(S)-4-benzyloxy-3-nitrostyrene oxide | 188730-96-3

• 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: (S)-4-benzyloxy-3-nitrostyrene oxide
• 英文别名: (2S)-2-(3-nitro-4-phenylmethoxyphenyl)oxirane
• CAS: 188730-96-3
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: MOGUBMMGIJLRHQ-OAHLLOKOSA-N

物化性质

• 沸点：
  438.5±45.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyloxy-3-nitrostyrene oxide 在 platinum(IV) oxide 氢气 作用下， 生成 CM4Wfy22FU
  参考文献：
  名称：

  Enantio- and diastereoselective synthesis of all four stereoisomers of formoterol

  摘要：

  Enantioselective syntheses of all four stereoisomers of formoterol are accomplished using asymmetric catalytic borane reductions with chiral oxazaborolidines as reducing agents. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00088-9
• 作为产物：
  描述：

  3'-硝基-4'-苄氧基-2-溴苯乙酮 在 硼烷四氢呋喃络合物 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 74.5h， 生成 (S)-4-benzyloxy-3-nitrostyrene oxide
  参考文献：
  名称：

  An efficient enantioselective synthesis of (R,R)-formoterol, a potent bronchodilator, using lipases

  摘要：

  0The potent beta(2)-adrenergic receptor agonist formoterol (R,R)-1 has been obtained in enantiomerically pure form by a convenient chemoenzymatic approach by coupling of epoxide (R)-6 with the unprotected primary amine (R)-9. Both chiral precursors have been prepared by enantiodifferentiation processes involving Pseudomonas cepacia (lipase PS) and Candida antarctica lipase (CALB), respectively. For the resolution of amine 9, we have found that utilization of triethylamine as non-reactive base enhances the reaction rate and the enantioselectivity of the process. The key coupling reaction of (R)-6 and (R)-9 has been conducted through derivatization of the amine with the labile trimethylsilyl group, which liberates the amino group of the resulting amino alcohol (R,R)-11 upon column chromatography purification. In this way, the overall approach is shorter than others previously described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00238-x

文献信息

• Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Hydrophobic Metal−Amido Complexes in Aqueous Micelles and Vesicles
  作者：Fei Wang、Hui Liu、Linfeng Cun、Jin Zhu、Jingen Deng、Yaozhong Jiang

  DOI：10.1021/jo0514826

  日期：2005.11.1

  Asymmetric transfer hydrogenation of ketones, especially (X-bromomethyl aromatic ketones, catalyzed by unmodified, hydrophobic transition metal-amido complexes (TsDPEN-M), was performed successfully with significant enhancement of activity, chemoselectivity, and enantioselectivity (up to 99% ee) in aqueous media containing micelles and vesicles. The hydrophobic catalyst, embedded in micelles constructed from the surfactant cetyltrimethylammonium bromide (CTAB), could be separated from the organic phase along with the products and was recycled for at least six times.
• AMINOALCOHOL DERIVATIVES USEFUL FOR THE TREATMENT OF GASTROINTESTINAL DISORDERS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP1230210A1

  公开（公告）日：2002-08-14
• [EN] AMINOALCOHOL DERIVATIVES USEFUL FOR THE TREATMENT OF GASTROINTESTINAL DISORDERS<br/>[FR] DÉRIVÉS D'AMINO ALCOOLS UTILES POUR LE TRAITEMENT DE TROUBLES GASTRO-INTESTINAUX
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2001036375A1

  公开（公告）日：2001-05-25

  This invention relates to new aminoalcohol derivatives or salts thereof represented by formula (I): 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.