3,4,5-三甲氧基苯甲酸萘-2-基酯 | 457923-26-1

• 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: 3,4,5-三甲氧基苯甲酸萘-2-基酯
• 英文名称: 3,4,5-trimethoxybenzoic acid naphthalene-2-yl ester
• 英文别名: 3,4,5-trimethoxybenzoic acid naphtalen-2-yl ester；2-naphthyl 3,4,5-trimethoxybenzoate；2-naphthyl, 3',4',5'-trimethoxy benzoate；2-naphthyl-3',4',5'-trimethoxy benzoate；Naphthalen-2-yl 3,4,5-trimethoxybenzoate
• CAS: 457923-26-1
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: HQZPVRRVWBLRJK-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C
• 沸点：
  466.4±12.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基苯甲酸萘-2-基酯 在 三氯化铝 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.67h， 生成 (3',4',5'-trimethoxyphenyl)-(1-naphthyl-2-(O-4''-ethyl-but-2''-enoate))methanone
  参考文献：
  名称：

  Synthesis of a novel plant growth promoter from gallic acid

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2004.11.079
• 作为产物：
  描述：

  苯甲酸萘酚酯 在 HEPES buffer 、 human liver microsomal carboxylesterase 1 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 3,4,5-三甲氧基苯甲酸萘-2-基酯
  参考文献：
  名称：

  Synthesis and evaluation of esters and carbamates to identify critical functional groups for esterase-specific metabolism

  摘要：

  In an effort to develop novel prodrugs for viral directed enzyme prodrug therapy (VDEPT) approaches to chemotherapy, eleven esters and carbamates of o-nitrophenol, p-nitrophenol, and beta-naphthol were synthesized and characterized as substrates for rabbit (rCE) and human liver (hCE1) carboxylesterases. All of the esters of o-, p-nitrophenols, and beta-naphthols showed moderate hydrolysis by both rCE and hCE1. Esters of beta-naphthols exhibited higher hydrolysis rates compared to esters of p-nitrophenols by rCE. Of the carbamates, 4-benzyl-piperazine-1-carboxylic acid 2-nitrophenol showed preferential hydrolysis by rCE compared to hCE1 with a V-max of 54.4 mumoles/min/mg, and a K-m value of 1071 muM. Substrate metabolism by a specific CE or inhibition of CEs by each compound depended on several factors, including the types of functional groups and linking moieties. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00302-x

文献信息

• An Efficient Conversion of Phenolic Esters to Benzothiazoles under Mild and Virtually Neutral Conditions
  作者：Asit K. Chakraborti、Santosh Rudrawar、Gurmeet Kaur、Lalima Sharma

  DOI：10.1055/s-2004-829089

  日期：——

  Phenolic esters are efficiently converted to 2-substituted benzothiazoles in a one-pot reaction by treatment with 2-aminothiophenol in the presence of a catalytic amount of K2CO3 in N-methyl-2-pyrrolidone (NMP) at 100 °C.

  在 100 °C 的 N-甲基-2-吡咯烷酮（NMP）中，在一定量的 K2CO3 催化下，通过与 2-氨基苯硫酚的一锅反应，酚酯可高效地转化为 2-取代的苯并噻唑。
• A Simple Regioselective Demethylation of <i>p</i>‐Aryl Methyl Ethers Using Aluminum Chloride‐Dichloromethane System
  作者：Arvind S. Negi、Sunil K. Chattopadhyay、Sachin Srivastava、Asish K. Bhattacharya

  DOI：10.1081/scc-200046477

  日期：2005.1.1

  Abstract Several aryl methyl ethers of phenolic esters and diaryl ketones have been selectively demethylated to their corresponding 4‐hydroxy derivatives by using aluminium chloride‐dichloromethane system at room temperature in good yields (53–85%).

  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。
• PROCESS FOR REGIOSELECTIVE DEMETHYLATION OF P-METHOXY GROUP IN PHENOLIC ESTER AND DIARYL KETONE MOIETIES
  申请人：Negi Singh Arvind

  公开号：US20060052463A1

  公开（公告）日：2006-03-09

  Demethylation of 3′,4′-dimethoxy or 3′,4′,5′-trimethoxy benzoic ester of a phenol is carried out in the presence of an excess of aluminum halide in an organic solvent to get 4′-Hydroxy, 3′-methoxy or 4′ hydroxy, 3′,5′-dimethoxy benzoic acid ester of a phenol. The reaction is also applicable to 3′,4′,5′-trimethoxy diaryl ketone and some natural products like reserpine.

  苯酚的3′,4′-二甲氧基或3′,4′,5′-三甲氧基苯甲酸酯的去甲基化是在有机溶剂中过量使用铝卤化物的情况下进行的，以得到苯酚的4′-羟基，3′-甲氧基或4′羟基，3′,5′-二甲氧基苯甲酸酯。该反应也适用于3′,4′,5′-三甲氧基二芳基酮和一些天然产物，如利血平。
• 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.