(R)-2-(tert-butylamino)-1-[3,5-bis(dimethylcarbamoyloxy)phenyl]ethanol | 788821-30-7

• 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: (R)-2-(tert-butylamino)-1-[3,5-bis(dimethylcarbamoyloxy)phenyl]ethanol
• 英文别名: (R)-bambuterol；R-bambuterol；bambuterol；[3-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-5-(dimethylcarbamoyloxy)phenyl] N,N-dimethylcarbamate
• CAS: 788821-30-7
• 化学式: C₁₈H₂₉N₃O₅
• 分子量: 367.445
• InChiKey: ANZXOIAKUNOVQU-HNNXBMFYSA-N

物化性质

• 沸点：
  500.9±50.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  91.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-二乙酰氧基苯乙酮 在 溴 、 potassium carbonate 、 sodium chloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 异丙醇 、 甘油 、 乙腈 为溶剂， 反应 158.34h， 生成 (R)-2-(tert-butylamino)-1-[3,5-bis(dimethylcarbamoyloxy)phenyl]ethanol
  参考文献：
  名称：

  Synthesis of (R)-bambuterol based on asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with incubated whole cells of Williopsis californica JCM 3600

  摘要：

  To achieve the synthesis of (R)-bambuterol, a prodrug of (R)-terbutaline, asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with whole cells of Williopsis californica JCM 3600 pre-incubated on glycerol as a carbon source was examined. Initially, the insolubility of this crystalline substrate (mp 126-127 degrees C) in the incubation broth was an obstacle that needed to be overcome. To solve the problem, the concentration of glycerol was increased to 10% during reduction. Glycerol worked well for recycling oxido-reduction cofactors and for enhancing the water solubility of the substrate. The reduction proceeded smoothly to give enantiomerically pure (R)-alcohol in 81% isolated yield. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.08.003

文献信息

• Bronchospasmolytic carbamate derivatives
  申请人：Aktiebolaget Draco

  公开号：US04419364A1

  公开（公告）日：1983-12-06

  New bronchospasmolytically active compounds exhibiting long duration of action and reduced undesired side effects of the structural formula ##STR1## and therapeutically acceptable salts thereof, in which formula R is selected from the group consisting of --C(CH.sub.3).sub.3, ##STR2## R.sup.1 is selected from the group consisting of H and R.sup.2, R.sup.2 represents the radical of the formula ##STR3## wherein R.sup.3 is selected from the group consisting of (a) H (b) alkyl groups containing 1-3 carbon atoms ##STR4## wherein R.sup.5 is selected from the group consisting of (e) OH (b) alkoxy groups containing 1-3 carbon atoms and wherein R.sup.4 is selected from the group consisting of (a) H (b) alkyl groups containing 1-3 carbon atoms, with the proviso that R.sup.3 and R.sup.4 are combined as follows: ______________________________________ when R.sup.3 is then is R.sup.4 ______________________________________ H H alkyl group of 1-3 carbon atoms H or an alkyl group of 1-3 carbon atoms ##STR5## H ______________________________________ PA1 processes for the preparation thereof, chemical intermediates at their preparation, pharmaceutical preparations containing them, and their medicinal use.

  新的支气管痉挛解除活性化合物，展现出长效作用和减少不良副作用，其结构式为##STR1##和其医疗可接受的盐，其中R选择自--C(CH.sub.3).sub.3，##STR2##R.sup.1选择自H和R.sup.2，R.sup.2代表式的基团##STR3##其中R.sup.3选择自(a)H(b)含有1-3个碳原子的烷基基团##STR4##其中R.sup.5选择自(e)OH(b)含有1-3个碳原子的烷氧基团，R.sup.4选择自(a)H(b)含有1-3个碳原子的烷基基团，但须满足以下条件：当R.sup.3为时，则为R.sup.4；当R.sup.3为H或含有1-3个碳原子的烷基基团时，则为H。PA1为其制备过程，化学中间体及其制备，含有它们的制药制剂，以及它们的药用。
• US7495028B2
  申请人：——

  公开号：US7495028B2

  公开（公告）日：2009-02-24
• Synthesis of (R)-bambuterol based on asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with incubated whole cells of Williopsis californica JCM 3600
  作者：Kento Asami、Takuya Machida、Sonna Jung、Kengo Hanaya、Mitsuru Shoji、Takeshi Sugai

  DOI：10.1016/j.molcatb.2013.08.003

  日期：2013.12

  To achieve the synthesis of (R)-bambuterol, a prodrug of (R)-terbutaline, asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with whole cells of Williopsis californica JCM 3600 pre-incubated on glycerol as a carbon source was examined. Initially, the insolubility of this crystalline substrate (mp 126-127 degrees C) in the incubation broth was an obstacle that needed to be overcome. To solve the problem, the concentration of glycerol was increased to 10% during reduction. Glycerol worked well for recycling oxido-reduction cofactors and for enhancing the water solubility of the substrate. The reduction proceeded smoothly to give enantiomerically pure (R)-alcohol in 81% isolated yield. (C) 2013 Elsevier B.V. All rights reserved.