benzyl 4-(benzyloxy)-3-bromobenzoate | 628711-07-9

• 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: benzyl 4-(benzyloxy)-3-bromobenzoate
• 英文别名: benzyl 3-bromo-4-benzyloxybenzoate；Benzyl 4-benzyloxy-3-bromobenzoate；benzyl 3-bromo-4-phenylmethoxybenzoate
• CAS: 628711-07-9
• 化学式: C₂₁H₁₇BrO₃
• 分子量: 397.268
• InChiKey: BCQSFGOHLMCNRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  74-76 °C
• 沸点：
  511.6±40.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 4-(benzyloxy)-3-bromobenzoate 在 吡啶 、 四(三苯基膦)钯 、 氯化亚砜 、 palladium 10% on activated carbon 、 水 、 氢气 、 三乙胺 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、344.75 kPa 条件下， 反应 21.0h， 生成 ethyl 3-cyano-4-trifluoromethanesulfonyloxybenzoate
  参考文献：
  名称：

  Design and synthesis of substituted N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides as positive allosteric modulators of the metabotropic glutamate receptor subtype 5

  摘要：

  Based on SAR in the alkyne class of mGlu5 receptor negative allosteric modulators and a set of amide-based positive allosteric modulators, optimized substitution of the aryl 'b' ring was used to create substituted N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides. Results from an mGlu5 receptor functional assay, using calcium fluorescence, revealed varying efficacies and potencies that provide evidence that subtle changes in compounds within a close structural class can have marked effects on functional activity including switches in modes of efficacy (i.e., negative to positive allosteric modulation). Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.12.110
• 作为产物：
  描述：

  3-溴-4-羟基苯甲酸 、 溴甲苯 在 potassium carbonate 、 potassium iodide 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 72.0h， 生成 benzyl 4-(benzyloxy)-3-bromobenzoate
  参考文献：
  名称：

  [EN] CALCIUM RECEPTOR MODULATING ARYLALKYLAMINES
  [FR] ARYLALKYLAMINES MODULANT UN RECEPTEUR CALCIQUE

  摘要：

  该发明的化合物由以下一般结构（I）或其药用可接受盐所代表，以及含有它们的组合物，其中变量在此处定义，并且它们的用途是减少或抑制PTH分泌，包括减少或抑制PTH分泌的方法以及用于治疗或预防与骨骼疾病相关的疾病的方法，例如骨质疏松症，或与PTH过度分泌相关的疾病，例如甲状旁腺功能亢进症。该主题发明还涉及制备此类化合物的过程，以及在此类过程中有用的中间体。

  公开号：

  WO2003099776A1

文献信息

• Calcium receptor modulating agents
  申请人：——

  公开号：US20040082625A1

  公开（公告）日：2004-04-29

  The compounds of the invention are represented by the following general structure 1 or a pharmaceutically acceptable salt thereof, and compositions containing them, wherein the variables are defined herein, and their use to reduce or inhibit PTH secretion, including methods for reducing or inhibiting PTH secretion and methods for treatment or prophylaxis of diseases associated with bone disorders, such as osteoporosis, or associated with excessive secretion of PTH, such as hyperparathyroidism. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  本发明的化合物由以下一般结构1或其药学上可接受的盐所代表，并且含有这些化合物的组合物，其中变量在此定义，并且它们的用途是减少或抑制PTH分泌，包括减少或抑制PTH分泌的方法以及用于治疗或预防与骨疾病相关的疾病，如骨质疏松症，或与PTH过度分泌相关的疾病，如甲状旁腺功能亢进症。本发明还涉及制备这些化合物的过程，以及在这些过程中有用的中间体。
• WO2008/92072
  申请人：——

  公开号：——

  公开（公告）日：——
• Structure−Activity Relationships Comparing <i>N</i>-(6-Methylpyridin-yl)-Substituted Aryl Amides to 2-Methyl-6-(substituted-arylethynyl)pyridines or 2-Methyl-4-(substituted-arylethynyl)thiazoles as Novel Metabotropic Glutamate Receptor Subtype 5 Antagonists
  作者：Santosh S. Kulkarni、Mu-Fa Zou、Jianjing Cao、Jeffrey R. Deschamps、Alice L. Rodriguez、P. Jeffrey Conn、Amy Hauck Newman

  DOI：10.1021/jm900172f

  日期：2009.6.11

  The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in anxiety, depression, pain, mental retardation, and addiction. The potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl)pyridine (MPEP, 1) has been a critically important tool used to further elucidate the role of mGluR5 in these CNS disorders. In an effort to provide novel and structurally diverse selective mGluR5 antagonists, we previously described a set of analogues with moderate activity wherein the alkyne bond was replaced with an amide group. In the present report, extended series of both amide and alkyne-based ligands were synthesized. MGluR5 binding and functional data were obtained that identified (1) several novel alkynes with comparable affinities to 1 at mGluR5 (e.g., 10 and 20-23), but (2) most structural variations to the amide template were not well tolerated, although a few potent amides were discovered (e.g., 55 and 56). Several of these novel analogues show drug-like physical properties (e.g., cLogP range = 2-5) that support their use for in vivo investigation into the role of mGluR5 in CNS disorders.
• [EN] DEUTERIUM LABELLED DERIVATIVES OF 3-(2-HYDROXY-5-METHYPHENYL)-N,N-DIISOPROPYL-3-PHENYLPROPYLAMINE AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS DE 3-(2-HYDROXY-5-MÉTHYLVINYL)-N,N-DIISOPROPYL-3-PHÉNYLPROPYLAMINE, ET LEUR PROCÉDÉ D'UTILISATION
  申请人：CONCERT PHARMACEUTICALS INC

  公开号：WO2009126844A3

  公开（公告）日：2009-12-03
• Scalable, Divergent Synthesis of Meroterpenoids via “Borono-sclareolide”
  作者：Darryl D. Dixon、Jonathan W. Lockner、Qianghui Zhou、Phil S. Baran

  DOI：10.1021/ja303937y

  日期：2012.5.23

  A scalable, divergent synthesis of bioactive meroterpenoids has been developed. A key component of this work is the invention of "borono-sclareolide", a terpenyl radical precursor that enables gram-scale preparation of (+)-chromazonarol. Subsequent synthetic operations on this key intermediate permit rapid access to a variety of related meroterpenoids, many of which possess important biological activity.