3-[(对乙酰氨基)苯氧基]-1,2-环氧丙烷 | 6597-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-[(对乙酰氨基)苯氧基]-1,2-环氧丙烷
• 英文名称: 1-(4-acetamidophenoxy)-2,3-epoxypropane
• 英文别名: 4'-(2,3-epoxypropoxy)acetanilide；1-(p-Acetamidophenoxy)-2,3-epoxypropan；1-(p-acetamino-phenoxy)-2,3-epoxy-propane；N-[4-(oxiran-2-ylmethoxy)phenyl]acetamide
• CAS: 6597-75-7
• 化学式: C₁₁H₁₃NO₃
• mdl: MFCD00799226
• 分子量: 207.229
• InChiKey: OQAKYHCGYGLHAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  122 °C
• 沸点：
  423.4±20.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

制备方法与用途

化学性质：结晶状，熔点为115-120℃。
用途：作为心得宁的中间体。
生产方法：通过在碱性条件下对乙酰氨基苯酚与环氧氯丙烷进行缩合（醚化）反应制得。

反应信息

• 作为反应物：
  描述：

  3-[(对乙酰氨基)苯氧基]-1,2-环氧丙烷 在 盐酸 、 sodium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 15.0h， 生成 2-[4-[[2-[4-[3-[benzyl(propan-2-yl)amino]-2-hydroxypropoxy]anilino]-2-oxoethyl]amino]butylamino]-N-[4-[3-[benzyl(propan-2-yl)amino]-2-hydroxypropoxy]phenyl]acetamide
  参考文献：
  名称：

  .beta.-Adrenoceptor antagonist activity of bivalent ligands. 1. Diamide analogs of practolol.

  摘要：

  Two series of bivalent ligands (P-X-P) containing the (R,S)-3-[(4-aminoaryl)oxy]-1-(isopropylamino)propan-2-ol pharmacophore and a connecting alpha,omega-dicarbonylpoly(methylene) [X = -OC(CH2)nCO-] or alpha,omega-N,N'-bis(carbonylmethylene) polymethylenediamine [X = -OCCH2NH(CH2)nNHCH2CO-] spanner were synthesized and evaluated for beta-adrenoceptor antagonist activity in rat heart and lung membrane preparations. The target compounds were obtained as a mixture of stereoisomers in modest yields by using a three to four step sequence beginning with N-benzylpractolol. The results from the competitive binding studies indicated that binding affinity increased by a factor of up to 160 by increasing the length of the group spanning the pharmacophore moieties. Modest increases in cardioselectivity were also obtained. The data suggest that further increases in spanner length and lipophilicity and optical resolution may improve the potential of a labeled bivalent beta 1-adrenoceptor antagonist to function as a myocardial imaging agent.

  DOI：

  10.1021/jm00387a025
• 作为产物：
  描述：

  N-Phenylacetohydroxamic acid 在 苯基溴化硒 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 3-[(对乙酰氨基)苯氧基]-1,2-环氧丙烷
  参考文献：
  名称：

  Redox‐Neutral Selenium‐Catalysed Isomerisation of para ‐Hydroxamic Acids into para ‐Aminophenols

  摘要：

  AbstractA selenium‐catalysed para‐hydroxylation of N‐aryl‐hydroxamic acids is reported. Mechanistically, the reaction comprises an N−O bond cleavage and consecutive selenium‐induced [2,3]‐rearrangement to deliver para‐hydroxyaniline derivatives. The mechanism is studied through both 18O‐crossover experiments as well as quantum chemical calculations. This redox‐neutral transformation provides an unconventional synthetic approach to para‐aminophenols.

  DOI：

  10.1002/anie.202100801

文献信息

• Synthesis and pharmacological evaluation of piperidine (piperazine)-amide substituted derivatives as multi-target antipsychotics
  作者：Ling Huang、Lanchang Gao、Xiaohua Zhang、Lei Yin、Jintao Hu、Ting Song、Yin Chen

  DOI：10.1016/j.bmcl.2020.127506

  日期：2020.10

  We report the optimisation of a series of novel amide-piperidine (piperazine) derivatives using the multiple ligand approach with dopamine and serotonin receptors. Of the derivatives, compound 11 exhibited high affinity for the D2, 5-HT1A, and 5-HT2A receptors, but low affinity for the 5-HT2C and histamine H1 receptors and human ether-a-go-go-related gene (hERG) channels. In vivo, compound 11 reduced

