(S)-3-(4-iodophenoxy)-1,2-epoxypropane | 256372-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-3-(4-iodophenoxy)-1,2-epoxypropane
• 英文别名: (2S)-2-[(4-iodophenoxy)methyl]oxirane；(S)-glycidyl 4-iodo-phenyl ether
• CAS: 256372-55-1
• 化学式: C₉H₉IO₂
• 分子量: 276.074
• InChiKey: KOMIXVZMMDGHND-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-iodophenoxy)-1,2-epoxypropane 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， 生成 (R)-Fluoro-phenyl-acetic acid (S)-2-(benzyl-isopropyl-amino)-1-(4-iodo-phenoxymethyl)-ethyl ester
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)00254-8
• 作为产物：
  描述：

  4-碘苯酚 、 (S)-(+)-对甲苯磺酸缩水甘油酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到(S)-3-(4-iodophenoxy)-1,2-epoxypropane
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)00254-8

文献信息

• [EN] NOVEL IMIDAZOLE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'IMIDAZOLE
  申请人：TAISHO PHARMA CO LTD

  公开号：WO2018216822A1

  公开（公告）日：2018-11-29

  Provided are novel compounds represented by the following general formula [1] or pharmaceutically acceptable salts thereof, that inhibit LpxC, as well as pharmaceutical drugs comprising those compounds or pharmaceutically acceptable salts thereof, that exhibit antimicrobial activity against gram-negative bacteria including multi-drug resistant strains and that are useful in the treatment of bacterial infections.

  提供了由以下一般式[1]表示的新化合物或其药用盐，其抑制LpxC，以及包含这些化合物或其药用盐的药物，对革兰氏阴性细菌包括多药耐药菌株表现出抗微生物活性，并且在治疗细菌感染中有用。
• Use of 5HT-1F receptor antagonists for treating anxiety disorders
  申请人：ELI LILLY AND COMPANY

  公开号：EP0976747A3

  公开（公告）日：2000-09-13

  The present invention provides a method for the treatment of prevention of anxiety disorders which comprises administering to a mammal in need of such treatment a serotonin 5-HT1F receptor antagonist.

  本发明提供了一种治疗预防焦虑症的方法，包括向需要此类治疗的哺乳动物施用一种5-HT1F受体拮抗剂。
• 5-HT1F antagonists
  申请人：Eli Lilly and Company

  公开号：US06242450B1

  公开（公告）日：2001-06-05

  This invention provides 5-HT1f antagonists of Formula I: where AR1, AR2, R, and R′ are as defined in the specification.

  这项发明提供了化学式I中的5-HT1f拮抗剂：其中AR1、AR2、R和R'如规范中所定义。
• US6242450B1
  申请人：——

  公开号：US6242450B1

  公开（公告）日：2001-06-05
• [EN] TREATMENT OF ANXIETY DISORDERS<br/>[FR] TRAITEMENT DES TROUBLES ANXIEUX
  申请人：LILLY CO ELI

  公开号：WO2000006082A2

  公开（公告）日：2000-02-10

  The present invention provides a method for the treatment or prevention of anxiety disorders which comprises administering to a mammal in need of such treatment a serotonin 5-HT1F receptor antagonist.