6-bromochroman-4-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-bromochroman-4-ol
• 英文别名: (4S)-6-bromo-3,4-dihydro-2H-1-benzopyran-4-ol；(4S)-6-bromo-3,4-dihydro-2H-chromen-4-ol
• 化学式: C₉H₉BrO₂
• mdl: MFCD14705991
• 分子量: 229.073
• InChiKey: AUBCSGZQJXSWGV-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-溴色原酮 在 甲酸 、 C₃₁H₃₅ClN₂O₂RhS^(1-) 、 sodium formate 作用下， 以 水 为溶剂， 反应 3.0h， 以99%的产率得到6-bromochroman-4-ol
  参考文献：
  名称：

  Rh(II)-Cp∗–TsDPEN catalyzed aqueous asymmetric transfer hydrogenation of chromenones into saturated alcohol: CC and CO reduction in one step

  摘要：

  As an efficient catalyst for asymmetric transfer hydrogenation reaction (ATH reaction) of alpha,beta-unsaturated ketones, Rh-Cp*-TsDPEN (Cp* = 1,2,3,4,5-pentamethylcyclopenta-1,3-diene, TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenyl- ethylenediamine) shows high chemoselectivity on C=O and C=C reduction. In our method, both C=O and C=C bonds in a variety of chromenone derivatives were reduced efficiently in aqueous media, resulting in at least 98% ee and up to 99% yields in a convenient way without further purification. The product was a useful intermediate for deriving chiral chroman-4-amine, which was reported as an effective agent against hypotension and inflammatory pain by inhibiting human bradykinin B1 receptor. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.04.050

文献信息

• [EN] ALDOSTERONE SYNTHASE INHIBITORS<br/>[FR] INHIBITEURS DE L'ALDOSTÉRONE SYNTHASE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2016089800A1

  公开（公告）日：2016-06-09

  The present invention relates to compounds of the formulas (IA) and (IB) and pharmaceutically acceptable salts thereof, wherein A and R1 - R6, are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  本发明涉及式（IA）和（IB）的化合物及其药学上可接受的盐，其中A和R1-R6如本文所定义。该发明还涉及包含这些化合物的药物组合物，使用这些化合物治疗各种疾病和紊乱的方法，制备这些化合物的方法以及在这些过程中有用的中间体。
• Ruthenium complexes of new chiral phosphine‐amine‐ether ligands (Ru‐PNO) for asymmetric hydrogenation – the role of backbone chirality in pincer ligand design
  作者：Zsófia Császár、Zsanett E. Pőrgye、Evelin Tóth‐Farsang、Margit Kovács、Attila C. Bényei、József Bakos、Gergely Farkas

  DOI：10.1002/aoc.7379

  日期：2024.3

  essential element of stereochemical communication in outer sphere bifunctional catalysis. The new complexes were applied in the asymmetric hydrogenation of fused ring bicyclic ketones (i.e., 1-tetralone and 4-chromanone derivatives), a challenging substrate class, where enantioselectivities up to 97% could be obtained. Based on the spectroscopic and theoretical studies and catalytic experiments, structural

  通式为 Ph 2 PCH(R 1 )(CH 2 ) n CH(R 1 )N(R 2 )CH(R 3 )CH 2 OMe的新型手性膦胺醚 (PNO) 配体，其中 R 1、 R 2和R 3  = H或Me，n = 0或1，并且已经合成了它们的[RuCl 2 (PPh 3 )(PNO)] 类型的钌配合物。配位化合物通过 1D 和 2D NMR 光谱进行表征，通过 DFT 计算建模，并在一种情况下通过 X 射线晶体学进行分析。结合光谱和理论研究表明，P-N和N-O主链中立体元素的相对构型是决定钳型螯合物构象的关键因素，也可能影响协调立体氮的构型NH 亚基中的 NH 亚基，是外层双功能催化中立体化学通讯的重要元素。新配合物应用于稠环双环酮（即1-四氢萘酮和4-苯并二氢吡喃酮衍生物）的不对称氢化，这是一种具有挑战性的底物类别，可以获得高达97%的对映选择性。基于光谱和理论研究以及催化实验，可以确定影响
• Enantioselective acylation of chroman-4-ols catalysed by lipase from Pseudomonas cepecia (Amano PS)
  作者：S Ramadas、G.L David Krupadanam

  DOI：10.1016/s0957-4166(97)00366-2

  日期：1997.9

  Lipase Amano PS catalysed acylation of (+/-)-chroman-4-ols using vinyl acetate as the acyl donor in n-hexane gave (R)-(+)-chroman-4-ol acetates and (S)-(-)-chroman-4-ols in high enantiomeric excess. The relationship between the position of the substituents in the chroman-4-ol to the ee and the spatial characteristics of the enzyme active site are proposed. (C) 1997 Elsevier Science Ltd.