2-bromo-3',4'-bis(benzyloxy)acetophenone | 27628-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3',4'-bis(benzyloxy)acetophenone
• 英文别名: 3,4-bis(benzyloxy)-ω-bromoacetophenone；1-(3,4-bis(benzyloxy)phenyl)-2-bromoethanone；3,4-dibenzyloxy-α-bromoacetophenone；3',4'-bis(benzyloxy)-2-bromoacetophenone；α-bromo-3,4-dibenzyloxy-acetophenone；3,4-dibenzyloxyphenacyl bromide；1-[3,4-bis(phenylmethoxy)phenyl]-2-bromoethanone
• CAS: 27628-05-3
• 化学式: C₂₂H₁₉BrO₃
• 分子量: 411.295
• InChiKey: FWKNVYGFFGCWQY-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿；二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-3',4'-bis(benzyloxy)acetophenone 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 18.0h， 生成 1-(3,4-dihydroxyphenyl)-2-(β-isobutyramidoethyl)aminoethanol
  参考文献：
  名称：

  .beta.-Adrenoceptor stimulant properties of amidoalkylamino-substituted 1-aryl-2-ethanols and 1-(aryloxy)-2-propanols

  摘要：

  Parallel series of 2-[(2-amidoethyl)amino]-1-arylethanols and 1-[(2-amidoethyl)amino]-3-(aryloxy)-2-propanols have been prepared, and the compounds were tested as beta-adrenoceptor stimulants on the heart and circulation of the dog. The corresponding 2-(alkylamino)-1-arylethanols and 3-(alkylamino)-2-propanols have been tested for comparison and the structure-activity relationships (SAR) examined. The arylethanols are potent full agonists, showing selectivity for the heart relative to blood vessels, while the (aryloxy)propanols are even more cardioselective and are partial agonists. Within a narrow series of 1-[(amidoethyl)amino]-3-(4-hydroxyphenoxy)-2-propanols, careful examination of the SAR of the amide group showed that great variation in cardioselectivity and degree of agonism may be produce. From this study ICI 118587, N-[20[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-4-morpholinecarboxamide, was selected for its high cardioselectivity and 50% agonist properties. This compound in under clinical evaluation as a cardiac stimulant.

  DOI：

  10.1021/jm00135a015
• 作为产物：
  描述：

  1-[3,4-二(苯基甲氧基)苯基]乙酮 在 tetra-N-butylammonium tribromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到2-bromo-3',4'-bis(benzyloxy)acetophenone
  参考文献：
  名称：

  10th international symposium on the synthesis and applications of isotopes and isotopically labelled compounds-Wiley Young Scientist Awards Session 10, Tuesday, June 16, 2009

  摘要：

  以下是四位威尔利青年科学家奖得主中的三位的发言亮点。版权所有© 2010年，约翰·威利父子出版公司。

  DOI：

  10.1002/jlcr.1767

文献信息

• New Scaffold for Angiogenesis Inhibitors Discovered by Targeted Chemical Transformations of Wondonin Natural Products
  作者：Shuai Yu、Jedo Oh、Feng Li、Yongseok Kwon、Hyunkyung Cho、Jongheon Shin、Sang Kook Lee、Sanghee Kim

  DOI：10.1021/acsmedchemlett.7b00281

  日期：2017.10.12

  in a new scaffold with enhanced antiangiogenic activity and minimized cytotoxicity. One compound with this scaffold effectively inhibited hyaloid vessel formation in diabetic retinopathy mimic zebrafish model. The biological findings together suggested the potential of the scaffold as a lead structure for development of antiangiogenic drugs with novel functions and as a probe to elucidate new biological

  对馄饨素海洋天然产物的结构进行了翻新，以获得新的药物样支架。Wondonins具有新颖的抗血管生成特性，没有明显的细胞毒性。然而，馄饨蛋白的化学不稳定性和合成复杂性阻碍了它们作为新型抗血管生成剂的发展。使用基于结构的生物立体异构，将苯并二恶唑部分更改为苯并噻唑，并将咪唑部分替换为1,2,3-三唑。我们的努力导致了一种具有增强的抗血管生成活性和最小化细胞毒性的新型支架。具有这种支架的一种化合物在糖尿病性视网膜病模拟斑马鱼模型中有效抑制玻璃样血管的形成。
• <i>p</i>-Hydroxyphenacyl photoremovable protecting groups — Robust photochemistry despite substituent diversity
  作者：Richard S. Givens、Kenneth Stensrud、Peter G. Conrad、Abraham L. Yousef、Chamani Perera、Sanjeewa N. Senadheera、Dominik Heger、Jakob Wirz

  DOI：10.1139/v10-143

  日期：2011.2

  A broadly based investigation of the effects of a diverse array of substituents on the photochemical rearrangement of p-hydroxyphenacyl esters has demonstrated that common substituents such as F, MeO, CN, CO₂R, CONH₂, and CH₃have little effect on the rate and quantum efficiencies for the photo-Favorskii rearrangement and the release of the acid leaving group or on the lifetimes of the reactive triplet state. A decrease in the quantum yields across all substituents was observed for the release and rearrangement when the photolyses were carried out in buffered aqueous media at pHs that exceeded the ground-state pK_aof the chromophore where the conjugate base is the predominant form. Otherwise, substituents have only a very modest effect on the photoreaction of these robust chromophores.

