1-(2-甲基苯基)-1,4-戊二酮 | 195137-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-甲基苯基)-1,4-戊二酮
• 英文名称: 1-(o-tolyl)pentane-1,4-dione
• 英文别名: 1-(2-Methylphenyl)pentane-1,4-dione
• CAS: 195137-30-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: XRDLHHMCBNGYRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  322.6±25.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-甲基苯基)-1,4-戊二酮 在 溶剂黄146 、 gadolinium(III) trifluoromethanesulfonate 作用下， 以 水 、 乙腈 为溶剂， 反应 6.5h， 生成 (5R)-5-(azidomethyl)-3-(4-(4-((1-(3,4-difluorophenyl)-2-methyl-5-o-tolyl-1H-pyrrol-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)oxazolidin-2-one
  参考文献：
  名称：

  Anti-tubercular agents. Part 7: A new class of diarylpyrrole–oxazolidinone conjugates as antimycobacterial agents

  摘要：

  In an effort to discover new anti-tubercular agents, a series of new diarylpyrrole oxazolidinone conjugates have been designed and synthesized. The anti-tubercular activity of these new conjugates (4a-n and 5a-d) against Mycobacterium tuberculosis H(37)Rv and drug resistance strains such as M. tuberculosis Rif(R) and M. tuberculosis XDR are discussed, wherein compound 4i has been found to be the most potent amongst the series. MTT assay was performed on the active conjugates of the series (4b-f, 4i and 5c) against mouse macrophage (J-774) cells to evaluate cytotoxic effects and selective index values. In addition, these conjugates (4a-n and 5a-d) are also tested against a panel of Gram-positive and Gram-negative bacterial strains. The docking studies have been carried out to provide some insight into the mechanism of action for this class of compounds. (C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.03.027
• 作为产物：
  描述：

  2-甲基苯甲醛 在 正丁基锂 、 苯甲酸 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 26.0h， 生成 1-(2-甲基苯基)-1,4-戊二酮
  参考文献：
  名称：

  2,5-Disubstituted furans from 1,4-alkynediols

  摘要：

  1-4-Alkynediols serve as readily available starting materials for isomerisation to 1,4-diketones, which can be converted in situ into the corresponding furans by acid-catalysed dehydration. A range of 2,5-disubstituted furans was prepared using the ruthenium-based catalyst Ru(PPh3)(3)(CO)H-2 with Xantphos at 1 mol % loading. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.05.069

文献信息

• THERAPEUTIC AGENT FOR DIABETES
  申请人：Japan Tobacco Inc.

  公开号：EP0885869A1

  公开（公告）日：1998-12-23

  A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4 and R5 are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6 is a hydrogen atom or an amino-protecting group; R1 is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2 is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3 is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.

  用于治疗糖尿病的疗法剂，包括公式[I]的化合物 其中 X是公式的组 其中R4和R5相同或不同，每个都是氢原子，可选地取代的具有1至5个碳原子的烷基等等，R6是氢原子或氨基保护基团；R1是具有1至5个碳原子的可选取代烷基，具有2至6个碳原子的可选取代烯基等等，R2是氢原子，具有1至5个碳原子的可选取代烷基等等，R2'是氢原子，R3是具有1至5个碳原子的可选取代烷基等等，其前药，药用可接受盐，水合物和溶剂化物。 本发明的化合物在血糖升高状态下表现出优越的降血糖作用，但在正常范围或低血糖状态下不影响血糖，这意味着它没有低血糖等严重副作用。因此，本发明的化合物作为治疗糖尿病的药物很有用，也用作预防糖尿病慢性并发症。
• Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of γ-Diketones and γ-Ketonitriles
  作者：Yi Li、Jia-Qi Shang、Xiang-Xiang Wang、Wen-Jin Xia、Tao Yang、Yangchun Xin、Ya-Min Li

