1-(3-methylphenyl)pentane-1,4-dione | 195137-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-methylphenyl)pentane-1,4-dione
• 英文别名: 1-(m-tolyl)pentane-1,4-dione
• CAS: 195137-31-6
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: YZYXZQRMVXZJKY-UHFFFAOYSA-N

物化性质

• 沸点：
  328.9±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-(3-methylphenyl)pentane-1,4-dione 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 13.0h， 生成 4-[[1-(4-Fluorophenyl)-2-methyl-5-(m-tolyl)pyrrol-3-yl]methyl]thiomorpholine
  参考文献：
  名称：

  Antimycobacterial Agents. Novel Diarylpyrrole Derivatives of BM212 Endowed with High Activity toward Mycobacterium tuberculosis and Low Cytotoxicity

  摘要：

  On the basis of suggestions derived either from a pharmacophoric model for antitubercular agents or from a structure-activity relationship analysis of many pyrroles previously described by us, we report here the design and synthesis of new analogues of 1,5-(4-chlorophenyl)-2-methyl-3-(4-methylpiperazin-1-yl)methyl-1H- pyrrole (BM212). Various substituents with different substitution patterns were added to both positions 1 and 5 of the pyrrole nucleus to evaluate their influence on the activity toward Mycobacterium tuberculosis (MTB) and atypical mycobacteria. Biological data showed that, although some nontuberculosis mycobacterial strains were found to be sensitive, MIC values were higher than those found toward MTB. The best compound (1-(4-fluorophenyl)-2-methyl-3-(thiomorpholin-4-yl)methyl-5-(4-methylphenyl)-1H-pyrrole, 5) possessed a MIC of 0.4 mu g/mL (better than BM212 and streptomycin) and a very high protection index (160), better than BM212, isoniazid, and streptomycin ( 6, 128, and 128, respectively). Finally, molecular modeling studies were performed to rationalize the activity of the new compounds in terms of both superposition onto a pharmacophoric model for antitubercular compounds and their hydrophobic character.

  DOI：

  10.1021/jm0602662
• 作为产物：
  描述：

  3-甲基苯甲醛 在 正丁基锂 、 丙酸 、 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-(3-methylphenyl)pentane-1,4-dione
  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。
• Highly selective synthesis of 1-phenylpentane-1, 4-diones, and (<i>E</i>)-5-hydroxy-5-phenylpent-3-en-2-ones catalyzed by organophosphorus compounds
  作者：Qing Zhang、Yan-Fei Qiao、Min Huang、Hong-Dong Liang、Ru-Jin Zhou

  DOI：10.1002/hc.20568

  日期：——

  1-Phenylpentane-1, 4-diones, and (E)-5-hydroxy-5-phenylpent-3-en-2-ones were synthesized via organophosphine-catalyzed addition reaction of but-3-en-2-one with aldehydes. The features of the present protocols include high selectivity, operational simplicity, atom economy, and mild reaction conditions without transition metals. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 20:425–430, 2009; Published

  1-Phenylpentane-1, 4-diones 和 (E)-5-hydroxy-5-phenylpent-3-en-2-ones 是通过 but-3-en-2-one 与醛的有机膦催化加成反应合成的. 本协议的特点包括高选择性、操作简单、原子经济性和无过渡金属的温和反应条件。© 2010 Wiley Periodicals, Inc. 杂原子化学 20:425–430, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20568
• New rhodium(II) catalyzed synthesis of 1,4-dicarbonyl compounds from α-diazo ketones using vinyl ethers as two-carbon synthons
  作者：Sengodagounder Muthusamy、Pandurangan Srinivasan

  DOI：10.1016/j.tetlet.2006.06.111

  日期：2006.8

  afforded γ-ketoaldehydes or 1,4-diketones in a facile manner. In this process, oxycyclopropanes are formed as intermediates, and are subsequently ring opened in the presence of the rhodium(II) acetate catalyst to furnish the corresponding 1,4-dicarbonyl compounds. The scope of this protocol has been demonstrated with the synthesis of a serotonin antagonist.

  乙酸铑（II）催化各种α-重氮酮与乙烯基醚的反应，可以轻松地得到γ-酮醛或1,4-二酮。在该方法中，形成氧环丙烷作为中间体，然后在乙酸铑（II）催化剂存在下将其开环以提供相应的1，4-二羰基化合物。血清素拮抗剂的合成证明了该方案的范围。
• Cobalt(II)-Catalyzed Synthesis of γ-Diketones from Aryl Alkenes and Its Utilization in the Synthesis of Various Heterocyclic Compounds
  作者：Subham Sau、Krishna Mohan Das、Bijan Mondal、Arunabha Thakur

  DOI：10.1021/acs.joc.4c00487

  日期：2024.5.17

  additive or ligand template, which further needs to be synthesized. Herein, we report the synthesis of 1,4-dicarbonyl compounds using cobalt(II) acetate as a catalyst without any expensive co-catalyst or ligand templates. This methodology has a broad substrate scope with significant yields and good functional group tolerance. Generation of unsymmetrical 1,4-dicarbonyls at room temperature and its versatile

  开发了一种地球丰富的 Co(II) 盐催化温和且经济实惠的合成路线，用于通过芳基烯烃和酮（环状和无环）之间的氧化偶联合成工业相关的 1,4-二羰基化合物（或 γ-二酮） ）分别使用TBHP和DBU作为氧化剂和碱。已知1,4-二羰基化合物是使用昂贵的金属催化剂、双催化剂或低成本金属配合物与添加剂或配体模板结合来合成的，还需要进一步合成。在此，我们报道了使用乙酸钴(II)作为催化剂合成1,4-二羰基化合物，无需任何昂贵的助催化剂或配体模板。该方法具有广泛的底物范围、显着的产量和良好的官能团耐受性。在室温下生成不对称 1,4-二羰基及其多功能合成扩展以产生具有合成和生物学价值的杂环化合物是这种新颖方法的显着特征。此外，各种受控实验，如初级动力学同位素效应研究、苯乙烯环上取代基性质变化的哈米特分析以及理论计算（密度泛函理论）揭示了这种新的、简单的原子所涉及的复杂机制。 -经济方法论。