ethyl (1,4-dimethoxy-3-methylnaphthalen-2-yl)acetate | 482582-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl (1,4-dimethoxy-3-methylnaphthalen-2-yl)acetate
• 英文别名: ethyl 2-(3-methyl-1,4-dimethoxynaphthalen-2-yl)acetate；ethyl 2-(3-methyl-1,4-dimethoxynapthalen-2-yl)acetate；Ethyl 2-(1,4-dimethoxy-3-methylnaphthalen-2-yl)acetate
• CAS: 482582-94-5
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: LVKPTZAWGHJBHG-UHFFFAOYSA-N

物化性质

• 沸点：
  418.3±40.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1,4-dimethoxy-3-methylnaphthalen-2-yl)acetate 在 N-溴代丁二酰亚胺(NBS) 、 ammonium cerium(IV) nitrate 、 air 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 乙醇 、 水 、 乙腈 为溶剂， 反应 4.5h， 生成 2-isobutylbenzo[g]isoquinoline-3,5,10(2H)-trione
  参考文献：
  名称：

  New synthesis of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones

  摘要：

  Various N-substituted benz[g]isoquinoline-3,5,10(2H)-triones 7 were prepared starting from vitamin K-3 (menadione) 9. The key steps involve substitution of a benzylic bromide by a primary amine and intramolecular condensation across the ester moiety of a (3-bromo-methyl -naphth-2-yl) acetate 8 followed by oxidation with cerium(IV) ammonium nitrate (CAN) and spontaneous dehydrogenation, resulting in the title compounds 7. A selection of the synthesised new compounds was tested in vitro against Mycobacterium tuberculosis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.052
• 作为产物：
  描述：

  2-溴-3-甲基萘-1,4-二酮 在 氢氧化钾 、 正丁基锂 、 sodium dithionite 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 23.0h， 生成 ethyl (1,4-dimethoxy-3-methylnaphthalen-2-yl)acetate
  参考文献：
  名称：

  维生素K类似物的合成和蛋白质缀合研究。

  摘要：

  两种带有羧酸侧链的维生素K类似物（9a和其氘代类似物9b）是从市售甲萘醌中分六步合成的。使用EDCI / HOBT并事先形成其活化的琥珀酰亚胺酯11，将类似物9b与溶菌酶和牛血清白蛋白（BSA）偶联。偶联中的α-淀粉酶系统地控制与蛋白质缀合的类似物的数量。

  DOI：

  10.1016/j.bmc.2004.08.037

文献信息

• Synthesis and protein conjugation studies of vitamin K analogues
  作者：Richard J. Payne、Alison M. Daines、Bruce M. Clark、Andrew D. Abell

  DOI：10.1016/j.bmc.2004.08.037

  日期：2004.11

  Two vitamin K analogues bearing a carboxylic acid side chain (9a and its deuterated analogue 9b) were each synthesised in six steps from commercially available menadione. Analogue 9b was conjugated to lysozyme and bovine serum albumin (BSA) using EDCI/HOBT and by prior formation of its activated succinimidyl ester 11. Quantification of the thus formed conjugates by ESMS and LC-MS revealed that the

  两种带有羧酸侧链的维生素K类似物（9a和其氘代类似物9b）是从市售甲萘醌中分六步合成的。使用EDCI / HOBT并事先形成其活化的琥珀酰亚胺酯11，将类似物9b与溶菌酶和牛血清白蛋白（BSA）偶联。偶联中的α-淀粉酶系统地控制与蛋白质缀合的类似物的数量。
• Synthesis of 2-methyl-1,4-naphthoquinones with higher gamma-glutamyl carboxylase activity than MK-4 both in vitro and in vivo
  作者：Cees Vermeer、Cynthia van 't Hoofd、Marjo H.J. Knapen、Sofia Xanthoulea

  DOI：10.1016/j.bmcl.2016.11.073

  日期：2017.1

  cells than menaquinone-4 (MK-4, form of vitamin K2). Longer side chain lengths resulted in lower bioactivity. The in vivo vitamin K activity of the C-14 tail derivative was further tested in WKY rats receiving a vitamin K-deficient diet that resulted in a 40% decrease of prothrombin activity. The C-14 tail derivative was able to counteract the effects on vitamin K deficiency induced by the diet and resulted

