1-(3-羟基苯基)-2-(甲基氨基)乙酮 | 52093-42-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-羟基苯基)-2-(甲基氨基)乙酮
• 英文名称: Neosynephrine ketone
• 英文别名: 1-(3-hydroxyphenyl)-2-(methylamino)ethanone；phenylephrine；1-(3-hydroxy-phenyl)-2-methylamino-ethanone；1-(3-Hydroxy-phenyl)-2-methylamino-aethanon
• CAS: 52093-42-2
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: BDLRAEZKFVYJPW-UHFFFAOYSA-N

物化性质

• 熔点：
  135°C
• 稳定性/保质期：
  <p>遵照规定使用和储存，则不会分解。</p>

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922509090
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。最好存放在阴凉、干燥的地方。

反应信息

• 作为反应物：
  描述：

  1-(3-羟基苯基)-2-(甲基氨基)乙酮 在 葡萄糖 、 potassium chloride 、 氯化铵 作用下， 以81%的产率得到L-去氧肾上腺素
  参考文献：
  名称：

  Enantioselective synthesis of (S)-phenylephrine by whole cells of recombinant Escherichia coli expressing the amino alcohol dehydrogenase gene from Rhodococcus erythropolis BCRC 10909

  摘要：

  (R)-phenylephrine [(R)-PE] is an alpha(1)-adrenergic receptor agonist that is widely used in over-the-counter drugs to treat the common cold. We found that Rhodococcus erythropolis BCRC 10909 can convert detectable level of 1-(3-hydroxyphenyl)-2-(methylamino) ethanone (HPMAE) to (S)-PE by high performance liquid chromatography tandem mass spectrometry analysis. An amino alcohol dehydrogenase gene (RE_AADH) which possesses the ability to convert HPMAE to (S)-PE was then isolated from R. erythropolis BCRC 10909 and expressed in Escherichia coli NovaBlue. The purified RE_AADH, tagged with 6x His, had a molecular mass of approximately 30 kDa and exhibited a specific activity of 0.19 mu U/mg to HPMAE in the presence of NADPH, indicating this enzyme could be categorized as NADP(+)-dependent short-chain dehydrogenase reductase. E. coli NovaBlue cell expressing the RE_AADH gene was able to convert HPMAE to (S)-PE with more than 99% enantiomeric excess (ee), 78% yield and a productivity of 3.9 mmol (S)-PE/L h in 12 h at 30 degrees C and pH 7. The (S)-PE, recovered from reaction mixture by precipitation at pH 11.3, could be converted to (R)-PE (ee >99%) by Walden inversion reaction. This is the first reported biocatalytic process for the production of (S)-PE from HPMAE. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.procbio.2010.06.003
• 作为产物：
  描述：

  去氧肾上腺素碱 在 (R)-epinephrine dehydrogenase 、 还原型辅酶Ⅰ 作用下， 以 aq. phosphate buffer 为溶剂， 生成 1-(3-羟基苯基)-2-(甲基氨基)乙酮
  参考文献：
  名称：

  Purification and characterization of a novel carbonyl reductase involved in oxidoreduction of aromatic β-amino ketones/alcohols

  摘要：

  Aromatic beta-amino ketones/alcohols such as adrenalone play an important role in some stereoselective synthesis of pharmaceuticals. Unfortunately, the transformation of aromatic beta-amino ketones to their chiral alcohols has been carried out chemically as no corresponding biocatalyst has been available. Here, a novel carbonyl reductase responsible for the reduction of adrenalone to (R)-(-)-epinephrine was identified and characterized from Kocuria rhizophila. This enzyme was purified to homogeneity by ammonium sulfate precipitation followed by ion-exchange column chromatography, hydrophobic chromatography and gel chromatography. The purified enzyme yielded pure (R)-enantiomer product with high activity and utilized NADH as the cofactor. The enzyme had special significance by showing selectivity for many aromatic beta-amino ketones/alcohols such as 2-amino-acetophenone, 2-amino-4'-hydroxyacetophenone, isoproterenol and ephedrine. The maximum reaction rate (V-max) and apparent Michaelis-Menten constant (K-m) for adrenalone and NADH were 14.62 mu mol/(min mg) protein and 0.189 mM, 11.66 mu mol/(min mg) protein and 0.204 mM respectively. These properties ensure the enzyme a promising future for industrial application as a replacement of chemical synthesis of aromatic beta-amino chiral alcohols. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.procbio.2014.03.023

