivés de la quinuclidine de la formule (I) et leurs sels acceptables sur le plan pharmaceutique. Dans cette formule, R1 est un hydrogène ou un hydroxyle; R2 est un hydrogène; ou R1 et R2 sont réunis ensemble, de sorte que CR1-CR2 est une double liaison; X est choisi parmi -CH2-CH2-, -CH=CH-, -C=C-, -CH2O-, -OCH2-, -CH2NH-, -NHCH2-, -CH2CO-, -COCH2-, -CH2S(O)n- et S(O)nCH2-, où n est égal à 0, 1 ou 2; et Ar est un phényle qui peut être le cas échéant non substitué ou substitué par un ou plusieurs substituants tels que halogéno, hydroxy, amino, nitro, cyano, carboxy, carbamoyle, alkyle, alcényle, alcynyle, alcoxy, alkylamino, dialkylamino, N-alkylcarbamoyle, N,N-di-alkylcarbamoyle, alcoxycarbonyle, alkylthio, alkylsulfinyle, alkylsulfonyle, halogénoalkyle, alcanoylamino, alkylènedioxy, alcanoyle et les dérivés oxime correspondants ainsi que les O-alkyle esters desdites oximes. Une condition à satisfaire est que lorsque X est choisi parmi -OCH2-, NHCH2- et -SCH2-, R1 ne doit pas être un hydroxy. Ces composés inhibent la squalène synthétase et ils sont utiles pour traiter des maladies ou des états pahtologiques dans lesquels il est souhaitable d'inhiber la squalène synthétase. L'invention concerne l'utilisation de tels dérivés hétérocycliques pour traiter des maladies comme l'hypercholestérolémie et l'artériosclérose, ainsi que de nouveaux composés, des procédés pour leur préparation et des compositions pharmaceutiques les contenant.
• Synthesis and structure-activity relationships among .alpha.-adrenergic receptor agonists of the phenylethanolamine type
  作者：Gerard Leclerc、Jean Claude Bizec、Nicole Bieth、Jean Schwartz

  DOI：10.1021/jm00181a008

  日期：1980.7

  Nineteen arylethanolamine derivatives related to norepinephrine were prepared and tested for alpha-adrenergic stimulant activity. In one series the analogues possess a p-hydroxy function, while the meta position is substituted by methyl, ethyl, isopropyl, chlohexyl, fluoro, chloro, iodo, carboxy, carbomethoxy, and methylsulfamido groups. The other series is meta hydroxylated with the para position substituted by the same groups. The influence of these groups upon the alpha-adrenergic activity is discussed, and the compounds are compared to octopamine, normetanephrine, norepinephrine, and norphenylephrine. It has been found that the introduction of an isopropyl, cyclohexyl, and fluoro group in the meta position of octopamine improves its affinity by three, five, and six times, respectively, whereas when these groups are introduced in the para position of norphenylephrine their effects are always detrimental. The most active compound, alpha-(aminomethyl)(4-fluoro-3-hydroxyphenyl)methanol (44), has about one-hundredth the affinity and the same intrinsic activity as norepinephrine.