(R)-2-bromo-1-(3-nitrophenyl)ethanol | 193761-55-6

• 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-bromo-1-(3-nitrophenyl)ethanol
• 英文别名: (R)-2-bromo-1-(3-nitrophenyl)ethan-1-ol；(I+/-R)-I+/--(Bromomethyl)-3-nitrobenzenemethanol；(1R)-2-bromo-1-(3-nitrophenyl)ethanol
• CAS: 193761-55-6
• 化学式: C₈H₈BrNO₃
• 分子量: 246.06
• InChiKey: GGHMLSGJPIBJRA-QMMMGPOBSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  340.5±32.0 °C(Predicted)
• 密度：
  1.690±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (R)-2-bromo-1-(3-nitrophenyl)ethanol 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到(R)-(-)-(3-硝基苯基)环氧乙烷
  参考文献：
  名称：

  2,4-thiazolidinediones as potent and selective human β3 agonists

  摘要：

  Methylsulfonamide substituted 2,4-thiazolidinedione 22c is a potent (EC50 = 0.01 muM, IA = 1.19) and selective (more than 110-fold over beta (1) and beta (2) agonist activity) beta (3) agonist. This compound has also been proven to be active and selective in an in vivo mode. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00063-4
• 作为产物：
  描述：

  2-溴-3'-硝基苯乙酮 在 硼烷四氢呋喃络合物 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以77%的产率得到(R)-2-bromo-1-(3-nitrophenyl)ethanol
  参考文献：
  名称：

  1，7-环吲哚的发现是一类新型的高效，高选择性的人β3-肾上腺素能受体激动剂，具有高细胞通透性。

  摘要：

  合成和评估的新型系列的1,7环吲哚为基础的人肾上腺素能受体（β3-AR）激动剂。各种1,7-环化的吲哚部分的合成是通过Mitsunobu反应或闭环复分解（RCM）反应完成的。SAR研究表明，环尺寸的扩大导致对beta1-和beta2-AR的相当大的选择性。发现化合物26是八元环类似物，在其1,7-连接子部分具有双键，是一种有效的β3-AR激动剂（EC50 = 0.75 nM，IA = 90％），对β3的选择性非常高-AR超过beta1和beta2-AR。

  DOI：

  10.1016/j.bmc.2004.10.032

文献信息

• Process for the preparation of tricyclic amino alcohol derivatives
  申请人：ASAHI KASEI KABUSHIKI KAISHA

  公开号：US20030225289A1

  公开（公告）日：2003-12-04

  A process for the preparation of tricyclic amino alcohol derivatives including 2-[N-[2-(9H-carbazol-2-yloxy)ethyl]]amino-1-[(3-methylsulfonylamino)phenyl]ethanol useful in the treatment of diabetes, obesity, hyperlipidemia and so on; and intermediates as represented by formula (5) or (6) or the like useful in the preparation, wherein R11 is hydrogen or the like; and *1 represents an asymmetric carbon atom. 2-Halo-1-(3-nitrophenyl)ethanone derivatives and 1-(3-nitrophenyl)oxirane derivatives, which are intermediates for the preparation of tricyclic amino alcohol derivatives, are easy of purification, and particularly optically active 1-(3-nitrophenyl)oxirane derivatives are effective in enhancing the optical purities of the final products.

  一种用于制备包括2-[N-[2-(9H-咔唑-2-氧基)乙基]]氨基-1-[3-(甲磺酰氨基)苯基]乙醇在内的三环氨基醇衍生物的方法，该方法在治疗糖尿病、肥胖、高脂血症等方面有用；以及用公式(5)或(6)等表示的中间体，在制备中有用，其中R11是氢等；*1代表一个不对称碳原子。2-卤代-1-(3-硝基苯基)乙酮衍生物和1-(3-硝基苯基)环氧衍生物是用于制备三环氨基醇衍生物的中间体，易于纯化，特别是光学活性的1-(3-硝基苯基)环氧衍生物在提高最终产品的光学纯度方面是有效的。
• 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。
• NOVEL TRICYCLIC COMPOUNDS HAVING SATURATED RINGS AND MEDICINAL COMPOSITIONS CONTAINING THE SAME
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0997458A1

  公开（公告）日：2000-05-03

  Compounds represented by general formula (I) or their salts, having β3 -adrenoceptor agonism and being efficacious when employed in drugs for treating and preventing diabetes, obesity, hyperlipemia, etc. wherein R represents hydrogen or methyl; R1 represents hydrogen, halogeno, hydroxy, benzyloxy, amino or hydroxymethyl; R2 represents hydrogen, hydroxymethyl, NHR3, SO2NR4R4', or nitro (wherein R3 represents hydrogen, methyl, SO2R5, formyl or CONHR6'; R5 represents lower alkyl, benzyl or NR4R4'; R4 and R4' may be the same or different and each represents hydrogen, lower alkyl or benzyl; and R6' represents hydrogen or lower alkyl); R6 represents hydrogen or lower alkyl; n is 1 or 2; X represents secondary nitrogen, oxygen or sulfur; and when n is 1, then one of R7 and R8 represents hydrogen while another represents hydrogen, amino, acetylamino or hydroxy, or when n is 2, then R8 represents hydrogen while R7 represents hydrogen, amino, acetylamino or hydroxy.

  通式(I)所代表的化合物或其盐类，具有 β3-肾上腺素受体激动作用，在用于治疗和预防糖尿病、肥胖症、高血脂症等药物时具有疗效。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（其中 R3 代表氢、甲基、SO2R5、甲酰基或 CONHR6'；R5 代表低级烷基、苄基或 NR4R4'；R4 和 R4'可以相同或不同，各自代表氢、低级烷基或苄基；和 R6' 代表氢或低级烷基）；R6 代表氢或低级烷基；n 为 1 或 2；X 代表仲氮、氧或硫；当 n 为 1 时，则 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，或当 n 为 2 时，则 R8 代表氢，而 R7 代表氢、氨基、乙酰氨基或羟基。