2-­(6-­methoxynaphthalen-­2-­yl)acetaldehyde | 40150-97-8

• 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-­(6-­methoxynaphthalen-­2-­yl)acetaldehyde
• 英文别名: 2-(4-isobutylphenyl)acetaldehyde；p-isobutylphenylacetaldehyde；Benzeneacetaldehyde, 4-(2-methylpropyl)-；2-[4-(2-methylpropyl)phenyl]acetaldehyde
• CAS: 40150-97-8
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: HIHWQKNGFIXOTK-UHFFFAOYSA-N

物化性质

• 沸点：
  266.7±9.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-­(6-­methoxynaphthalen-­2-­yl)acetaldehyde 在 sodium chlorite 、 potassium dihydrogenphosphate 、 2,3-二甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.73h， 以89%的产率得到异丁芬酸
  参考文献：
  名称：

  Substrate-Selective Inhibition of Cyclooxygenase-2: Development and Evaluation of Achiral Profen Probes

  摘要：

  Cyclooxygenase-2 (COX-2) oxygenates arachidonic acid and the endocannabinoids 2-arachidonoylglycerol (2-AG) and arachidonoylethanolamide (AEA). We recently reported that (R)-profens selectively inhibit endocannabinoid oxygenation but not arachidonic acid oxygenation. In this work, we synthesized achiral derivatives of five profen scaffolds and evaluated them for substrate-selective inhibition using in vitro and cellular assays. The size of the substituents dictated the inhibitory strength of the analogs, with smaller substituents enabling greater potency but less selectivity. Inhibitors based on the flurbiprofen scaffold possessed the greatest potency and selectivity, with desmethylflurbiprofen (3a) exhibiting an IC50 of 0.11 mu M for inhibition of 2-AG oxygenation. The crystal structure of desmethylflurbiprofen complexed to mCOX-2 demonstrated a similar binding mode to other profens. Desmethylflurbiprofen exhibited a half-life in mice comparable to that of ibuprofen. The data presented suggest that achiral profens can act as lead molecules toward in vivo probes of substrate-selective COX-2 inhibition.

  DOI：

  10.1021/ml3001616
• 作为产物：
  描述：

  4-异丁基苯甲醛 、 甲氧基甲基三苯基氯化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 以77%的产率得到2-­(6-­methoxynaphthalen-­2-­yl)acetaldehyde
  参考文献：
  名称：

  Substrate-Selective Inhibition of Cyclooxygenase-2: Development and Evaluation of Achiral Profen Probes

  摘要：

  Cyclooxygenase-2 (COX-2) oxygenates arachidonic acid and the endocannabinoids 2-arachidonoylglycerol (2-AG) and arachidonoylethanolamide (AEA). We recently reported that (R)-profens selectively inhibit endocannabinoid oxygenation but not arachidonic acid oxygenation. In this work, we synthesized achiral derivatives of five profen scaffolds and evaluated them for substrate-selective inhibition using in vitro and cellular assays. The size of the substituents dictated the inhibitory strength of the analogs, with smaller substituents enabling greater potency but less selectivity. Inhibitors based on the flurbiprofen scaffold possessed the greatest potency and selectivity, with desmethylflurbiprofen (3a) exhibiting an IC50 of 0.11 mu M for inhibition of 2-AG oxygenation. The crystal structure of desmethylflurbiprofen complexed to mCOX-2 demonstrated a similar binding mode to other profens. Desmethylflurbiprofen exhibited a half-life in mice comparable to that of ibuprofen. The data presented suggest that achiral profens can act as lead molecules toward in vivo probes of substrate-selective COX-2 inhibition.

  DOI：

  10.1021/ml3001616

文献信息

• Catalyst and method for isomerization
  申请人：Sagami Chemical Research Center

  公开号：US04621150A1

  公开（公告）日：1986-11-04

  A catalyst for isomerization consisting essentially of a salt or complex salt represented by the formula: [ML.sub.m ].sup.n+ [Y].sub.n.sup.- (I) where M is a metal of Group IB, IIA, IIB or VIII of the periodic table, L is a ligand, Y is a conjugated base of a Bronsted acid, m is 0, 1, 2, 3 or 4 and n is 1, 2 or 3.