  我们报告了与多巴胺和5-羟色胺受体的多配体方法一系列新型酰胺-哌啶（哌嗪）衍生物的优化。在衍生物中，化合物11显示出高亲和力为d 2，5-HT 1A和5-HT 2A受体，但低亲和性对5-HT 2C和组胺H 2 1受体和人ether-A-GO-中间人相关基因（hERG）通道。体内化合物11即使在测试的最高剂量下，阿扑吗啡引起的攀爬，MK-801引起的活动过度和DOI引起的头部抽搐也没有明显的僵直。另外，它在CAR测试中表现出抑制作用。此外，在一个新颖的物体识别任务中，它显示了识别属性。因此，化合物11是有希望的候选多靶点抗精神病药。
• Pharmaceutical compositions and methods of treating hypertension
  申请人：John Wyeth & Brother Limited

  公开号：US04029801A1

  公开（公告）日：1977-06-14

  Pharmaceutical compositions containing a group of heterocyclic compounds and their use in treatment of disorders and diseases of the cardiovascular system and/or in the treatment of superficial and deep allergic phenomena is described. These compounds used in the composition and/or methods are piperidine compounds linked by the nitrogen atom to a substituted or unsubstituted cycloalkyl, aryl or heterocyclic radical through the intermediary of a group selected from a lower-alkylene radical, a monoketo lower-alkylene radical or a hydroxy-lower-alkylene radical, or a bivalent radical of the formula --NH.CO.(CH.sub.2).sub.n -- where n is 1, 2 or 3, ##STR1## or --0-(lower-alkylene)--. The piperidine ring is further substituted by an acylamino residue.

  本发明描述了含有杂环化合物组的药物组合物及其在治疗心血管系统疾病和/或治疗浅表和深层过敏现象中的应用。这些组合物和/或方法中使用的化合物是哌啶化合物，通过氮原子与取代或未取代的环烷基、芳基或杂环基团相连，中间通过一个选自低级烷叉基、单酮低级烷叉基或羟基低级烷叉基的基团，或一个二价基团，其公式为--NH.CO.(CH.sub.2).sub.n --，其中n为1、2或3，##STR1##或--O-(低级烷叉基)--。哌啶环进一步被酰胺基残基取代。
• Oxidative Cleavage of Epoxides with Ammonium Molybdate–H₂O₂System: An Efficient Route to α-Hydroxy Ketones
  作者：Nusrat Ismail、R. Nageswara Rao

  DOI：10.1246/cl.2000.844

  日期：2000.7

  Epoxides are efficiently converted into α-hydroxy ketones by employing ammonium molybdate–H2O2 system. The α-hydroxy ketones are prepared without the formation of α-hydroxy aldehydes, via 1,2-diols as intermediates. The products are formed with excellent yields under very mild conditions.

  环氧化物通过使用铵钼酸盐-H2O2体系高效转化为α-羟基酮。α-羟基酮的制备过程中不形成α-羟基醛，而是通过1,2-二醇作为中间体。所得到的产物在非常温和的条件下具有优异的产率。
• Aryloxypropanolaminotetralins, a process for their preparation and
  申请人：Elf Sanofi

  公开号：US05254595A1

  公开（公告）日：1993-10-19

  Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described. A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.

  具有β-阻断活性的芳氧基丙醇胺四氢萘，其通式为##STR1##，其中R为氢、羟基或甲氧基，Ar为可选择性取代的芳香或杂芳香基团，以光学活性或非活性形式及其酸加成盐被描述。它们的制备方法以及含有通式(i)化合物或其药学上可接受的酸加成盐的药物组合物也被描述。
• 1-Substituted-4-(2-oxo-1-imidazolidinyl) piperidines
  申请人：Ciba-Geigy Corporation

  公开号：US03956335A1

  公开（公告）日：1976-05-11

  Piperidines of the formula ##SPC1## In which R.sub.1 stands for optionally substituted aryl, R.sub.2 for hydrogen, lower alkyl, lower alkenyl, acyl or .alpha.-aryl-lower alkyl, R.sub.3 for a free or substituted hydroxyl group, alk for lower alkylene which separates the two nitrogen atoms by 2 or 3 carbon atoms, R.sub.4 represents hydrogen or lower alkyl and n represents an integer from 1 to 4, and their salts as well as processes for their manufacture and pharmaceutical compositions comprising such compounds, and a process for lowering the blood pressure wherein such compositions are administered to a warm-blooded host.

  式##SPC1##中的哌啶，其中R.sub.1代表可选择取代的芳基，R.sub.2代表氢、较低的烷基、较低的烯基、酰基或α-芳基-较低的烷基，R.sub.3代表自由或取代的羟基，alk代表通过2或3个碳原子分隔两个氮原子的较低的烷基，R.sub.4代表氢或较低的烷基，n代表从1到4的整数，以及它们的盐以及制造这些化合物的方法和包括这种化合物的制药组合物，以及一种降低血压的方法，其中将这种组合物给温血动物宿主。