  一项关于各种取代基对对羟基苯乙酯光化学重排影响的广泛研究表明，常见取代基（如 F、MeO、CN、CO2R、CONH2 和 CH3）对光-Favorskii 重排和酸离去基团释放的速率和量子效率影响很小，对反应三重态的寿命影响也很小。当光解在缓冲水介质中进行时，pH 值超过发色团的基态 pKao（其中共轭碱是主要形式），则释放和重排的量子产率在所有取代基中都会降低。否则，取代基对这些坚固发色团的光反应影响很小。
• New antihypertensive agents. I. Synthesis and antihypertensive activity of some 4-piperidylbenzimidazolinone derivatives.
  作者：HIROYUKI OBASE、NOBUHIRO NAKAMIZO、HARUKI TAKAI、MASAYUKI TERANISHI、KAZUHIRO KUBO、KATSUICHI SHUTO、YUTAKA KASUYA、HITOSHI KATO、KOKI SHIGENOBU、JUNICHI KURIHARA

  DOI：10.1248/cpb.30.462

  日期：——

  A series of 4-piperidylbenzimidazolinones, of formula I, has been synthesized. Selective syntheses of erythro and threo isomers of α-alkyl phenylethanolamines were investigated. Most members of the series have been shown to have antihypertensive effects in various animal models. Compounds 27 and 31 (threo isomers) showed the strongest hypotensive activities in the present screening series.

  一系列4-哌啶基苯并咪唑啉酮（I式）已被合成。对α-烷基苯乙醇胺的红、青异构体进行了选择性合成研究。该系列中的大多数成员已被证明在各种动物模型中具有抗高血压效果。在此次筛选系列中，化合物27和31（青异构体）显示出最强的降压活性。
• Esters
  申请人：Imperial Chemical Industries Limited

  公开号：US04423070A1

  公开（公告）日：1983-12-27

  The invention concerns di- and tri-esters derived from alkanoic, (cycloalkyl)alkanoic, benzoic or phenylalkanoic acids with N-(acylaminoalkyl)-dihydroxyphenylethanolamines, and pharmaceutically acceptable salts thereof; processes for their preparation and manufacture; and pharmaceutical compositions thereof. The esters are useful for the topical treatment of an area of inflammation affecting the skin of a warm-blooded animal. Representative esters of the invention are 1-[3,4-bis(pivaloyloxy)phenyl]-2-[2-(2-phenylacetamido)ethylamino]-ethanol , 1-[3,4-bis(pivaloyloxy)phenyl]-2-[1,1-dimethyl-2-(2-phenoxyacetamido)-eth ylamino]-ethanol, and the hydrochlorides and hydrobromides thereof.

  该发明涉及从烷酸、(环烷基)烷酸、苯甲酸或苯基烷酸与N-(酰胺基烷基)-二羟基苯乙醇胺衍生的二酯和三酯，以及其药用可接受的盐；它们的制备和生产过程；以及它们的药物组合物。这些酯对于治疗影响温血动物皮肤的炎症区域具有用处。该发明的代表性酯包括1-[3,4-双(偏酰氧基)苯基]-2-[2-(2-苯乙酰胺基)乙基氨基]-乙醇，1-[3,4-双(偏酰氧基)苯基]-2-[1,1-二甲基-2-(2-苯氧基乙酰胺基)-乙基氨基]-乙醇，以及它们的盐酸盐和溴化盐。
• Optically Pure Isoproterenol Analogues With Side Chains Containing an Amide Bond: Synthesis and biological properties
  作者：Hans P. Märki、Yvo Crameri、Rainer Eigenmann、Anna Krasso、Henri Ramuz、Karl Bernauer、Murray Goodman、Kenneth L. Melmon

  DOI：10.1002/hlca.19880710204

  日期：1988.3.16

  The isoproterenol analogues 4a and 4b, synthesized as mixtures of Diastereoisomers, were shown to possess very potent β-adrenoceptor agonistic activity. Therefore, the four possible diastereoisomers of 4a have been synthesized and tested for inotropic activity. The (6R, 2′R)-diastereoisomer turned out to be the most interesting one. Consequently, also (6R,2′R)-4b has been prepared and tested. For the

  合成为非对映异构体混合物的异丙肾上腺素类似物4a和4b具有非常强的β-肾上腺素受体激动活性。因此，已经合成了4a的四种可能的非对映异构体，并测试了其正性活性。的（6 - [R，2' - [R）-diastereoisomer原来是最有趣的一个。因此，也已经制备并测试了（6 R，2'R）-4b。对于非对映选择性合成，已阐述了三种变体：（i）环氧化物12与胺27的偶联（方案6）；（二）将活化的二醇17与胺22偶联（方案8）；（iii）氨基酮31的非对映选择性氢化（方案7）。（6 R，2'R）-4a和（6 R，2'R）-4b在静脉内和口服后均表现出持久的正性肌力活性，并且其效力至少是rac的三倍-异丙肾上腺素。在麻醉的狗中，观察到良好的正性肌力和正性变时作用的分离。但是，在清醒的狗中，心率和收缩力增加的幅度相同（可能是由于反射性心动过速）。