文献信息

• [EN] PYRIMIDINE DERIVATIVES AS OREXIN RECEPTORS ANTAGONISTS<br/>[FR] DERIVES DE PYRIMIDINE UTILISES EN TANT QU'ANTAGONISTES DE RECEPTEURS D'OREXINE
  申请人：SANOFI AVENTIS

  公开号：WO2005075458A1

  公开（公告）日：2005-08-18

  The present invention relates to the orexin receptor antagonists of the general formula (I), which are selective to orexin I receptors. (I) -wherein Ar stands for phenyl group or a 5- or 6-membered heterocyclic ring containing 1-3 identical or different heteroatoms or methylenedioxyphenyl group -these groups may optionally be substituted with one or more identical or different C1.4 alkyl group, halogen atom, hydroxyl group, C1-4 alkoxy group, trihalogenomethyl group, NHC1.4 alkyl, -N(CI-4 alkyl)2 or -NHC(=0)-C1-4 alkyl group,

  本发明涉及通式（I）的俄利新受体拮抗剂，这些拮抗剂对俄利新I受体具有选择性。其中，Ar代表苯基或含有1-3个相同或不同杂原子或亚甲二氧基苯基的5-或6元杂环的环，这些基团可以选择性地用一个或多个相同或不同的C1.4烷基基团、卤原子、羟基、C1-4烷氧基、三卤甲基基团、NHC1.4烷基、-N(CI-4烷基)2或-NHC(=0)-C1-4烷基基团取代。
• [EN] SYNTHESIS OF ENANTIOMERICALLY PURE 2-HYDROXY-2-ARYL-ETHYLAMINES<br/>[FR] SYNTHÈSE DE 2-HYDROXY-2-ARYL-ÉTHYLAMINES ÉNANTIOMÉRIQUEMENT PURES
  申请人：CAMBREX CHARLES CITY INC

  公开号：WO2009086283A1

  公开（公告）日：2009-07-09

  The present invention relates to an improved process for preparing enantiomerically pure 2-hydroxy-2-aryl-ethylamines, and their pharmaceutically acceptable salts, by transition metal catalyzed asymmetric hydrogenation preferably using a ruthenium transition metal catalyst system having as a chiral, bidentate phosphine ligand ((R)-I -diphenylphosphino-2- [(S)-α-(N,N-dimethylamino)-o-diphenylphosphinophenyl)methyl] ferrocene), such as Chiralyst LM 1010 RS available from Umicore AG & Co., KG.

  本发明涉及一种改进的制备对映纯2-羟基-2-芳基乙基胺及其药学可接受盐的方法，通过过渡金属催化不对称氢化，优选使用具有手性双齿膦配体的钌过渡金属催化剂体系（例如Chiralyst LM 1010 RS，由Umicore AG＆Co. KG提供），该配体为((R)-I-二苯基膦酸-2- [（S）-α-（N，N-二甲基氨基）-o-二苯基膦酸苯基甲基]二茂铁）。
• PYRIMIDINE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
  申请人：ARANYI Peter

  公开号：US20070043037A1

  公开（公告）日：2007-02-22

  The present invention relates to the orexin receptor antagonists of the general formula (I), which are selective to orexin I receptors.

  本发明涉及通式（I）的促进素受体拮抗剂，其对促进素I受体具有选择性。
• Ketoreductases
  申请人：C-LEcta GmbH

  公开号：US10093905B2

  公开（公告）日：2018-10-09

  The invention relates to ketoreductases and the use thereof. The ketoreductases of the invention are particularly useful for enzymatically catalyzing the reduction of ketones to chiral secondary alcohols.

  本发明涉及酮还原酶及其用途。本发明的酮还原酶特别适用于酶催化酮还原成手性仲醇。
• Ketoreductase polypeptides for the preparation of phenylephrine
  申请人：Codexis, Inc.

  公开号：US10358631B2

  公开（公告）日：2019-07-23

  The disclosure relates to engineered ketoreductase polypeptides and processes of using the polypeptides for production of phenylephrine.

  本公开涉及工程酮还原酶多肽和使用该多肽生产苯肾上腺素的工艺。