(S)-1-(3-氯苯基)-2-羟基-1-丙酮 | 287477-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)-1-(3-氯苯基)-2-羟基-1-丙酮
• 英文名称: (S)-1-(3-chlorophenyl)-2-hydroxypropan-1-one
• 英文别名: (S)-1-(3-Chlorophenyl)-2-hydroxypropanone；(S)-3'-chloro-2-hydroxypropiophenone；(S)-3'-chloro-2-hydroxyl-propiophenone；(S)-1-(3-Chlorophenyl)-2-hydroxy-1-propanone；(2S)-1-(3-chlorophenyl)-2-hydroxypropan-1-one
• CAS: 287477-53-6
• 化学式: C₉H₉ClO₂
• 分子量: 184.622
• InChiKey: PRVHLTNNKRCHGO-LURJTMIESA-N

物化性质

• 溶解度：
  可溶于氯仿、二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(3-氯苯基)-2-羟基-1-丙酮 在 lutidine 作用下， 以 二氯甲烷 为溶剂， 生成 (R,R)-羟基安非他酮
  参考文献：
  名称：

  Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate

  摘要：

  A stereospecific method for the synthesis of enantiopure alpha -aminoketone from its corresponding alpha -hydroxy-ketone via the triflate intermediate is discussed. This strategy provides a rapid and efficient route for the preparation of either enantiomer of bupropion and its biologically active hydroxylated metabolite, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00349-9
• 作为产物：
  描述：

  tert-butyldimethyl[1-(3-chlorophenyl)prop-1-enyloxy]silane 在 AD-mix-α 、 水 作用下， 以 叔丁醇 为溶剂， 以82%的产率得到(S)-1-(3-氯苯基)-2-羟基-1-丙酮
  参考文献：
  名称：

  Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate

  摘要：

  A stereospecific method for the synthesis of enantiopure alpha -aminoketone from its corresponding alpha -hydroxy-ketone via the triflate intermediate is discussed. This strategy provides a rapid and efficient route for the preparation of either enantiomer of bupropion and its biologically active hydroxylated metabolite, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00349-9

文献信息

• Continuous enzymatic stirred tank reactor cascade with unconventional medium yielding high concentrations of (<i>S</i>)-2-hydroxyphenyl propanone and its derivatives
  作者：Reinhard Oeggl、Juliane Glaser、Eric von Lieres、Dörte Rother

  DOI：10.1039/d0cy01666g

  日期：——

  of >99%. Further, the substrate range of the applied catalyst Pseudomonas putida benzoylformate decarboxylase variant L461A was analysed. This revealed numerous halogenated, methoxylated and nitro-derivatives in ortho, meta, and para position, which can in principle be gained by the established process. As an example, the applied cSTR concept was transferred to p-methoxy benzaldehyde with good results

  生物催化在流动化学中的实施提供了符合绿色化学原理的协同合成优势。然而，在许多情况下，高底物浓度的转化受到不溶性问题或底物毒性的阻碍。在这里，已经建立了在基于甲基叔丁基醚的有机反应环境中，即微水反应体系中，由廉价的苯甲醛和乙醛连续合成 ( S )-2-羟基苯基丙酮 (2-HPP) 。确定应用的全细胞催化剂的动力学参数以设计用于（S)-2-HPP 合成。这揭示了在空间坐标上分布乙醛以保持低于毒性浓度阈值的必要性。因此，三个连续搅拌釜反应器 (cSTR) 在技术级联中结合，每个单元都有额外的乙醛流入。基于质量平衡和动力学模型描述了该反应装置的催化行为。酶失活由一个新的分阶段模型描述，并与一个简单的通用模型进行比较。优化的连续设置在 8 小时内产生了 190 mM ( S )-HPP，ee > 98%。产物很容易通过结晶从有机反应环境中回收，分离产率为 68%，纯度 >99%。此外，应用催化剂恶臭
• [EN] BUPROPION METABOLITES AND METHODS OF THEIR SYNTHESIS AND USE<br/>[FR] METABOLITES DU BUPROPION ET LEURS PROCEDES DE SYNTHESE ET D'UTILISATION
  申请人：SEPRACOR INC

  公开号：WO2001062257A2

  公开（公告）日：2001-08-30

  Methods and compositions are disclosed which utilize metabolites of bupropion for treating disorders ameliorated by inhibition of neuronal monoamine reuptake. Such disorders include, but are not limited to, sexual dysfunction, affective disorders, cerebral function disorders, cigarette smoking, and incontinence. Methods of making optically pure bupropion metabolites are also disclosed.

  本发明公开了利用丁丙腈代谢物治疗神经元单胺再摄取抑制改善的疾病的方法和组合物。这些疾病包括但不限于性功能障碍、情感障碍、脑功能障碍、吸烟和失禁。本发明还公开了制备光学纯丁丙腈代谢物的方法。
• Bupropion metabolites and methods of their synthesis and use
  申请人：SEPRACOR INC.

  公开号：US20020052341A1

  公开（公告）日：2002-05-02

  Methods and compositions are disclosed which utilize metabolites of bupropion for treating disorders ameliorated by inhibition of neuronal monoamine reuptake. Such disorders include, but are not limited to, sexual dysfunction, affective disorders, cerebral function disorders, cigarette smoking, and incontinence. Methods of making optically pure bupropion metabolites are also disclosed.

  本文披露了利用伯泊隆代谢物治疗神经元单胺重摄取抑制所改善的疾病的方法和组合物。这些疾病包括但不限于性功能障碍、情感障碍、脑功能障碍、吸烟和失禁。本文还披露了制备光学纯伯泊隆代谢物的方法。
• Intermediates of bupropion metabolites synthesis
  申请人：Fang Qun Kevin

  公开号：US20060058300A1

  公开（公告）日：2006-03-16

  Methods and compositions are disclosed which utilize metabolites of bupropion for treating disorders ameliorated by inhibition of neuronal monoamine reuptake. Such disorders include, but are not limited to, sexual dysfunction, affective disorders, cerebral function disorders, cigarette smoking, and incontinence. Methods of making optically pure bupropion metabolites are also disclosed.

  本文公开了利用伯泊隆代谢产物治疗通过抑制神经元单胺再摄取改善的疾病的方法和组合物。这些疾病包括但不限于性功能障碍，情感障碍，脑功能障碍，吸烟和失禁。本文还公开了制备光学纯伯泊隆代谢产物的方法。
• Bupropion metabolites and methods of use
  申请人：Sepracor, Inc.

  公开号：US06337328B1

  公开（公告）日：2002-01-08

  Methods are disclosed which utilize metabolites of bupropion for treating sexual dysfunction.

  本发明揭示了利用伯普利定代谢产物治疗性功能障碍的方法。