methyl 4-formyl-1-naphthoate | 62855-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-formyl-1-naphthoate
• 英文别名: methyl 4-formylnaphthalene-1-carboxylate
• CAS: 62855-40-7
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: RQODTKJVTXOAHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-formyl-1-naphthoate 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-甲酰基-萘-1-羧酸二乙基酰胺
  参考文献：
  名称：

  Optimization of Alkylidene Hydrazide Based Human Glucagon Receptor Antagonists. Discovery of the Highly Potent and Orally Available 3-Cyano-4-hydroxybenzoic Acid [1-(2,3,5,6-Tetramethylbenzyl)-1H-indol-4-ylmethylene]hydrazide

  摘要：

  Highly potent human glucagon receptor (hGluR) antagonists have been prepared employing both medicinal chemistry and targeted libraries based on modification of the core (proximal) dimethoxyphenyl group, the benzyl ether linkage, as well as the (distal) benzylic aryl group of the lead 2, 3-eyano-4-hydroxybenzoic acid (3,5-dimethoxy-4-isopropylbenzyloxybenzylidene)hydrazide. Electron-rich proximal aryl moieties such as mono- and dimethoxy benzenes, naphthalenes, and indoles were found to be active. The SAR was found to be quite insensitive regarding the linkage to the distal aryl group, since long and short as well as polar and apolar linkers gave highly potent compounds. The presence of a distal aryl group was not crucial for obtaining high binding affinity to the hGluR. In many cases, however, the affinity could be further optimized with substituted distal aryl groups. Representative compounds have been tested for in vitro metabolism, and structure-metabolism relationships are described. These efforts lead to the discovery of 74, NNC 25-2504, 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6-tetramethylbenzyl)-1H-indol-4-ylmethylenelhydrazide, with low in vitro metabolic turnover. 74 was a highly potent noncompetitive antagonist of the human glucagon receptor (IC50 = 2.3 nM, K-B = 760 pM) and of the isolated rat receptor IC50 = 430 pM, K-B = 380 pM). Glucagon-stimulated glucose production from isolated primary rat hepatocytes was inhibited competitively by 74 (K-i = 14 nM). This compound was orally available in dogs (F-po = 15%) and was active in a glucagon-challenged rat model of hyperglucagonemia and hyperglycemia.

  DOI：

  10.1021/jm0208572
• 作为产物：
  描述：

  4-溴-1-萘甲酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 硫酸 、 碳酸氢钠 、 臭氧 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 21.0h， 生成 methyl 4-formyl-1-naphthoate
  参考文献：
  名称：

  ISOXAZOLINE OXIMES AS ANTIPARASITIC AGENTS

  摘要：

  这项发明涉及公式（1）的萘异噁唑啉肟衍生物的几何异构体、立体异构体、药用或兽医学上可接受的盐、组合物以及它们作为动物寄生虫药的用途。变量R1a、R1b、R1c、R2、R3如本文所述。

  公开号：

  US20120077765A1

文献信息

• Glucagon antagonists/inverse agonists
  申请人：Novo Nordisk A/S

  公开号：US06613942B1

  公开（公告）日：2003-09-02

  Non-peptide compounds comprising a central hydrazide motif and methods for the synthesis thereof are disclosed. The compounds act to antagonize the action of the glucagon peptide hormone.

  本发明公开了包含中央腙基结构的非肽化合物及其合成方法。这些化合物具有拮抗胰高血糖素肽激素作用的作用。
• Novel unsymmetrically π-elongated porphyrin for dye-sensitized TiO₂cells
  作者：Masanobu Tanaka、Shinya Hayashi、Seunghun Eu、Tomokazu Umeyama、Yoshihiro Matano、Hiroshi Imahori

  DOI：10.1039/b702501g

  日期：——

  A novel naphthyl-fused zinc porphyrin carboxylic acid has been synthesized and employed successfully in a dye-sensitized TiO2 solar cell, with a power conversion efficiency of 4.1%, which is improved by 50% relative to the unfused porphyrin reference cell.

