1-(3-溴-5-异恶唑基)-2-溴乙醇 | 76596-55-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 1-(3-溴-5-异恶唑基)-2-溴乙醇
• 英文名称: 1-(3-bromo-5-isoxazolyl)-2-bromoethanol
• 英文别名: 2-bromo-1-(3-bromoisoxazol-5-yl)ethanol；1-(3-bromo-isoxazol-5-yl)-2-bromoethanol；1-(3-bromoisoxazol-5-yl)-2-bromoethanol；2-bromo-1-(3-bromo-1,2-oxazol-5-yl)ethanol
• CAS: 76596-55-9
• 化学式: C₅H₅Br₂NO₂
• 分子量: 270.908
• InChiKey: WYIIEBIFVAUGEW-UHFFFAOYSA-N

物化性质

• 熔点：
  0.5 °C
• 沸点：
  165 °C(Press: 0.1 Torr)
• 密度：
  2.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-溴-5-异恶唑基)-2-溴乙醇 以93的产率得到溴沙特罗
  参考文献：
  名称：

  1-(3-Bromo-isoxazol-5-yl)-2-tert.butylaminoethanol

  摘要：

  本发明公开了一种新的异噁唑衍生物及其制备方法。公开了具有治疗活性的1-(3-溴异噁唑-5-基)-2-叔丁基氨基乙醇，特别是具有支气管扩张作用，以及从3-溴-5-异噁唑羧酸制备该化合物的方法。还公开了新的中间体化合物和含有新异噁唑衍生物的药物组合物。

  公开号：

  US04276299A1
• 作为产物：
  描述：

  1-(3-溴-5-异噁唑)-乙酮 在 sodium tetrahydroborate 、 溴 作用下， 以 甲醇 、 氯仿 、 溶剂黄146 为溶剂， 反应 1.17h， 生成 1-(3-溴-5-异恶唑基)-2-溴乙醇
  参考文献：
  名称：

  Chiarino; Fantucci; Carenzi, Farmaco, Edizione Scientifica, 1986, vol. 41, # 6, p. 440 - 453

  摘要：

  DOI：

文献信息

• Disubstituted piperidine derivatives as neuroprotective agents
  申请人：Pharmacia & Upjohn S.p.A.

  公开号：US05968955A1

  公开（公告）日：1999-10-19

  A Disubstituted piperidine compounds of formula (I), wherein R.sub.1 is hydrogen; bromo; chloro; a linear or branched C.sub.1 -C.sub.5 alkyl group; a linear or branched C.sub.1 -C.sub.5 alkoxy group; or an optionally substituted phenyl group; R.sub.2 is hydrogen, a linear or branched C.sub.1 -C.sub.5 alkyl group or an optionally substituted phenyl group; X is CH.sub.2, C.dbd.O, CHOH or C.dbd.NOH; R.sub.3 is hydrogen or a linear or branched C.sub.1 -C.sub.5 alkyl group; Y is a (CH.sub.2).sub.n group in which n is an integer from 0 to 4, CHOH, C.dbd.O or CH-A wherein A is an optionally substituted phenyl group; A is an optionally substituted phenyl group; W is hydrogen or hydroxy; stereoisomers thereof and their pharmaceutically acceptable salts. The compounds possess selective neuroprotective activity and are useful in the treatment of an acute or a degenerative CNS disease. A process is described for preparing the compounds and pharmaceutical compositions containing them.

  一种公式为(I)的二取代哌啶化合物，其中R.sub.1为氢; 溴; 氯; 线性或支链C.sub.1-C.sub.5烷基; 线性或支链C.sub.1-C.sub.5烷氧基; 或者是可选取代的苯基; R.sub.2为氢，线性或支链C.sub.1-C.sub.5烷基或可选取代的苯基; X为CH.sub.2，C.dbd.O，CHOH或C.dbd.NOH; R.sub.3为氢或线性或支链C.sub.1-C.sub.5烷基; Y为(CH.sub.2).sub.n基团，其中n是0到4的整数，CHOH，C.dbd.O或CH-A，其中A是可选取代的苯基; A是可选取代的苯基; W为氢或羟基; 其立体异构体及其药学上可接受的盐。该化合物具有选择性神经保护活性，可用于治疗急性或退行性中枢神经系统疾病。描述了制备该化合物和含有它们的制药组合物的过程。
• Chemoenzymatic synthesis of chiral isoxazole derivatives
  作者：Marco De Amici、Carlo De Micheli、Giacomo Carrea、Sandro Spezia

  DOI：10.1021/jo00272a037

  日期：1989.5
• De Amici; Conti; Dallanoce, Medicinal Chemistry Research, 2000, vol. 10, # 2, p. 69 - 80
  作者：De Amici、Conti、Dallanoce、Kassi、Castellano、Stefancich、De Micheli

  DOI：——

  日期：——
• Novel chiral isoxazole derivatives: Synthesis and pharmacological characterization at human β-adrenergic receptor subtypes
  作者：Clelia Dallanoce、Fabio Frigerio、Marco De Amici、Sandra Dorsch、Karl-Norbert Klotz、Carlo De Micheli

  DOI：10.1016/j.bmc.2007.01.056

  日期：2007.4

  Isoxazole derivative (+/-)-4 and the three pairs of stereoisomeric 3-bromo-isoxazolyl amino alcohols (S,R)-(-)-7a/(R,R)(+)-7b, (S, R)-(-)-8a/(R, R)-(+)-8b, and (S, R)-(-)-9a/(R, R)-(+)-9b were synthesized and assayed for their affinity and efficacy at human beta(1)-, beta(2)-, and beta(3)-adrenergic receptors (beta-ARs) in membranes from Chinese hamster ovary (CHO) cells stably transfected with the respective receptor subtype. Whereas derivative ()-4 did not bind at all three P-ARs, stereoisomers (S, R)-7a-(S, R)-9a behaved as high-affinity ligands at beta(1)- and, particularly, at beta(2)-ARs (K-i 2.82-66.7 nM). The Ki values of isomers (R,R)-7b-(R,R)-9b at beta(1)- and beta(2)-subtypes were about 30-100 times higher than those of their (S, R)-7a-9a counterparts, indicating a sizable stereochemical effect. The affinity at beta(3)-ARs was negligible for all the investigated compounds. When submitted to a functional assay, the three stereoisomeric pairs showed a comparable pattern of efficacy at all three beta-AR subtypes. The highest value of efficacy (75-90%) was observed at beta(2)-ARs, whereas all compounds behaved as partial agonists (30-60%) at the beta(3)-subtype. The lowest degree of efficacy (15-35%) was found at beta(1)-ARs. The affinity/efficacy profile of the derivatives under study has been compared with that of the two model compounds, Broxaterol [(+/-)-1] and BRL 37344 [(+/-)-6]. (c) 2007 Elsevier Ltd. All rights reserved.
• J. Org. Chem. 1989, 54, 2646-2650
  作者：

  DOI：——

  日期：——