  维生素K是共有2-甲基-1,4-萘醌环但在3位侧链不同的化合物的总称。我们合成了3-位不同侧链长度的新型2-甲基-1,4-萘醌衍生物。具有C-14和C-16尾巴的衍生物显示出最高的体外生物活性，从而导致MG63细胞中羧化骨钙素的合成比甲萘醌4（MK-4，维生素K2的形式）高2.5到2倍。较长的侧链长度导致较低的生物活性。在体内在接受维生素K缺乏饮食的WKY大鼠中进一步测试了C-14尾部衍生物的维生素K活性，从而导致凝血酶原活性降低了40％。C-14尾部衍生物能够抵消饮食对维生素K缺乏症的影响，并导致凝血酶原活性的完全恢复。与天然形式的维生素K相比，合成维生素K衍生物可能具有更高的生物活性和不同的药理特性，因此更适合用作补充剂或用于临床环境。
• [EN] NOVEL 2-METHYL-1,4-NAPHTHOQUINONE DERIVATIVES AND PRECURSORS THEREOF, HAVING VITAMIN K ACTIVITY<br/>[FR] NOUVEAUX DÉRIVÉS DE 2-MÉTHYL-1,4-NAPHTOQUINONE ET PRÉCURSEURS DE CEUX-CI, AYANT UNE ACTIVITÉ VITAMINE K
  申请人：NATTOPHARMA ASA

  公开号：WO2011098545A1

  公开（公告）日：2011-08-18

  New 2-methyl-1,4-naphthoquinone derivatives with vitamin K activity are provided having the general formula (1): wherein R is a aliphatic group with 12 to 50 carbon atoms. Preferably, R is a straight or branched C12-50 alkylgroup or a straight or branched C12-50 alkenyl group with 1 to 12 unsaturated bonds. Of these, the compound of formula (1) in which R is a straight C14 alkyl group is most preferred. Pharmaceutical and nutraceutical compositions comprising at least one compound of formula (1) or a pharmacologically active precursor there of are also provided.
• Efficacy of peptide nucleic acid and selected conjugates against specific cellular pathologies of amyotrophic lateral sclerosis
  作者：Elisse C. Browne、Sonam Parakh、Luke F. Duncan、Steven J. Langford、Julie D. Atkin、Belinda M. Abbott

  DOI：10.1016/j.bmc.2016.02.022

  日期：2016.4

  Cellular studies have been undertaken on a nonamer peptide nucleic acid (PNA) sequence, which binds to mRNA encoding superoxide dismutase 1, and a series of peptide nucleic acids conjugated to synthetic lipophilic vitamin analogs including a recently prepared menadione (vitamin K) analog. Reduction of both mutant superoxide dismutase 1 inclusion formation and endoplasmic reticulum stress, two of the

  已经对与编码超氧化物歧化酶1的mRNA结合的九聚体肽核酸（PNA）序列以及与包括最近制备的甲萘醌（维生素K）类似物的合成亲脂性维生素类似物缀合的一系列肽核酸进行了细胞研究。首次报道了通过制备的两种PNA寡聚体减少突变型超氧化物歧化酶1包涵体形成和内质网应激，这是肌萎缩性侧索硬化的两个关键细胞病理学特征。
• New synthesis of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones
  作者：Jan Jacobs、Sven Claessens、Bart Kesteleyn、Kris Huygen、Norbert De Kimpe

  DOI：10.1016/j.tet.2006.12.052

  日期：2007.3

  Various N-substituted benz[g]isoquinoline-3,5,10(2H)-triones 7 were prepared starting from vitamin K-3 (menadione) 9. The key steps involve substitution of a benzylic bromide by a primary amine and intramolecular condensation across the ester moiety of a (3-bromo-methyl -naphth-2-yl) acetate 8 followed by oxidation with cerium(IV) ammonium nitrate (CAN) and spontaneous dehydrogenation, resulting in the title compounds 7. A selection of the synthesised new compounds was tested in vitro against Mycobacterium tuberculosis. (c) 2007 Elsevier Ltd. All rights reserved.