(R)-3’,5’-dibenzyloxyphenylbromohydrin | 103145-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-3’,5’-dibenzyloxyphenylbromohydrin
• 英文别名: (R)-1-(3,5-bis-benzyloxy-phenyl)-2-bromo-ethanol；(R)-3,5-dibenzyloxy-alpha-bromophenethyl alcohol；(R)-(-)-3',5'-dibenzyloxyphenylbromohydrin；(R)-(-)-3,5-dibenzyloxyphenylbromohydrin；(1R)-1-[3,5-bis(phenylmethoxy)phenyl]-2-bromoethanol
• CAS: 103145-34-2
• 化学式: C₂₂H₂₁BrO₃
• 分子量: 413.311
• InChiKey: KNEIXCFXUQTJQL-QFIPXVFZSA-N

物化性质

• 沸点：
  549.7±50.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3’,5’-dibenzyloxyphenylbromohydrin 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 20.0~120.0 ℃ 、344.75 kPa 条件下， 反应 46.0h， 生成 [3H]-(R,R)-Methoxyfenoterol
  参考文献：
  名称：

  Comparative Molecular Field Analysis of the Binding of the Stereoisomers of Fenoterol and Fenoterol Derivatives to the β₂ Adrenergic Receptor

  摘要：

  Stereoisomers of fenoterol and six fenoterol derivatives have been synthesized and their binding affinities for the beta(2) adrenergic receptor (K-i beta(2)-AR), the subtype selectivity relative to the beta(1)-AR (K-i beta(1)-AR/K-i beta(2)-AR) and their functional activities were determined. Of the 26 compounds synthesized in the study, submicromolar binding affinities were observed for (R,R)-fenoterol, the (R,R)-isomer of the p-methoxy, and (R,R)- and (R,S)-isomers of 1-naphthyl derivatives and all of these compounds were active at submicromolar concentrations in cardiomyocyte contractility tests. The K-i beta(1)-AR/K-i beta(2)-AR ratios were > 40 for (R,R)-fenoterol and the (R,R)-p-methoxy and (R,S)-1-naphthyl derivatives and 14 for the (R,R)-1-napthyl derivative. The binding data was analyzed using comparative molecular field analysis (CoMFA), and the resulting model indicated that the fenoterol derivatives interacted with two separate binding sites and one steric restricted site on the pseudo-receptor and that the chirality of the second stereogenic center affected K-i beta(2) and subtype selectivity.

  DOI：

  10.1021/jm070030d
• 作为产物：
  描述：

  3,5-二苄氧基苯乙酮 在 dimethyl sulfide borane 、 (3aS)-1-methyl-3,3-diphenyl-3a,4,5,6-tetrahydro-2H-pyrrolo[2,1-e]azaborole 、 copper(I) bromide 作用下， 以 四氢呋喃 、 氯仿 、 乙酸乙酯 为溶剂， 反应 2.5h， 生成 (R)-3’,5’-dibenzyloxyphenylbromohydrin
  参考文献：
  名称：

  一种左旋特布他林的制备方法

  摘要：

  本发明首次公开了一种左旋特布他林的制备方法，即以3，5‑二苄氧基苯乙酮为起始物料，经溴代反应后用S‑甲基CBS催化，硼烷二甲硫醚还原，与N‑苄基叔丁胺偶联后氢化脱苄基，制备光学纯的R‑特布他林，用相应的酸成盐后制备R‑特布他林的药用盐。

  公开号：

  CN106631831B

文献信息

• Surfactant-accelerated asymmetric transfer hydrogenation with recyclable water-soluble catalyst in aqueous media
  作者：Jiahong Li、Xuefeng Li、Yaping Ma、Jiashou Wu、Fei Wang、Jing Xiang、Jin Zhu、Qiwei Wang、Jingen Deng

  DOI：10.1039/c2ra22432a

  日期：——

  Water-soluble ligands (R,R)-2 were successfully prepared, in which the bis-meta-sulphonated ligand was definitely detected as the major product. The corresponding transition-metal complexes containing the ligands displayed excellent catalytic performance in asymmetric transfer hydrogenation (ATH) of aromatic ketones. Especially, the aromatic ketones with a bromine group in the α position could be smoothly

