3,4-二羟基-5-(3-甲基-2-丁烯-1-基)苯甲醛 | 161095-35-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,4-二羟基-5-(3-甲基-2-丁烯-1-基)苯甲醛
• 英文名称: 3,4-dihydroxy-5-(3’-methyl-2’-buten-1’-yl)benzaldehyde
• 英文别名: 3,4-Dihydroxy-5-(3-methylbut-2-enyl)benzaldehyde
• CAS: 161095-35-8
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: DIYXVDVQPLASLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二羟基-5-(3-甲基-2-丁烯-1-基)苯甲醛 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 silica gel 作用下， 以19%的产率得到montadial A
  参考文献：
  名称：

  Application of benzyl protecting groups in the synthesis of prenylated aromatic compounds

  摘要：

  Benzyl ethers have proven to be useful protecting groups for synthesis of phenols bearing isoprenoid chains because the benzyl groups can tolerate the conditions of halogen-metal exchange used to introduce the side chains yet are cleaved in good yields upon treatment with sodium s-butanol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.187
• 作为产物：
  描述：

  2-[3-(3-Methylbut-2-enyl)-4,5-bis(phenylmethoxy)phenyl]-1,3-dioxolane 在 sodium 作用下， 以 仲丁醇 为溶剂， 以76%的产率得到3,4-二羟基-5-(3-甲基-2-丁烯-1-基)苯甲醛
  参考文献：
  名称：

  Application of benzyl protecting groups in the synthesis of prenylated aromatic compounds

  摘要：

  Benzyl ethers have proven to be useful protecting groups for synthesis of phenols bearing isoprenoid chains because the benzyl groups can tolerate the conditions of halogen-metal exchange used to introduce the side chains yet are cleaved in good yields upon treatment with sodium s-butanol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.187

文献信息

• Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods
  申请人：——

  公开号：US20030073712A1

  公开（公告）日：2003-04-17

  Cytoprotective compounds, many of which are phenolic derivatives characterized by a substituted phenol having certain conjugated bonds, are useful in the treatment of certain ischemic or inflammatory conditions, including but not limited to stroke, myocardial infarction, congestive heart failure, and skin disorders characterized by inflammation or oxidative damage. They are also useful in the manufacture of pharmaceutical and cosmetic formulations for the treatment of such conditions.

  细胞保护化合物，其中许多是酚类衍生物，其特点是具有特定共轭键的取代酚，对于治疗某些缺血或炎症性疾病非常有用，包括但不限于中风、心肌梗死、充血性心力衰竭以及以炎症或氧化损伤为特征的皮肤疾病。它们还可用于制造用于治疗这些疾病的药物和化妆品配方。
• SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES
  作者：MAURICIO E OSORIO、KAROL A QUIROZ、MARCELA A CARVAJAL、ALEJANDRA P VERGARA、ELIZABETH Y SÁNCHEZ、CESAR E GONZÁLEZ、KAREN S CATALÁN

  DOI：10.4067/s0717-97072016000300018

  日期：——

  The syntheses of six prenylated acetophenone and benzaldehyde derivatives and their anti-phytopathogenic and antioxidant activities are reported. These compounds were obtained by electrophilic aromatic substitution (SEAr) of the corresponding arenes and 3-methyl-2-buten-1-ol using ZnCl2 as a Lewis acid catalyst in ethyl acetate. Reasonable to good yields were obtained based on unrecovered aromatic starting material (45-73%). All the synthesized compounds were evaluated against phytopathogenic gram-negative bacteria Agrobacterium tumefaciens, Pseudomonas syringae and Erwinia carotovora and plant fungal pathogens Botrytis cinerea, Phytophthora cinnamomi and Gibberella fujikuroi. The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay and expressed as half maximal inhibitory concentration (IC50) values in mu M concentrations. The antioxidant activity went from 27.20 mu M to > 100 mu M. Compound 11 showed statistically significant inhibition of the growth of Botrytis cinerea, and compounds 13 and 15 showed statistically significant inhibition of the growth of Phytophthora cinnamomi, with respect to negative control fungal growth. All six compounds showed bacteriostatic effects against gram-negative plant pathogenic bacteria with IC50 values between 250 and <3.9 mu M.
• CYTOPROTECTIVE COMPOUNDS, PHARMACEUTICAL AND COSMETIC FORMULATIONS, AND METHODS
  申请人：Galileo Pharmaceuticals, Inc.

  公开号：EP1435894A2

  公开（公告）日：2004-07-14
• EP1435894A4
  申请人：——

  公开号：EP1435894A4

  公开（公告）日：2005-07-06
• US7629375B2
  申请人：——

  公开号：US7629375B2

  公开（公告）日：2009-12-08