4-溴-2-(环戊基氧基)苯甲醚 | 138509-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-溴-2-(环戊基氧基)苯甲醚
• 英文名称: 4-bromo-2-cyclopentyloxyanisole
• 英文别名: 4-bromo-2-cyclopentyloxy-1-methoxy-benzene；4-Bromo-2-(cyclopentyloxy)-1-methoxybenzene；4-bromo-2-cyclopentyloxy-1-methoxybenzene
• CAS: 138509-45-2
• 化学式: C₁₂H₁₅BrO₂
• 分子量: 271.154
• InChiKey: WRLWUCCRDCLCJK-UHFFFAOYSA-N

物化性质

• 沸点：
  317.5±22.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909309090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-溴-2-甲氧基苯酚乙酸酯	5-bromo-2-methoxyphenyl acetate	66037-04-5	C9H9BrO3	245.073
  5-溴-2-甲氧基苯酚	5-bromo-2-methoxyphenol	37942-01-1	C7H7BrO2	203.035

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  3-环戊氧基-4-甲氧基苯硼酸	3-cyclopentyloxy-4-methoxyphenylboronic acid	159613-21-5	C12H17BO4	236.076

反应信息

• 作为反应物：
  描述：

  4-溴-2-(环戊基氧基)苯甲醚 在 palladium on activated charcoal 氢气 、 叔丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 咯利普兰
  参考文献：
  名称：

  Synthesis of 4-Substituted 1,5-Dihydropyrrol-2-ones and 5,6-Dihydro-1H-pyridin-2-ones by Negishi Cross-Coupling Reactions: Short Access to the Antidepressant (±)-Rolipram

  摘要：

  通过易得的溴化物3和6与各种官能化锌试剂的钯催化的根岸偶联反应,建立了一种合成目标化合物的直接方法(产率71-97%)。

  DOI：

  10.1055/s-2007-982553
• 作为产物：
  描述：

  5-溴-2-甲氧基苯甲醛 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 82.0h， 生成 4-溴-2-(环戊基氧基)苯甲醚
  参考文献：
  名称：

  Novel Selective PDE4 Inhibitors. 2. Synthesis and Structure−Activity Relationships of 4-Aryl-Substituted cis-Tetra- and cis-Hexahydrophthalazinones

  摘要：

  A series of 4-aryl-substituted cis-4a,5,8,8a-tetra- and cis-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-ones with high inhibitory activity toward cAMP-specific phosphodiesterase (PDE4) was synthesized. To study structure-activity relationships various substituents were introduced to the 2-, 3-, and 4-positions of the 4-phenyl ring. Substitution at the 4-position of the phenyl ring was restricted to a methoxy group, probably due to unfavorable steric interactions of larger groups with the binding site. The introduction of many alkoxy substituents including distinct ring systems and functional groups was allowed to the 3-position. It was found that in general the cis-4a,5,8,8a-tetrahydro-2H-phthalazin-1-ones are more potent than their hexahydrophthalic counterparts, the best activity residing in (4-imidazol-1-yl-phenoxy)butoxy analogue 16o (pIC(50) = 9.7).

  DOI：

  10.1021/jm010838c

文献信息

• Phosphodiesterase 4 inhibitors
  申请人：Dunn F. Robert

  公开号：US20070254913A1

  公开（公告）日：2007-11-01

  Selective PDE4 inhibition is achieved by aryl and heteroaryl pyrazole compounds. The compounds exhibit improved PDE4 inhibition as compared to compounds such as rolipram and show selectivity with regard to inhibition of other classes of PDEs.

  选择性PDE4抑制是通过芳基和杂环基吡唑化合物实现的。与罗利普兰（rolipram）等化合物相比，这些化合物表现出更好的PDE4抑制作用，并且在抑制其他类PDE时表现出选择性。
• Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions
  作者：José Barluenga、María Escribano、Patricia Moriel、Fernando Aznar、Carlos Valdés

  DOI：10.1002/chem.200902718

  日期：2009.12.14

  α‐Alkoxycarbonyl and α‐aminocarbonyl compounds are good substrates for the recently developed tosylhydrazide‐promoted Pd‐catalyzed cross‐coupling of carbonyls with aryl halides. The reaction gives rise to enol ethers and enamines, respectively, which are useful synthetic intermediates in heterocyclic synthesis. Otherwise, they can be hydrolyzed to give α,α‐disubstituted aldehydes.

