6-bromo-3-hydroxy-2-methoxybenzaldehyde | 214123-07-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-bromo-3-hydroxy-2-methoxybenzaldehyde
• CAS: 214123-07-6
• 化学式: C₈H₇BrO₃
• 分子量: 231.046
• InChiKey: ISFPJEXXAHXCAR-UHFFFAOYSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  312.6±37.0 °C(Predicted)
• 密度：
  1.653±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-3-hydroxy-2-methoxybenzaldehyde 在 dimethylamine borane 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.5h， 生成 N-<3'-(benzyloxy)-6'-bromo-2'-methoxybenzyl>-6,7-(methylenedioxy)-1-naphthylamine
  参考文献：
  名称：

  Revision of the Structure of Fagaridine Based on the Comparison of UV and NMR Data of Synthetic Compounds

  摘要：

  Fagaridine is a quaternary benzo[c]phenanthridine alkaloid, originally isolated from Fagara xanthoxyloides in 1973. The assigned structure of this alkaloid was 7-hydroxy-8-methoxy-5-methyl-2,3-(methylenedioxy)-benzo[c]phenanthridinium (1). We have synthesized this compound, coded NK109, aiming at a practical antitumor drug, and during synthetic studies we questioned the original assigned structure. Thus, we synthesized 8-hydroxy-7-methoxy-5-methyl-2,3-(methylenedioxy)benzo[c]phenanthridinium (2), isomer of the assigned structure, and compared the spectroscopic data of both 1 and 2. The NMR data of 1 and 2 were very similar, but the UV spectra were completely different. The UV data for fagaridine agreed with these for 2; consequently, the true structure of fagaridine is 2, not 1.

  DOI：

  10.1021/np980193s
• 作为产物：
  描述：

  3-羟基-2-甲氧苯甲醛 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-bromo-3-hydroxy-2-methoxybenzaldehyde
  参考文献：
  名称：

  [EN] FGFR2 INHIBITOR, PREPARATION METHOD THEREFOR, AND PHARMACEUTICAL USE THEREOF
  [FR] INHIBITEUR DU FGFR2, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION PHARMACEUTIQUE
  [ZH] FGFR2抑制剂、及其制备方法和医药用途

  摘要：

  一种通式(1)所示的化合物或其药学上可接受的盐，以及含有如通式(1)所示化合物的组合物，制备方法和其作为成纤维细胞生长因子受体2(FGFR2)抑制剂在抗肿瘤药物制备中的用途。

  公开号：

  WO2023078413A1

文献信息

• Coordination Chemistry of Cyclopropenylidene-Stabilized Phosphenium Cations: Synthesis and Reactivity of Pd and Pt Complexes
  作者：Ágnes Kozma、Tobias Deden、Javier Carreras、Christian Wille、Jekaterina Petuškova、Jörg Rust、Manuel Alcarazo

  DOI：10.1002/chem.201303686

  日期：2014.2.17

  substituents attached to the phosphorus atom. Despite of the positive charge that they bear, phosphenium cations 1 a–g still act as two‐electron donor ligands, forming adducts with PdII and PtII precursors. Conversely, in the presence of Pd0 species, an oxidative insertion of the Pd atom into the Ccarbene–phosphorus bond takes place, providing dimeric structures in which each Pd atom is bonded to a cyclopropenyl

  描述了一种通过[（i Pr 2 N）2 C 3 + Cl] BF 4与仲膦的反应直接合成环丙烯烯稳定的阳离子1 a – g的方法。通过分析Rh配合物[RhCl（CO）L 2 ]（BF 4）2中的CO拉伸频率和电化学方法评估了其供体能力。环丙烯环引起亚磷酸酯型行为，该行为可通过与磷原子相连的其他两个取代基来调节。尽管它们带有正电荷，但阳离子1 a – g仍然充当两电子给体的配体，与Pd II和Pt II前体形成加合物。相反，在存在Pd 0物种的情况下，Pd原子发生氧化插入C卡宾-磷键，从而提供二聚体结构，其中每个Pd原子均键合至环丙烯基卡宾，而两个二烷基/二芳基磷化物配体用作两个钯金中心之间的桥梁。测试了所得Pt II配合物文库的催化性能；所有的阳离子膦的加速原型6-内切2-乙炔基-1,1'-联苯的环化-Dig得到pentahelicene。最好的配体1克 被用于合成两种天然产物，金氧宾和表艾克麦芽糖苷A。
• Enantioselective total syntheses of cedrelin A and methylated paralycolin B using Pd-catalyzed asymmetric intramolecular Friedel–Crafts allylic alkylation of phenols
  作者：Yuta Suzuki、Nobuaki Matsuo、Tetsuhiro Nemoto、Yasumasa Hamada

  DOI：10.1016/j.tet.2013.05.007

  日期：2013.7

  We report the first enantioselective total syntheses of cedrelin A and methylated paralycolin B, wherein Pd-catalyzed asymmetric intramolecular Friedel–Crafts allylic alkylation of phenols was the key step.

