1-hydroxy-4-methyl-2-formylnaphthalene | 59292-75-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-hydroxy-4-methyl-2-formylnaphthalene
• 英文别名: 2-formyl-4-methyl-1-naphthol；1-Hydroxy-2-formyl-4-methyl-naphthalin；1-hydroxy-4-methyl-naphthalene-2-carbaldehyde；1-Hydroxy-4-methylnaphthalene-2-carbaldehyde
• CAS: 59292-75-0
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: ITJHFZNWWSMVLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-hydroxy-4-methyl-2-formylnaphthalene 在 哌啶 、 氯化亚砜 、 水 、 potassium hydroxide 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.5h， 生成 6-methyl-N-(3-morpholinopropyl)-2-oxo-2H-benzo[h]chromene-3-carboxamide
  参考文献：
  名称：

  Synthesis of novel 3-carboxamide-benzocoumarin derivatives as orally active antithrombotic agents

  摘要：

  In an effort to develop potent antithrombotic agents, a series of novel 3-carboxamide-benzocoumarin derivatives were synthesized and screened for their in vivo antithrombotic activity. Among 20 compounds tested, the compound 12b showed the most promising antithrombotic activity which was comparable with clinically used aspirin or warfarin, but, at variance with these standard drugs, 12b did not exhibit the increased bleeding time, suggesting its potential as a novel antithrombotic agent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.100
• 作为产物：
  描述：

  1-(2-(prop-1-en-2-yl)phenyl)prop-2-yn-1-one 在 二苯基亚砜 、 (^tBuXPhos)AuNTf₂ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 25.5h， 以72%的产率得到1-hydroxy-4-methyl-2-formylnaphthalene
  参考文献：
  名称：

  Synthesis of 2-acyl-1-naphthols by gold-catalyzed oxidative cyclization of 2-alkenylphenyl alkynyl ketones

  摘要：

  The gold(I)-catalyzed oxidative cyclization of 2-alkenylphenyl alkynyl ketones employing organic oxides as oxidants has been developed. This reaction involves aromatization to furnish 2-acyl-1-naphthols. Also, 10-acyl-9-phenanthrenols are analogously produced from the reaction of allcynyl 2-biphenyl ketones. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.041

文献信息

• Efficient and General Synthesis of 3-Aryl Coumarins Using Cyanuric Chloride¹
  作者：Koneni Sashidhara、Gopala Palnati、Srinivasa Avula、Abdhesh Kumar

  DOI：10.1055/s-0031-1290344

  日期：2012.3

  protocol for a rapid synthesis of different substituted 3-aryl coumarins is reported. A series of different substituted phenyl acetic acids have been successfully reacted with different substituted 2-hydroxy benzaldehydes in the presence of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) and N-methyl morpholine to afford 3-aryl coumarins in good to excellent yields. synthesis - 3-aryl coumarins -

  报道了快速合成不同取代的3-芳基香豆素的有效且通用的方案。在氰尿酰氯（2,4,6-三氯-1,3,5-三嗪）和N-甲基吗啉的存在下，一系列不同的取代苯基乙酸已成功与不同的取代的2-羟基苯甲醛反应，得到3芳基香豆素的收率高至优异。 合成-3-芳基香豆素-氰尿酰氯-2-羟基苯甲醛 系列“新型合成方法论研究”的第八部分。
• Unusual Reaction of 6-Formyl-2-oxo-2H-benzo[h]chromene-3-carboxylic Acid Ethyl Ester with Aliphatic Amines
  作者：Koneni V. Sashidhara、Jammikuntla N. Rosaiah、Abdhesh Kumar

  DOI：10.1080/00397910902916056

  日期：2009.12.15

  The unusual reaction of coumarone systems when exposed to aliphatic amines is described. The stability and formation of these compounds is discussed with respect to its substituents at para position, and it was found that the para substituents have no role to play.

  描述了当暴露于脂肪胺时香豆酮系统的不寻常反应。这些化合物的稳定性和形成就其对位取代基进行了讨论，发现对位取代基没有任何作用。
• Discovery and synthesis of novel 3-phenylcoumarin derivatives as antidepressant agents
  作者：Koneni V. Sashidhara、Abdhesh Kumar、Manavi Chatterjee、K. Bhaskara Rao、Seema Singh、Anil Kumar Verma、Gautam Palit

  DOI：10.1016/j.bmcl.2011.02.040

  日期：2011.4

  A series of 3-phenylcoumarins were synthesized and screened for potential antidepressant activity by tail suspension test (TST) in mice. Three compounds (6, 7 and 13) exhibited impressive antidepressant activity, measured in terms of percentage decrease in immobility duration (% DID). In addition, the active antidepressant compounds were subsequently studied at their most effective dose and activity of these compounds were confirmed in forced swimming test (FST) animal model, in which the compounds at a low dose of 0.5 mg/kg significantly decreased the immobility time and exhibited greater efficacy than the reference standards fluoxetine and imipramine. The potent compounds did not show any neurotoxicity in the rotarod test and the preliminary results are promising enough to warrant further studies around this scaffold. (C) 2011 Elsevier Ltd. All rights reserved.
• Novel coumarin derivatives as potential antidyslipidemic agents
  作者：Koneni V. Sashidhara、Abdhesh Kumar、Manoj Kumar、Ravi Sonkar、Gitika Bhatia、A.K. Khanna

  DOI：10.1016/j.bmcl.2010.05.023

  日期：2010.7

  A series of novel benzocoumarin derivatives were synthesized and evaluated for their in vivo antidyslipidemic and in vitro antioxidant activities. Among 11 compounds tested, 2 compounds showed potent antidyslipidemic activity and 3 compounds showed potent antioxidant activity. (C) 2010 Elsevier Ltd. All rights reserved.
• Structure and ring-chain tautomerism of 2-hydroxy-5-methyl-3,4-benzocinnamaldehyde
  作者：I. M. Andreeva、E. M. Bondarenko、E. A. Medyantseva、R. G. Pudeyan、V. I. Minkin

  DOI：10.1007/bf00526075

  日期：1982.5