  α-取代很好：α-烷氧羰基和α-氨基羰基化合物是最近开发的甲苯磺酰肼促进的Pd催化的羰基与芳基卤化物交叉偶联的良好底物。该反应分别产生烯醇醚和烯胺，它们是杂环合成中有用的合成中间体。否则，可以将它们水解得到α，α-二取代醛。
• Compounds containing phenyl linked to aryl or heteroaryl by an
  申请人：Rhone-Poulenc Rorer Limited

  公开号：US05935978A1

  公开（公告）日：1999-08-10

  This invention is directed to the pharmaceutical use of phenyl compounds, which are linked to an aryl moiety by various linkages, for inhibiting tumor necrosis factor. The invention is also directed to the compounds, their preparation and pharmaceutical compositions containing these compounds. Furthermore, this invention is directed to the pharmaceutical use of the compounds for inhibiting cyclic AMP phosphodiesterase.

  这项发明涉及苯基化合物的药用，这些化合物通过各种连接与芳基团相连，用于抑制肿瘤坏死因子。该发明还涉及这些化合物、它们的制备以及含有这些化合物的药物组合物。此外，这项发明还涉及这些化合物的药用，用于抑制环磷酸腺苷磷酸二酯酶。
• Enantioselective Syntheses of (-)-(<i>R</i>)-Rolipram, (-)-(<i>R</i>)-Baclofen and Other GABA Analogues via Rhodium-Catalyzed Conjugate Addition of Arylboronic Acids
  作者：Günter Helmchen、Jean-Michel Becht、Oliver Meyer

  DOI：10.1055/s-2003-42457

  日期：——

  Highly enantioselective syntheses of two important γ-aminobutyric acid (GABA) analogues, the antispastic drug (-)-(R)-Baclofen and the antidepressant agent (-)-(R)-Rolipram, are reported. Key-steps in both syntheses are the Rh-catalyzed asymmetric 1,4-additions of arylboronic acids to 4-aminobut-2,3-enoic acid derivatives.

  报道了两种重要的 γ-氨基丁酸 (GABA) 类似物，抗痉挛药物 (-)-(R)-巴氯芬和抗抑郁剂 (-)-(R)-Rolipram 的高度对映选择性合成。两种合成的关键步骤是芳基硼酸与 4-氨基丁-2,3-烯酸衍生物的 Rh 催化不对称 1,4-加成。
• Synthesis and evaluation of analogs of the phenylpyridazinone NPD-001 as potent trypanosomal TbrPDEB1 phosphodiesterase inhibitors and in vitro trypanocidals
  作者：Johan Veerman、Toine van den Bergh、Kristina M. Orrling、Chimed Jansen、Paul Cos、Louis Maes、Eric Chatelain、Jean-Robert Ioset、Ewald E. Edink、Hermann Tenor、Thomas Seebeck、Iwan de Esch、Rob Leurs、Geert Jan Sterk

  DOI：10.1016/j.bmc.2016.02.032

  日期：2016.4

  shows large differences which shows the potential for obtaining parasite selective PDE inhibitors. The results of these studies support the pharmacological validation of the Trypanosome PDEB family as novel therapeutic approach for HAT and provide as well valuable information for the design of potent TbrPDEB1 inhibitors that could be used for the treatment of this disease.

  锥虫磷酸二酯酶B1和B2（TbrPDEB1和TbrPDEB2）在布鲁氏锥虫的生命周期中起着重要作用，布鲁氏锥虫是人类非洲锥虫病（HAT）的致病性寄生虫，也被称为非洲昏睡病。击倒这两种酶会导致细胞周期停滞，并且对寄生虫具有致命性。最近，我们报道了phenylpyridazinone，NPD-001，具有低纳摩尔IC 50个在两个TbrPDEB1值（IC 50：4 1nM）和TbrPDEB2（IC 50：3 nM）的（。传染病杂志 2012，206（229）。在这项研究中，我们现在报告一系列作为TbrPDEB1抑制剂的苯基哒嗪酮类似物的第一个结构活性关系。还显示了选择的化合物是抗寄生虫的。重要的是，观察到TbrPDEB1 IC 50和EC 50与整个寄生虫之间具有良好的相关性。对TbrPDEB1和人PDE上所选化合物的SAR的初步分析显示出很大的差异，这显示出获得寄生虫选择性PDE抑制剂的潜力