4-(4-bromophenyl)nicotinaldehyde | 376646-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(4-bromophenyl)nicotinaldehyde
• 英文别名: 4-(4-bromophenyl)pyridine-3-carbaldehyde
• CAS: 376646-65-0
• 化学式: C₁₂H₈BrNO
• 分子量: 262.106
• InChiKey: POFGJNGSSAQRCE-UHFFFAOYSA-N

物化性质

• 沸点：
  390.2±32.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenyl)nicotinaldehyde 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 2-(4-(4-Bromophenyl)pyridin-3-yl)-3-isobutyloxazolidin-4-one
  参考文献：
  名称：

  Synthesis and SAR of novel 2-arylthiazolidinones as selective analgesic N-type calcium channel blockers

  摘要：

  A series of new N-type (Ca(v)2.2) calcium channel blockers derived from the 'hit' structures 2-(3-bromo-4-fluorophenyl)-3(2-pyridin-2-yiethyl)thiazolidin-4-one 9 and its 2-[4-(4-bromophenyl)pyridin-3-yl]-3-isobutyI analogue 10 is described. Extensive SAR studies using a range of synthetic approaches resulted in novel, patented compounds with IC50 values of up to 0.2 mu M in an in vitro IMR32 assay, and selectivities for N/L of up to 30-fold. The new compounds described have potential in treatment of neuropathic pain. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.098
• 作为产物：
  描述：

  4-溴苯乙酮 以 乙醚 为溶剂， 生成 4-(4-bromophenyl)nicotinaldehyde
  参考文献：
  名称：

  叔醇的Vilsmeier-Haack反应：官能化吡啶和萘啶的形成

  摘要：

  2-芳基丙烷-2-醇的Vilsmeier-Haack反应通过多次亚氨基烷基化反应进行，导致形成共轭亚胺盐，该盐在乙酸铵诱导的环化反应中以良好的收率得到4-芳基烟碱醛。在N，N-二甲基甲酰胺中，通过Vilsmeier试剂的作用，由脂肪族或脂环族酮通过添加甲基格利雅（Grignard）衍生而来的叔醇转化为取代的吡啶和萘啶，然后在乙酸铵存在下进行亲核试剂辅助的环化反应。

  DOI：

  10.1039/b105634b

文献信息

• Vilsmeier–Haack reaction of tertiary alcohols: formation of functionalised pyridines and naphthyridines
  作者：Ajith Dain Thomas、Chitoorthekkathil V. Asokan

  DOI：10.1039/b105634b

  日期：2001.10.11

  which on ammonium acetate-induced cyclisation afford 4-arylnicotinaldehydes in good yields. Tertiary alcohols derived from aliphatic or alicyclic ketones by the addition of methyl Grignard are converted into substituted pyridines and naphthyridines by the action of Vilsmeier's reagent in N,N-dimethylformamide followed by nucleophile-assisted cyclisation in the presence of ammonium acetate.

  2-芳基丙烷-2-醇的Vilsmeier-Haack反应通过多次亚氨基烷基化反应进行，导致形成共轭亚胺盐，该盐在乙酸铵诱导的环化反应中以良好的收率得到4-芳基烟碱醛。在N，N-二甲基甲酰胺中，通过Vilsmeier试剂的作用，由脂肪族或脂环族酮通过添加甲基格利雅（Grignard）衍生而来的叔醇转化为取代的吡啶和萘啶，然后在乙酸铵存在下进行亲核试剂辅助的环化反应。
• Sonogashira Couplings Catalyzed by Fe Nanoparticles Containing ppm Levels of Reusable Pd, under Mild Aqueous Micellar Conditions
  作者：Sachin Handa、Bo Jin、Pranjal P. Bora、Ye Wang、Xiaohua Zhang、Fabrice Gallou、John Reilly、Bruce H. Lipshutz

  DOI：10.1021/acscatal.9b00007

  日期：2019.3.1

  Nanoparticles derived from FeCl3 containing the ligand XPhos and only 500 ppm Pd effect Sonogashira couplings in water between rt and 45 °C. The entire aqueous reaction medium can be easily recycled using an “in-flask” extraction. Several tandem processes in one pot are illustrated, including a sequence involving five steps (10 reactions) in good overall yield.

