(2S)-3-(4-acetamidophenoxy)-1,2-epoxypropane | 68051-01-4

• 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: (2S)-3-(4-acetamidophenoxy)-1,2-epoxypropane
• 英文别名: (S)-3-(4-acetamidophenoxy)-1,2-epoxypropane；(S)-glycidyl N-acetamidophenyl ether；(2S)-1-(4-acetylamino)phenoxy-2,3-epoxypropane；N-[4-[[(2S)-oxiran-2-yl]methoxy]phenyl]acetamide
• CAS: 68051-01-4
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: OQAKYHCGYGLHAZ-LLVKDONJSA-N

物化性质

• 沸点：
  423.4±20.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

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：
  0.36
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二氯苯乙胺 、 (2S)-3-(4-acetamidophenoxy)-1,2-epoxypropane 以 乙醇 为溶剂， 以83%的产率得到(S)-1-(4-acetamidophenoxy)-3-(3,4-dichlorophenylethylamino)-2-propanol
  参考文献：
  名称：

  Enantiomeric Propanolamines as selective N-Methyl-d-aspartate 2B Receptor Antagonists

  摘要：

  Enantiomeric propanolamines have been identified as a new class of NR2B-selective NMDA receptor antagonists. The most effective agents are biaryl structures, synthesized in six steps with overall yields ranging from 11-64%. The compounds are potent and selective inhibitors of NR2B-containing recombinant NMDA receptors with IC50 values between 30-100 nM. Potency is strongly controlled by substitution on both rings and the centrally located amine nitrogen. SAR analysis suggests that well-balanced polarity and chain-length factors provide the greatest inhibitory potency. Structural comparisons based on 3D shape analysis and electrostatic complementarity support this conclusion. The antagonists are neuroprotective in both in vitro and in vivo models of ischemic cell death. In addition, some compounds exhibit anticonvulsant properties. Unlike earlier generation NMDA receptor antagonists and some NR2B-selective antagonists, the present series of propanolamines does not cause increased locomotion in rodents. Thus, the NR2B-selective antagonists exhibit a range of therapeutically interesting properties.

  DOI：

  10.1021/jm8002153
• 作为产物：
  描述：

  对乙酰氨基酚 在 K₂Fe(CN)6 ruthenium trichloride 、 sodium periodate 、 四氧化锇 、 氯化亚砜 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 22.0h， 生成 (2S)-3-(4-acetamidophenoxy)-1,2-epoxypropane
  参考文献：
  名称：

  通过OsO 4催化的不对称二羟基化反应不对称合成芳氧基丙醇胺

  摘要：

  描述了一种简单有效的方法，该方法包括对映异构体合成首个不对称合成西酞洛尔的β-肾上腺素能阻断剂。关键步骤是（i）芳基烯丙基醚无尖锐的不对称二羟基化反应，以将手性引入分子中；以及（ii）使用三步法将环状硫酸盐转化为相应的环氧化物。

  DOI：

  10.1016/j.tet.2005.01.074

文献信息

• Propanolamine derivatives
  申请人：Fujisawa Pharmaceutical Co. Ltd.

  公开号：US20020120148A1

  公开（公告）日：2002-08-29

  This invention relates to new propanolamine derivatives or salts thereof represented by the following formula [I]: 1 Wherein each symbol is as defined in the specification or salts thereof which have gut selective sympathomimetic, anti-ulcerous, anti-pancreatitis, lipolytic, anti-urinary incontinence and anti-pollakiuria activities, to processes for the preparation thereof, to a pharmaceutical composition comprising the same and to a method for the prevention and/or treatment diseases indicated in the specification to a human being or an animal.

  这项发明涉及新的丙醇胺衍生物或其盐，其化学式如下所示：1其中每个符号如规范中定义，或具有选择性肠道交感神经兴奋作用、抗溃疡、抗胰腺炎、脂解作用、抗尿失禁和抗尿频活性的盐，以及其制备方法、包含相同的药物组合物以及用于预防和/或治疗规范中指示的疾病的方法，适用于人类或动物。
• Synthesis and .beta.-adrenergic antagonist activity of stereoisomeric practolol and propranolol derivatives
  作者：Katerina Leftheris、Murray Goodman