  我们报道了雪松林A和甲基化的伞菌B的第一个对映选择性总合成物，其中Pd催化酚的不对称分子内Friedel-Crafts烯丙基烷基化是关键步骤。
• Novel Synthesis of a New Skeletal Compound Benzonaphthazepine by Regioselective C-H Activation Utilizing the Intramolecular Coordination of an Amine to Pd
  作者：Takashi Harayama、Tomonori Sato、Akihiro Hori、Hitoshi Abe、Yasuo Takeuchi

  DOI：10.1055/s-2004-822371

  日期：——

  The novel synthesis of a new skeletal compound, benzonaphthazepine, from N-bromobenzylnaphthylamine using a Pd reagent is described. In the biaryl coupling reaction of N-bromobenzylnaphthylamine using a Pd reagent, the intramolecular coordination of the benzylamino group to Pd causes regioselective C-H activation at the peri position relative to the amine group on the naphthalene ring, producing benzonaphthazepine in good to excellent yield. The bulkiness of the substituent at C7 on the naphthalene ring affects the regioselectivity of the biaryl coupling reaction.

  本研究描述了利用钯试剂从 N-溴苄基萘胺合成新骨架化合物苯并萘氮杂卓的新方法。在使用钯试剂对 N-溴苄基萘胺进行双芳基偶联反应时，苄基氨基与钯的分子内配位会导致相对于萘环上胺基的周位上的 C-H 发生区域选择性活化，从而以良好甚至极佳的收率生成苯并萘氮杂卓。萘环 C7 处取代基的体积会影响双芳基偶联反应的区域选择性。
• Novel Synthesis of Naphthobenzazepinesfrom<i>N</i>-Bromobenzylnaphthyl­aminesby Regioselective C-H Activation Utilizing the Intramolecular Coordinationof an Amine to Pd
  作者：Takashi Harayama、Tomonori Sato、Akihiro Hori、Hitoshi Abe、Yasuo Takeuchi

  DOI：10.1055/s-2003-39911

  日期：——

  In a biaryl coupling reaction of N-bromobenzylnaphthyl­amine using Pd reagent, the intramolecular coordination of the benzylamino group to Pd causes the regioselective C-H activation at the peri-position to the amine group on the naphthalene ring to produce a new skeletal compound, naphthobenzazepine, in good to excellent yield.

  在使用钯试剂对 N-溴苄基萘胺进行的双芳基偶联反应中，苄基氨基与钯的分子内配位使萘环上的胺基在近位发生区域选择性 C-H 活化，生成了一种新的骨架化合物--萘并氮杂卓，收率良好甚至极佳。
• [EN] INDAZOLE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR INHIBITING PROTEIN KINASES, AND METHODS FOR THEIR USE<br/>[FR] COMPOSES D'INDAZOLE ET COMPOSITIONS PHARMACEUTIQUES INHIBANT LES PROTEINES KINASES, ET PROCEDES D'UTILISATION DE CEUX-CI
  申请人：AGOURON PHARMA

  公开号：WO2001002369A2

  公开（公告）日：2001-01-11

  Indazole compounds that modulate and/or inhibit the activity of certain protein kinases are described. These compounds and pharmaceutical compositions containing them are capable of mediating tyrosine kinase signal transduction and thereby modulate and/or inhibit unwanted cell proliferation. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing such compounds, and to methods of treating cancer and other disease states associated with unwanted angiogenesis and/or cellular proliferation, such as diabetic retinopathy, neovascular glaucoma, rheumatoid arthritis, and psoriasis, by administering effective amounts of such compounds.

  本文描述了调节和/或抑制某些蛋白激酶活性的吲唑化合物。这些化合物和含有它们的药物组合物能够介导酪氨酸激酶信号转导，从而调节和/或抑制不需要的细胞增殖。本发明还涉及含有这些化合物的药物组合物的治疗或预防用途，并通过给予有效量的这些化合物的方法治疗癌症和其他与不需要的血管生成和/或细胞增殖有关的疾病状态，例如糖尿病视网膜病变、新生血管性青光眼、类风湿性关节炎和牛皮癣。