  DOI：10.1021/acs.orglett.9b00520

  日期：2019.4.5

  A novel copper-catalyzed decarboxylative oxyalkylation of alkynyl carboxylic acids with ketones and alkylnitriles via direct C(sp3)–H bond functionalization to construct new C–C bonds and C–O double bonds was developed. This transformation is featured by wide functional group compatibility and the use of readily available reagents, thus affording a general approach to γ-diketones and γ-ketonitriles

  通过直接的C（sp 3）-H键官能化来构建新的C-C键和C-O双键的新型铜催化的炔基羧酸与酮和烷基腈的脱羧氧化烷基化反应得到了发展。这种转变的特征是广泛的官能团相容性和易于使用的试剂的使用，从而为γ-二酮和γ-酮腈提供了一种通用方法。提出了一种可能的机制。
• A fluorescent target-guided Paal–Knorr reaction
  作者：Sachin B. Wagh、Vladimir Maslivetc、James J. La Clair、Alexander Kornienko

  DOI：10.1039/d0ra06962k

  日期：——

  It has become increasingly apparent that high-diversity chemical reactions play a significant role in the discovery of bioactive small molecules. Here, we describe an expanse of this paradigm, combining a ‘target-guided synthesis’ concept with Paal–Knorr chemistry applied to the preparation of fluorescent ligands for human prostaglandin-endoperoxide synthase (COX-2).

  越来越明显的是，高度多样性的化学反应在发现生物活性小分子方面发挥着重要作用。在这里，我们描述了这种范式的扩展，将“目标引导合成”概念与用于制备人前列腺素内过氧化物合酶 (COX-2) 的荧光配体的 Paal-Knorr 化学相结合。
• Catalysts for the polymerization of unsaturated compounds
  申请人：Kristen Oliver Marc

  公开号：US20050085527A1

  公开（公告）日：2005-04-21

  Bisimine compounds of the formula (I) where the symbols have the following meanings: A is a nonmetal selected from among N, S, O and P, R 1 is a radical of the formula NR 5 R 6 , R 2 is a radical of the formula NR 5 R 6 or NR 7 R 8 , alkyl, aryl or cycloalkyl, R 5 and R 6 together with the N atom form a 5-, 6- or 7-membered ring in which one or more of the —CH— or —CH 2 — groups may be replaced by suitable heteroatom groups and which may be saturated or unsaturated and unsubstituted or substituted or be fused with further carbacyclic or heterocarbacyclic 5- or 6-membered rings which may in turn be saturated or unsaturated and substituted or unsubstituted, and R 7 and R 8 are, independently of one another, alkyl, aryl or cycloalkyl radicals, and R 3 , R 4 are, independently of one another, H or alkyl, aryl or cycloalkyl radicals, and n is 1 or 2, are used to prepare bisimidinato complexes which can be used in the polymerization of unsaturated compounds.

  Bisimine化合物的化学式（I）中，符号的含义如下：A是从N、S、O和P中选取的非金属，R1是化学式NR5R6的基团，R2是化学式NR5R6或NR7R8、烷基、芳基或环烷基的基团，R5和R6与N原子一起形成一个5、6或7元环，其中一个或多个—CH—或—CH2—基团可被适当的杂原子基团取代，环可以饱和或不饱和、未取代或取代，或与进一步的碳环或杂碳环的5或6元环融合，后者可以饱和或不饱和、取代或未取代，R7和R8是彼此独立的烷基、芳基或环烷基基团，R3、R4是彼此独立的H或烷基、芳基或环烷基基团，n为1或2，用于制备可用于聚合不饱和化合物的双咪唑配合物。
• New synthesis of 1,4-diketones via rhodium-catalysed 1,4 carbonylative addition of arylboronic acids to α,β-unsaturated ketones
  作者：Mathieu Sauthier、Yves Castanet、André Mortreux

  DOI：10.1039/b403415e

  日期：——

  The reaction of various arylboronic acids with alpha,beta-unsaturated ketones under CO pressure and in the presence of rhodium catalyst yields 1,4-diketones.

  各种芳基硼酸与α，β-不饱和酮在CO压力下，在铑催化剂的存在下反应，生成1，4-二酮。