(2-hydroxynaphthalen-1-yl)-(3,4,5-trimethoxyphenyl)methanone | 848851-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-hydroxynaphthalen-1-yl)-(3,4,5-trimethoxyphenyl)methanone
• 英文别名: 1-(3,4,5-trimethoxybenzoyl)naphthalene-2-ol；(3',4',5'-trimethoxyphenyl)-(1-naphthyl-2-ol)methanone
• CAS: 848851-59-2
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: FCUXKZCKOKLWFE-UHFFFAOYSA-N

物化性质

• 沸点：
  516.9±50.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-hydroxynaphthalen-1-yl)-(3,4,5-trimethoxyphenyl)methanone 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以72%的产率得到(4-Hydroxy-3,5-dimethoxy-phenyl)-(2-hydroxy-naphthalen-1-yl)-methanone
  参考文献：
  名称：

  使用氯化铝-二氯甲烷系统对对芳基甲基醚进行简单的区域选择性脱甲基

  摘要：

  摘要 在室温下，通过使用氯化铝-二氯甲烷体系，酚酯和二芳基酮的几种芳基甲基醚以良好的产率（53-85%）选择性地脱甲基为相应的 4-羟基衍生物。

  DOI：

  10.1081/scc-200046477
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸萘-2-基酯 在 三氯化铝 作用下， 以31%的产率得到(2-hydroxynaphthalen-1-yl)-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis of 1-(3′,4′,5′-trimethoxy) phenyl naphtho[2,1b]furan as a novel anticancer agent

  摘要：

  3',4',5'-Trimethoxy benzoyl-naphthalene 2-O-acetic acid (5) underwent base catalysed intramolecular condensation to yield exclusively 1-(3',4',5'-trimethoxy) phenyl naphtho[2,1-b]furan 8. The cyclised product 8 has been characterised by spectroscopy. The product 8 showed significant anticancer activity against human cancer cell lines COLO320DM (colon), CaCO2 (colon) and WRL68 (liver) at 0.7, 0.65 and 0.50 mu g/ml concentrations, respectively, in the in vitro MTT assay. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.105

文献信息

• Cu/Ag mediated peroxide-free synthesis of benzoylated naphthol derivatives
  作者：Subramaniyan Prasanna Kumari、Pavithira Suresh、Vijayashree Muthukumar、Subramaniapillai Selva Ganesan

  DOI：10.1016/j.tetlet.2020.152487

  日期：2020.11

  A peroxide-free methodology was developed for the synthesis of benzoylated naphthol/phenol derivatives through oxidative deamination reaction performed under aerobic reaction conditions. A synergistic combination of Cu(OTf)2 and Ag2O was used to convert the aminonaphthols and aminophenols to the corresponding benzoylated derivatives. The definite role of atmospheric oxygen to assist the reaction was

  开发了一种无氧方法，通过需氧反应条件下的氧化脱氨反应合成苯甲酰化萘酚/苯酚衍生物。Cu（OTf）2和Ag 2 O的协同组合用于将氨基萘和氨基酚转化为相应的苯甲酰化衍生物。通过在氩气氛中进行反应，证明了大气氧对反应的确定作用。
• [EN] GALLIC ACID DERIVATIVE AND PROCESS OF PREPARING THE SAME<br/>[FR] DERIVE D'ACIDE GALLIQUE ET PROCEDE DE PREPARATION CORRESPONDANT
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2005063677A1

  公开（公告）日：2005-07-14

  This invention provides a plant growth regulatory activity of a new biologically active synthetic molecule Methanone- (3', 4', 5'-trimethoxy) phenyl, 1-naphthyl, 2-O-4"-ethyl but-2"-enoate. More particularly, the invention relates to the potent plant growth promoting activity of a gallic acid derivative having the structural formulae (1) and molecular formulae C26H26O7. This invention also provides a novel process for preparation of a said molecule from a naturally occurring compound and testing it for growth regulating activity using Bacopa test system developed at CIMAP (Khanuja et al 2001).

  本发明提供了一种新的生物活性合成分子Methanone-(3'、4'、5'-三甲氧基)苯基、1-萘基、2-O-4"乙基丙烯酸酯的植物生长调节活性。更具体地说，本发明涉及一种具有结构式（1）和分子式C26H26O7的没食子酸衍生物的强效植物生长促进活性。本发明还提供了一种从天然化合物制备所述分子的新型方法，并使用在CIMAP开发的Bacopa测试系统中测试其生长调节活性（Khanuja等人，2001）。
• Synthesis of a novel plant growth promoter from gallic acid
  作者：Arvind Singh Negi、Mahinder P. Darokar、Sunil K. Chattopadhyay、Ankur Garg、Asish K. Bhattacharya、Vandana Srivastava、Suman P.S. Khanuja

  DOI：10.1016/j.bmcl.2004.11.079

  日期：2005.2

  Gallic acid has been modified to naphthophenone derivatives with esterified fatty acid side chain. Compound 12, an ethyl crotonate ester of naphthophenone derivative has shown potent auxin like growth promoter activity. This is the first example of naphthophenone derivatives with plant growth promoting activity. (C) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of gallic acid based naphthophenone fatty acid amides as cathepsin D inhibitors
  作者：Vandana Srivastava、Hari Om Saxena、Karuna Shanker、J.K. Kumar、Suaib Luqman、M.M. Gupta、S.P.S. Khanuja、Arvind S. Negi

  DOI：10.1016/j.bmcl.2006.06.010

  日期：2006.9

  Gallic acid, one of the most abundant plant phenolic acids, has been modified to cathepsin D protease inhibitors. The strategy of modification was proposed basing on some previously reported structure and activity relationship (SAR) studies. The synthesized naphthophenone fatty acid amide derivatives have been evaluated for in vitro cathepsin D inhibition activity. Two of them have shown significant inhibition activity with IC50 values of 0.06 and 0.14 mu M, respectively, as compared against pepstatin (0.0023 mu M), the most potent inhibitor known so far. The study revealed that such attempts on gallic acid based pharmacophores might result in potent inhibitors of cathepsin D. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of 1-(3′,4′,5′-trimethoxy) phenyl naphtho[2,1b]furan as a novel anticancer agent
  作者：Vandana Srivastava、Arvind S. Negi、J.K. Kumar、Uzma Faridi、Brijesh S. Sisodia、M.P. Darokar、Suaib Luqman、S.P.S. Khanuja

  DOI：10.1016/j.bmcl.2005.10.105

  日期：2006.2

  3',4',5'-Trimethoxy benzoyl-naphthalene 2-O-acetic acid (5) underwent base catalysed intramolecular condensation to yield exclusively 1-(3',4',5'-trimethoxy) phenyl naphtho[2,1-b]furan 8. The cyclised product 8 has been characterised by spectroscopy. The product 8 showed significant anticancer activity against human cancer cell lines COLO320DM (colon), CaCO2 (colon) and WRL68 (liver) at 0.7, 0.65 and 0.50 mu g/ml concentrations, respectively, in the in vitro MTT assay. (c) 2005 Elsevier Ltd. All rights reserved.