  一个异构化催化剂，其基本上由以下公式表示的盐或复盐组成：[ML.sub.m ].sup.n+ [Y].sub.n.sup.-（I），其中M是周期表中IB、IIA、IIB或VIII族的金属，L是配体，Y是布朗斯特酸的共轭碱，m为0、1、2、3或4，n为1、2或3。
• [EN] NOVEL PROTEIN TYROSINE PHOSPHATASE - IB INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE PROTÉINE TYROSINE PHOSPHATASE - IB
  申请人：LUPIN LTD

  公开号：WO2009109998A1

  公开（公告）日：2009-09-11

  The present invention relates to the novel compounds of the general formula (I), wherein the symbols are same as described in specification, their pharmaceutically acceptable salts, their tautomeric forms, their stereoisomers, pharmaceutical compositions containing them, to process and intermediates for the preparation of the above said compounds, having the utility of these compounds in medicine and to methods for their therapeutic use, and their use in the treatment of diabetes and related diseases.

  本发明涉及一般式（I）的新化合物，其中符号与说明书中描述的相同，它们的药学上可接受的盐，它们的互变异构体，它们的立体异构体，含有它们的制药组合物，制备上述化合物的过程和中间体，这些化合物在医学上的用途以及它们的治疗用途的方法，以及它们在糖尿病和相关疾病治疗中的用途。
• [EN] CONTINUOUS FLOW SYNTHESIS OF IBUPROFEN<br/>[FR] SYNTHÈSE EN CONTINU D'IBUPROFÈNE
  申请人：STANFORD RES INST INT

  公开号：WO2018187717A1

  公开（公告）日：2018-10-11

  This disclosure generally relates to methods of making ibuprofen, naproxen, and derivatives thereof. This disclosure also generally relates to compounds made by the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本公开涉及制备布洛芬、萘普生和其衍生物的方法。本公开还涉及由所披露方法制备的化合物。本摘要旨在作为特定领域搜索的扫描工具，并不意味着对本发明的限制。
• Preparation of novel acyl pyrazoles and triazoles by means of oxidative functionalization reactions
  作者：Geoffrey P. Wadey、Katrina E. Doherty、Arturo León Sandoval、Nicholas E. Leadbeater

  DOI：10.1515/hc-2022-0158

  日期：2023.2.7

  Novel acyl pyrazoles and acyl triazoles have been prepared by means of the oxidative amidation of aldehydes in the presence of the requisite azole. Yields range from modest to good in both cases, and some limitations of the substrate scope have been discovered. Acyl pyrazoles were prepared by treatment of a mixture of aldehyde and pyrazole with an oxoammonium salt bearing the nitrate anion. In the case of acyl triazoles, the oxidative functionalization was performed using sodium persulfate as a terminal oxidant in the presence of a catalytic quantity of a nitroxide.

  摘要 在必要的唑存在下，通过醛的氧化酰胺化反应制备了新型酰基吡唑和酰基三唑。在这两种情况下，产量从适中到良好不等，而且还发现了底物范围的一些限制。醛和吡唑的混合物与含硝酸阴离子的氧铵盐处理后，制备出了酰基吡唑。至于酰基三唑，则是在硝化物的催化下使用过硫酸钠作为末端氧化剂进行氧化官能化的。
• Method for isomerization a glycidate derivative
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0153692A2

  公开（公告）日：1985-09-04

  A catalyst for isomerization consisting essentially of a salt or complex salt represented by the formula: where M is a metal of Group IB, IIA, IIB or VIII of the periodic table, L is a ligand, Y is a conjugated base of a Bronsted acid, m is 0, 1, 2, 3 or 4 and n is 1, 2 or 3.

  一种异构化催化剂，主要由以下式子表示的盐或络合盐组成： 式中 M 为元素周期表 IB、IIA、IIB 或 VIII 族金属，L 为配体，Y 为勃朗斯特酸共轭碱，m 为 0、1、2、3 或 4，n 为 1、2 或 3。