(S)-2-bromo-1-(3-nitrophenyl)ethanol

• 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)-2-bromo-1-(3-nitrophenyl)ethanol
• 英文别名: (1S)-2-bromo-1-(3-nitrophenyl)ethanol
• 化学式: C₈H₈BrNO₃
• 分子量: 246.06
• InChiKey: GGHMLSGJPIBJRA-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-3'-硝基苯乙酮 在 [RhCl2(p-cymene)]2 、 (R,R,R)-N-camphorsulfonyl-diphenylethylene diamine 、 sodium formate 、 sodium dodecyl-sulfate 作用下， 以 水 为溶剂， 反应 8.0h， 以85%的产率得到(S)-2-bromo-1-(3-nitrophenyl)ethanol
  参考文献：
  名称：

  The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol

  摘要：

  The asymmetric transfer hydrogenation of a series of halo-substituted aryl methyl ketones, including those substituted in both alpha-methyl and aryl rings, was studied for the preparation of chiral halohydrins. Up to 99.7% ee was obtained with 2-chloro-1-(2-chlorophenyl)ethanone as the substrate and Ru-CsDPEN as the catalyst in an HCOONa/H2O system. (R)-Clorprenaline, a drug used in the treatment of respiratory disorders, such as bronchitis and asthma, and (S)-sotalol, a class-III antiarrhythmic compound, were prepared with these chiral halohydrins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.017

文献信息

• Selective Asymmetric Transfer Hydrogenation of α-Substituted Acetophenones with Bifunctional Oxo-Tethered Ruthenium(II) Catalysts
  作者：Yamato Yuki、Taichiro Touge、Hideki Nara、Kazuhiko Matsumura、Mitsuhiko Fujiwhara、Yoshihito Kayaki、Takao Ikariya

  DOI：10.1002/adsc.201701227

  日期：2018.2.1

  A practical method for the asymmetric transfer hydrogenation of α‐substituted ketones was developed utilizing oxo‐tethered N‐sulfonyldiamine‐ruthenium complexes. Reduction by HCO2H and HCO2K in a mixed solvent of EtOAc/H2O allowed for the selective synthesis of halohydrins from 2‐bromoacetophenone (98%) and 2‐chloroacetophenone (>99%), leading to suppressed undesired side reactions stemming from formylation

  利用氧连接的N-磺酰基二胺-钌络合物开发了一种实用的方法，用于α-取代酮的不对称转移加氢。在EtOAc / H 2 O混合溶剂中通过HCO 2 H和HCO 2 K还原，可以从2-溴苯乙酮（98％）和2-氯苯乙酮（> 99％）选择性合成卤代醇，从而抑制了不良的副反应在典型的反应条件下，使用HCO 2 H和Et 3的5：2共沸混合物，从甲酰化反应中提取N.一系列功能基团（如卤素，甲氧基，硝基，二甲基氨基和酯基）的耐受性良好，凸显了该方法的潜力。即使底物/催化剂（S / C）为5000，也能保持接近完全的选择性和较好的ee。这种催化剂体系对于不对称地还原α-磺化酮也有效，而不会侵蚀离去基团。
• Novel tricyclic compounds and drug compositions containing same
  申请人：ASAHI KASEI KOGYO KABUSHIKI KAISHA

  公开号：US20030139475A1

  公开（公告）日：2003-07-24

  Compounds having a &bgr;-3 adrenaline receptor agonist and are useful as drugs for the treatment and prevention of diabetes, obesity, hyperlipemia, etc., represented by a general formula (I) and salts thereof, and a process for producing these, and their intermediates, wherein R represents hydrogen or methyl; R 1 represents hydrogen, halogen, hydroxy, benzyloxy, amino, or hydroxymethyl; R 2 represents hydrogen, hydroxymethyl, NHR 3 , SO 2 NR 4 R 4′ , or nitro; R 6 represents hydrogen or lower alkyl; and X represents nitrogen, R 9 represents hydrogen, one of R 7 and R 8 represent hydrogen, and the other thereof represents hydrogen, amino, acetylamino, or hydroxy.

