2-(3-甲氧基苄基)苯甲醛 | 223575-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3-甲氧基苄基)苯甲醛
• 英文名称: 2-(3-methoxybenzyl)benzaldehyde
• 英文别名: 2-[(3-methoxyphenyl)methyl]benzaldehyde
• CAS: 223575-85-7
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: RMKPFESNXCOONA-UHFFFAOYSA-N

物化性质

• 沸点：
  360.6±22.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-甲氧基苄基)苯甲醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以32%的产率得到2-methoxyanthracene
  参考文献：
  名称：

  手性碘三蝶烯：合成和催化应用

  摘要：

  AbstractNew iodotriptycenes, including some chiral derivatives, have been synthesised, and their catalytic potential towards oxidative transformations has been investigated. The enantioselectivities observed in the products using chiral iodotriptycene catalysts are low, probably owing to the large distances between the coordinating groups and the iodine moieties in these compounds.

  DOI：

  10.1002/open.202200145
• 作为产物：
  描述：

  (2-(3-methoxybenzyl)phenyl)methanol 在 silica gel 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到2-(3-甲氧基苄基)苯甲醛
  参考文献：
  名称：

  Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT_2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation

  摘要：

  The effects of 3-position substitution of 9-aminomethyl-9,10-dihydroanthracene (AMDA) on 5-HT2A receptor affinity were determined and compared to a parallel series of DOB-like 1-(2,5-dimethoxyphenyl)-2-aminopropanes substituted at the 4-position. The results were interpreted within the context of 5-HT2A receptor models that suggest that members of the DOB-like series call bind to the receptor in two distinct modes that correlate with the compounds' functional activity. Automated ligand docking and molecular dynamics suggest that all of the AMDA derivatives, the parent of which is a 5-HT2A antagonist, bind in a fashion analogous to that for the sterically demanding antagonist DOB-like compounds. The failure of the F340(6.52)L mutation to adversely affect the affinity of AMDA and the 3-bromo derivative is consistent with the proposed modes of orientation. Evaluation of ligand-receptor complex models suggest that a valine/threonine exchange between the 5-HT2A and D-2 receptors may be the origin of selectivity for AMDA and two substituted derivatives.

  DOI：

  10.1021/jm800771x

文献信息

• Synthesis of Benzoazepine Derivatives via Azide Rearrangement and Evaluation of Their Antianxiety Activities
  作者：Onrapak Reamtong、Sarawut Lapmanee、Jumreang Tummatorn、Nitwaree Palavong、Charnsak Thongsornkleeb、Somsak Ruchirawat

  DOI：10.1021/acsmedchemlett.1c00275

  日期：2021.9.9

  A new synthetic method for the construction of benzoazepine analogues has been developed employing ortho-arylmethylbenzyl azide derivatives as precursors using an azide rearrangement reaction. In this work, 14 benzoazepine compounds were successfully synthesized in moderate to excellent yields. All synthetic benzoazepines were evaluated for their cytotoxicity against normal human kidney cell line (HEK

  已经开发了一种用于构建苯并氮杂类类似物的新合成方法，该方法使用邻-芳基甲基苄基叠氮化物衍生物作为前体，使用叠氮化物重排反应。在这项工作中，以中等至优异的产率成功合成了 14 种苯并氮杂化合物。评估了所有合成苯并氮杂对正常人肾细胞系（HEK 细胞）的细胞毒性。结果表明，化合物18c在受试化合物中具有最低的细胞毒性（IC 50 = 65.68 μM），与抗焦虑药物地西泮（IC 50 = 87.90 μM）相当。根据细胞毒性结果，五种苯并氮杂类类似物（化合物18c、18h、选择 18j、18n和18p ) 来确定使用高架十字迷宫 (EPM) 和旷场测试 (OFT) 方法对应激大鼠的抗焦虑作用。有趣的是，化合物18c表现出比没有镇静作用的地西泮更好的抗焦虑活性，因为它表现出优越的超运动活性。因此，这一发现可能为开发治疗焦虑症患者的药物铺平道路。
• Therapeutic compounds
  申请人：——

  公开号：US20040229910A1

  公开（公告）日：2004-11-18

  The present invention relates to certain novel benzylamine derivatives, to processes for their preparation, to pharmaceutical formulations containing them and to their use in medical therapy, particularly in the treatment of depression.

  本发明涉及某些新型苄基胺衍生物，其制备过程，含有它们的制药配方以及它们在医学治疗中的应用，特别是在抑郁症治疗中的应用。
• Pd-Catalyzed Homologation of Arylboronic Acids as a Platform for the Diversity-Oriented Synthesis of Benzylic C–X Bonds
  作者：Allan J. B. Watson、Kane A. C. Bastick

  DOI：10.1055/a-2117-9878

  日期：2023.11

  platform for the formation of benzylic C–X bonds. Benzylboronic acid pinacol (Bpin) esters are useful synthetic intermediates but are commercially uncommon, leading to preparations that typically rely upon stoichiometric metalation. Pd-catalyzed formal homologation of arylboronic acids provides access to these compounds that, in turn, allow the formation of C–C, C–O, and C–N bonds from Pd- and Cu-mediated

  我们报告了一个用于形成苄基 C-X 键的合成平台。苄基硼酸频哪醇 (Bpin) 酯是有用的合成中间体，但在商业上并不常见，导致其制备通常依赖于化学计量金属化。钯催化的芳基硼酸的形式同系化提供了获得这些化合物的途径，这些化合物反过来又允许通过钯和铜介导的交叉偶联或氧化过程形成 C-C、C-O 和 C-N 键。这提供了多种苄醇、二芳基甲烷、苄胺和苄基醚。公开了其局限性，并且通过氯苯甲嗪类似物的产生进一步证明了其实用性。
• Ih - Modulators
  申请人：N.V. Organon

  公开号：EP2159216A1

  公开（公告）日：2010-03-03

  The present invention relates to the use of an Ih chanel modular in the manufacture of a medicament for use in psychiatry. To certain novel methanamine derivatives, to processes for their preparation, to pharmaceutical formulations containing them and to their use in medical therapy, particularly for use in psychiatry.

  本发明涉及一种 Ih chanel 模块在制造精神病用药中的用途。本发明涉及某些新型甲胺衍生物、其制备工艺、含有这些衍生物的药物制剂以及它们在医疗中的用途，特别是在精神病学中的用途。
• Controllable Chemoselectivity Cascade Reactions for the Synthesis of Phenanthrenols via Palladium‐Catalyzed‐Suzuki/Heck Reaction and Michael Addition
  作者：Phornphan Yongpanich、Kamonlak Chatrangsan、Jumreang Tummatorn、Charnsak Thongsornkleeb、Somsak Ruchirawat

  DOI：10.1002/asia.202400126

  日期：——

  Palladium, a versatile catalyst, is controllable via reaction conditions tuning. This research highlights the palladium catalyst‘s application in synthesizing phenanthrenols through a sequential cascade of Suzuki/Heck reactions between chalcone and 2-bromophenyl-boronic acid, followed by Michael addition. The order of reactions can be adjusted by manipulating solvent types and reagent concentrations

  钯是一种多功能催化剂，可通过调节反应条件进行控制。这项研究强调了钯催化剂在通过查耳酮和 2-溴苯基硼酸之间的 Suzuki/Heck 反应的连续级联合成菲酚中的应用，然后进行迈克尔加成。反应顺序可以通过控制溶剂类型和试剂浓度来调整，从而影响钯催化剂的反应活性。