  水溶性配体（[R ，- [R ）- 2成功制备，其中，所述双元-磺化的配体肯定被检测为主要产物。含有配体的相应过渡金属络合物在芳族酮的不对称转移氢化（ATH）中表现出出色的催化性能。尤其是，在α位上具有溴基的芳族酮可以平稳地还原为预期的醇，同时保持溴基完整并具有出色的对映选择性（至多96％ee）。催化剂可以重复使用至少21次，而不会损害高转化率的对映选择性。此外，发现阳离子表面活性剂和适当的pH值对于维持高反应性是必要的。
• Compounds for the treatment of diseases
  申请人：Brown Daniel Alan

  公开号：US20050222128A1

  公开（公告）日：2005-10-06

  The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.

  本发明涉及公式（1）的化合物，以及用于制备、用于制备的中间体、含有和使用这些衍生物的组合物的过程。根据本发明的化合物在许多疾病、紊乱和状况中具有用途，特别是在炎症性、过敏性和呼吸道疾病、紊乱和状况中。
• Use of fenoterol and fenoterol analogues in the treatment of glioblastomas and astrocytomas
  申请人：Wainer Irving W.

  公开号：US09492405B2

  公开（公告）日：2016-11-15

  This disclosure concerns the discovery of the use of fenoterol and (R,R)- and (R,S)-fenoterol analogs for the treatment of a tumor expressing a β2-adrenergic receptor, such as a primary brain tumor, including a glioblastoma or astrocytoma expressing a β2-adrenergic receptor. In one example, the method includes administering to a subject a therapeutically effective amount of fenoterol, a specific fenoterol analog or a combination thereof to reduce one or more symptoms associated with the tumor, thereby treating the tumor in the subject.

  这项披露涉及发现使用非托罗尔和(R,R)-和(R,S)-非托罗尔类似物治疗表达β2肾上腺素受体的肿瘤，例如表达β2肾上腺素受体的原发性脑肿瘤，包括表达β2肾上腺素受体的胶质母细胞瘤或星形细胞瘤。在一个示例中，该方法包括向受试者施用治疗有效量的非托罗尔、特定的非托罗尔类似物或其组合，以减少与肿瘤相关的一个或多个症状，从而治疗受试者的肿瘤。
• [EN] METHODS OF REGULATING CANNABINOID RECEPTOR ACTIVITY-RELATED DISORDERS AND DISEASES<br/>[FR] PROCÉDÉS DE RÉGULATION DE TROUBLES ET MALADIES ASSOCIÉS À UNE ACTIVITÉ DE RÉCEPTEUR CANNABINOÏDE
  申请人：US HEALTH

  公开号：WO2013177418A1

  公开（公告）日：2013-11-28

  This disclosure concerns the discovery of the use of fenoterol analogues for regulating cannabinoid (CB) receptor activity-related disorders and disease, such as dysregulated CB receptors, including treating a disorder or disease, such as a glioblastoma, hepatocellular carcinoma, liver cancer, colon cancer, and/or lung cancer, which is associated with altered cannabinoid receptor activity. In one example, the method includes administering to a subject having or at risk of developing a disorder or disease regulated by CB receptor activity an effective amount of a fenoterol analogue to reduce one or more symptoms associated with the disorder or disease regulated by CB receptor activity.

  本披露涉及发现使用芬特罗类似物来调节与大麻素（CB）受体活性相关的疾病和疾病，如失调的CB受体，包括治疗与改变的大麻素受体活性相关的疾病或疾病，例如胶质母细胞瘤，肝细胞癌，肝癌，结肠癌和/或肺癌。在一个例子中，该方法包括向具有或有发展CB受体活性调节的疾病或疾病的主体施用有效量的芬特罗类似物，以减少与CB受体活性调节的疾病或疾病相关的一个或多个症状。
• WO2008/22038
  申请人：——

  公开号：——

  公开（公告）日：——