  含有配体XPhos和仅500 ppm Pd的FeCl 3衍生的纳米粒子在rt和45°C之间的水中会影响Sonogashira偶联。整个含水反应介质可以使用“烧瓶内”萃取法轻松回收。说明了一个罐中的几个串联过程，包括一个涉及五个步骤（10个反应）且总收率良好的序列。
• NANO-TO-NANO FE/PPM Pd CATALYSIS OF CROSS-COUPLING REACTIONS IN WATER
  申请人：Lipshutz Bruce H.

  公开号：US20160339418A1

  公开（公告）日：2016-11-24

  In one embodiment, the present application discloses a catalyst composition comprising: a) a reaction solvent or a reaction medium; b) organometallic nanoparticles comprising: i) a nanoparticle (NP) catalyst, prepared by a reduction of an iron salt in an organic solvent, wherein the catalyst comprises at least one other metal selected from the group consisting of Pd, Pt, Au, Ni, Co, Cu, Mn, Rh, Jr, Ru and Os or mixtures thereof; c) a ligand; and d) a surfactant; wherein the metal or mixtures thereof is present in less than or equal to 50,000 ppm relative to the iron salt.

  在一个实施例中，本申请揭示了一种催化剂组合物，包括：a) 反应溶剂或反应介质；b) 包括：i) 通过在有机溶剂中还原铁盐而制备的纳米颗粒（NP）催化剂的有机金属纳米颗粒，其中催化剂包括来自Pd、Pt、Au、Ni、Co、Cu、Mn、Rh、Jr、Ru和Os或其混合物中至少一种其他金属；c) 配体；和d) 表面活性剂；其中金属或其混合物相对于铁盐的含量小于或等于50,000 ppm。
• [EN] FIVE-MEMBERED HETEROCYCLIC COMPOUNDS IN THE TREATMENT OF CHRONIC AND ACUTE PAIN<br/>[FR] COMPOSES HETEROCYCLIQUES A CINQ CHAINONS UTILISES DANS LE TRAITEMENT DE DOULEURS CHRONIQUES ET AIGUES
  申请人：IONIX PHARMACEUTICALS LTD

  公开号：WO2004017966A1

  公开（公告）日：2004-03-04

  Compounds of formula (I) are found to antagonise N-type calcium channels F(I) wherein R1, R2 and R4 are organic residues, Y is a linker and R3 is aryl, heteroaryl, carbocyclyl a heterocyclyl are N-type calcium channel antagonists and are therefore useful in the treatment of both chronic and acute pain.
• Synthesis and SAR of novel 2-arylthiazolidinones as selective analgesic N-type calcium channel blockers
  作者：Lars J.S. Knutsen、Christopher J. Hobbs、Christopher G. Earnshaw、Andrea Fiumana、Jenny Gilbert、Sarah L. Mellor、Fleur Radford、Nichola J. Smith、Philip J. Birch、J. Russell Burley、Stuart D.C. Ward、Iain F. James

  DOI：10.1016/j.bmcl.2006.10.098

  日期：2007.2

  A series of new N-type (Ca(v)2.2) calcium channel blockers derived from the 'hit' structures 2-(3-bromo-4-fluorophenyl)-3(2-pyridin-2-yiethyl)thiazolidin-4-one 9 and its 2-[4-(4-bromophenyl)pyridin-3-yl]-3-isobutyI analogue 10 is described. Extensive SAR studies using a range of synthetic approaches resulted in novel, patented compounds with IC50 values of up to 0.2 mu M in an in vitro IMR32 assay, and selectivities for N/L of up to 30-fold. The new compounds described have potential in treatment of neuropathic pain. (c) 2006 Elsevier Ltd. All rights reserved.