  具有&bgr;-3肾上腺素受体激动剂的化合物，可用于治疗和预防糖尿病、肥胖症、高脂血症等疾病，其通式表示为(I)，并且包括其盐，以及制备这些化合物和其中间体的方法。其中，R代表氢或甲基；R1代表氢、卤素、羟基、苄氧基、氨基或羟甲基；R2代表氢、羟甲基、NHR3、SO2NR4R4′或硝基；R6代表氢或低碳基；X代表氮；R9代表氢；R7和R8中的一个代表氢，而另一个代表氢、氨基、乙酰氨基或羟基。
• NOVEL TRICYCLIC COMPOUNDS AND DRUG COMPOSITIONS CONTAINING THE SAME
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0882707A1

  公开（公告）日：1998-12-09

  Compounds represented by general formula (I) or salts thereof, a process for producing the same, and intermediates therefor, wherein R represents hydrogen or methyl; R1 represents hydrogen, hologeno, hydroxy, benzyloxy, amino, or hydroxymethyl; R2 represents hydrogen, hydroxymethyl, NHR3, SO2NR4R4, or nitro; R6 represents hydrogen or lower alkyl; and X represents nitrogen, oxygen, sulfur, or methylene, provided that when X represents nitrogen, oxygen, or sulfur, then R9 represents hydrogen, one of R7 an R8 represents hydrogen, and the other thereof represents hydrogen, amino, acetylamino, or hydroxy, and when X represents methylene, then R7 and R8 each represents hydrogen and R9 represents hydrogen, amino, etc. They have a β-3 adrenaline receptor agonist and are useful as drugs for the treatment and prevention of diabetes, obesity, hyperlipemia, etc.

  通式(I)所代表的化合物或其盐类，以及生产该化合物或其盐类的工艺和中间体，其中R代表氢或甲基；R1代表氢、囟素、羟基、苄氧基、氨基或羟甲基；R2代表氢、羟甲基、NHR3、SO2NR4R4或硝基；R6代表氢或低级烷基；X代表氮、氧、硫或亚甲基，但当X代表氮、氧或硫时，R9代表氢，R7和R8中的一个代表氢，另一个代表氢、氨基、乙酰氨基或羟基；当X代表亚甲基时，R7和R8各自代表氢，R9代表氢、氨基等。它们具有β-3肾上腺素受体激动剂的作用，可作为治疗和预防糖尿病、肥胖症、高脂血症等的药物。
• The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol
  作者：Chuanjun Lu、Zonghua Luo、Ling Huang、Xingshu Li

  DOI：10.1016/j.tetasy.2011.04.017

  日期：2011.4

  The asymmetric transfer hydrogenation of a series of halo-substituted aryl methyl ketones, including those substituted in both alpha-methyl and aryl rings, was studied for the preparation of chiral halohydrins. Up to 99.7% ee was obtained with 2-chloro-1-(2-chlorophenyl)ethanone as the substrate and Ru-CsDPEN as the catalyst in an HCOONa/H2O system. (R)-Clorprenaline, a drug used in the treatment of respiratory disorders, such as bronchitis and asthma, and (S)-sotalol, a class-III antiarrhythmic compound, were prepared with these chiral halohydrins. (C) 2011 Elsevier Ltd. All rights reserved.
• Tryptamine-based human β3-adrenergic receptor agonists. Part 1: SAR studies of the 7-position of the indole ring
  作者：Kazuhiro Mizuno、Masaaki Sawa、Hiroshi Harada、Hirotaka Tateishi、Mayumi Oue、Hiroshi Tsujiuchi、Yasuji Furutani、Shiro Kato

  DOI：10.1016/j.bmcl.2004.10.035

  日期：2004.12

  A series of tryptamine-based 2-thiophenesulfonamide derivatives were prepared and their agonistic activity for the beta-adrenergic receptors (ARs) was evaluated. Compound 54, containing 7-methanesulfonyloxy tryptamine, was found to be a highly potent beta(3)-AR agonist (EC50 = 0.21 nM, IA = 97%) with excellent selectivity for the beta(3)-AR over the beta(1)- and beta(2)-ARs (210- and 86-fold, respectively). (C) 2004 Elsevier Ltd. All rights reserved.