  DOI：10.1021/jm00163a036

  日期：1990.1

  synthesized in which the N-isopropyl group of the drug was replaced by an asymmetric heptanoic acid terminated by a substituted p-toluidide or p-(trifluoromethyl)anilide. The asymmetric epoxide, 3-(p-acetamidophenoxy)-1,2-epoxypropane, was allowed to react with a preformed enantiomeric 6-aminoheptanoic acid amide to yield the stereoisomeric practolol congener derivatives. An asymmetric drug precursor epoxide

  已经合成了一系列立体异构的普克洛尔和普萘洛尔衍生物，其中药物的N-异丙基被不对称的庚酸代替，庚酸的末端是取代的对甲苯胺或对-（三氟甲基）苯胺。使不对称环氧化物3-（对乙酰氨基苯氧基）-1，2-环氧丙烷与预先形成的对映异构体6-氨基庚酸酰胺反应，以产生立体异构的蝶甾醇同类衍生物。由对乙酰氨基苯酚制备不对称药物前体环氧化物，并使对映体3-（甲苯磺酰氧基）-1,2-环氧丙烷6-氨基庚酸酰胺与3-（1-萘氧基）-1,2之一对映体反应-环氧丙烷。该药物前体环氧化合物是通过将1-萘酚与对映体3-（甲苯磺酰氧基）-1结合制备的，2-环氧丙烷（Sharpless环氧）或通过将1-萘酚与对映异构体3-（甲苯磺酰氧基）-1，2-丙二醇结合，然后进行环氧化。对Practolol衍生物进行的药理研究表明，增强的效力和组织/亚受体特异性对药物不对称碳的构型和间隔基不对称碳的构型有很大的依赖性。与其他立体异构同类物衍
• Use of beta 3 adrenergic receptor agonists in the treatment of dysuria
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP1382333A2

  公开（公告）日：2004-01-21

  The application relates to the use of a β3 adrenergic receptor agonist selected from the group consisting of formulas (IV),(V),(VI),(VII) and (VIII) for the manufacture of a medicament for the prophylactic and/or the therapeutic treatment of dysuria. In the above formulae, the various groups, substituents and variables have the meanings given in the description.

  本申请涉及选自式(IV)、(V)、(VI)、(VII)和(VIII)组成的组中的β3 肾上腺素能受体激动剂的用途。 用于制造预防和/或治疗排尿困难的药物。在上式中，各基团、取代基和变量具有说明中给出的含义。
• Enantioselective ring opening of epoxides with trimethylsilyl azide (TMSN3) in the presence of β-cyclodextrin: an efficient route to 1,2-azido alcohols
  作者：Ahmed Kamal、M Arifuddin、Maddamsetty V Rao

  DOI：10.1016/s0957-4166(99)00464-4

  日期：1999.11

  The ring opening of epoxides with nucleophiles such as TMSN3 and isopropylamine takes place enantioselectively in the presence of (beta-cyclodextrin under extremely mild conditions and the azido alcohols and amino alcohols are formed as (S)-isomers. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Determination of the enantiomeric purity and the configuration of β-aminoalcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR: application to β-blockers
  作者：Marcel Apparu、Younes Ben Tiba、Pierre-Marc Léo、Sylvain Hamman、Christian Coulombeau

  DOI：10.1016/s0957-4166(00)00254-8

  日期：2000.7

  A method has been developed for determining the enantiomeric purity and the absolute configuration of beta-aminoalcohols of type ArOCH2CH(OH)CH2NHR (R = iPr, tBu). To determine enantiomeric purity, the amine function was first protected by a benzyl group, then the compound formed was esterified using the acid chloride of (R)-2-fluorophenylacetic acid (AFPA). The F-19 NMR analysis of the derivative obtained revealed the presence of two distinctly separate signals (similar to 2.5 ppm), the one for the RS-SR pair being the most deshielded. The configuration was determined directly on the aminoalcohol by using the acid. In stoichiometric conditions, when R = iPr, the amide function was obtained very preponderantly. The F-19 NMR spectrum of the amide presented four distinct signals when derivatization was carried out by means of a reaction between the (+/-)-beta-aminoalcohol and the (R)-AFPA. The extreme signals, which were over 3.5 ppm apart, did not belong to the same diastereomer. With R = tBu essentially the ester function was obtained. The first studies revealed the presence of two signals, though not as clearly separated as in the previous cases. Each experiment was simple to perform, and purification was not necessary. Mosher's acid gave unsatisfactory results in each case. (C) 2000 Elsevier Science Ltd. All rights reserved.