  合成了一种新型萘融合锌卟啉羧酸，并成功应用于染料敏化的TiO2太阳能电池，功率转换效率达到4.1%，比未融合的卟啉参考电池提高了50%。
• Synthesis and Biological Activity of New 3-Hydroxy-3-methylglutaryl Coenzyme A (HMG-CoA) Synthase Inhibitors: 2-Oxetanones with a Side Chain Mimicking the Folded Structure of 1233A.
  作者：Hirokazu HASHIZUME、Hajime ITO、Kohji YAMADA、Hajime NAGASHIMA、Munefumi KANAO、Hiroshi TOMODA、Toshiaki SUNAZUKA、Hidetoshi KUMAGAI、Satoshi OMURA

  DOI：10.1248/cpb.42.512

  日期：——

  To mimic the folded side chain conformation of 1233A (1), which is a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitor, 1233A analogs with aromatic rings in the side chain were synthesized. The 2-oxetanone moiety was kept intact. Among 1233A and its synthetic analogs, trans-3-hydroxymethyl-4-[2-(7-methoxycarbonyl-1-naphthyl)ethyl]-2-oxetanone (23) showed the highest HMG-CoA synthase inhibitory activity in vitro. The structure-activity relationship at the side chain is discussed.

  为模拟1233A（1）的折叠侧链构象，该化合物是一种3-羟基-3-甲基戊二酰辅酶A（HMG-CoA）合酶抑制剂，合成了侧链含有芳环的1233A类似物。其中2-恶坦酮部分保持不变。在1233A及其合成类似物中，反式-3-羟甲基-4-[2-(7-甲氧羰基-1-萘基)乙基]-2-恶坦酮（23）显示了最高的HMG-CoA合酶体外抑制活性。讨论了侧链上的构效关系。
• TiCl4-mediated olefination of aldehydes with acetic acid and alkyl acetates: a stereoselective approach to (E)-α,β-unsaturated carboxylic acids and esters
  作者：John Kallikat Augustine、Chandrakantha Boodappa、Srinivasa Venkatachaliah、Ayyampillai Mariappan

  DOI：10.1016/j.tetlet.2014.04.098

  日期：2014.6

  the preparation of α,β-unsaturated carboxylic acids and corresponding esters with (E)-stereoselectivity via the TiCl4-mediated olefination of aldehydes. The method, which uses readily available acetic acid or its alkyl esters as active methylene partners, is more flexible and complementary to conventional routes in the preparation of (E)-cinnamic acid derivatives.

  已经开发了一种新的方法，用于通过TiCl 4介导的醛的烯化反应制备具有（E）-立体选择性的α，β-不饱和羧酸和相应的酯。该方法使用现成的乙酸或其烷基酯作为活性亚甲基伴侣，在制备（E）-肉桂酸衍生物时，它比常规方法更具灵活性和互补性。
• Overcoming <i>peri</i>- and <i>ortho</i>-selectivity in C–H methylation of 1-naphthaldehydes by a tunable transient ligand strategy
  作者：Yujian Mao、Jing Jiang、Dandan Yuan、Xiuzhen Chen、Yanan Wang、Lihong Hu、Yinan Zhang

  DOI：10.1039/d1sc05899a

  日期：——

  Aiming to introduce this smallest alkyl handle, a highly regioselective peri- and ortho-C–H methylation of 1-naphthaldehyde by using a transient ligand strategy has been developed. A series of methyl-substituted naphthalene frameworks have been prepared in moderate to excellent yields. Mechanistic studies demonstrate that peri-methylation is controlled by the higher electronic density of the peri-position

  甲基广泛存在于生物活性分子中，位点特异性甲基化已成为其结构功能化的重要策略。为了引入这种最小的烷基手柄，我们开发了一种通过使用瞬时配体策略对 1-萘醛进行高度区域选择性的邻位和邻位-C–H 甲基化的方法。一系列甲基取代的萘骨架已以中等至优异的产率制备。机理研究表明，邻甲基化是由1-萘醛邻位较高的电子密度以及中间5,6-稠合双环钯环的形成控制的，而实验研究和理论计算推断，5元环1-萘醛邻位的铱环通过周围环和邻环之间的相互转化导致能量上有利的邻甲基化。重要的是，为了证明该方法的合成效用，我们证明该策略可以作为合成多取代萘基生物活性分子和天然产物的平台。