1-[2-(甲氧基)苯基]-戊烷-1,4-二酮 | 104562-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[2-(甲氧基)苯基]-戊烷-1,4-二酮
• 英文名称: 1-[2-(methoxy)phenyl]-pentane-1,4-dione
• 英文别名: 1-(2-methoxy-phenyl)-pentane-1,4-dione；1-(2-Methoxyphenyl)pentane-1,4-dione
• CAS: 104562-48-3
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: HXGVTQMCAJDVRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  102 °C(Press: 0.80 Torr)
• 密度：
  1.076±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-[2-(甲氧基)苯基]-戊烷-1,4-二酮 在 盐酸 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 溶剂黄146 为溶剂， 反应 8.0h， 生成 3-[2-(2-Methoxy-phenyl)-5-methyl-pyrrol-1-yl]-propionaldehyde
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 1. trans-6-(2-Pyrrol-1-ylethyl)-4-hydroxypyran-2-ones, a novel series of HMG-CoA reductase inhibitors. 1. Effects of structural modifications at the 2- and 5-positions of the pyrrole nucleus

  摘要：

  A novel series of trans-6-(2-pyrrol-1-ylethyl)-4-hydroxypyran-2-ones and their dihydroxy acid derivatives were prepared and evaluated for their ability to inhibit the enzyme HMG-CoA reductase in vitro. A systematic study of substitution at the 2- and 5-positions of the pyrrole ring revealed that optimum potency was realized with the 2-(4-fluorophenyl)-5-isopropyl derivative 8x, which possessed 30% of the in vitro activity of the potent fungal metabolite compactin (I). A molecular modeling analysis led to the description of a pharmacophore model characterized by (A) length limits of 5.9 and 3.3 A for the 2- and 5-substituents, respectively, as well as an overall width limit of 10.6 A across the pyrrole ring from the 2- to the 5-substituent and (B) an orientation of the ethyl(ene) bridge to the 4-hydroxypyran-2-one ring nearly perpendicular to the planes of the parent pyrrole, hexahydronaphthalene, and phenyl rings of the structures examined (Figure 3, theta = 80-110 degrees). Attempts to more closely mimic compactin's polar isobutyric ester side chain with the synthesis of 2-phenylpyrroles containing polar phenyl substituents resulted in analogues with equal or slightly reduced potencies when compared to the 2-[(unsubstituted or 4-fluoro)phenyl]pyrroles, supporting the hypothesis that inhibitory potency is relatively insensitive to side-chain polarity or charge distribution in this area.

  DOI：

  10.1021/jm00163a005
• 作为产物：
  描述：

  3-(2-methoxyphenyl)prop-2-ynoic acid 、 丙酮 在 copper(II) perchlorate hexahydrate 、 水 、 manganese(III) triacetate dihydrate 、 碳酸氢钠 、 过氧化苯甲酰 作用下， 反应 6.0h， 以57%的产率得到1-[2-(甲氧基)苯基]-戊烷-1,4-二酮
  参考文献：
  名称：

  铜催化炔基羧酸的脱羧氧化烷基化：γ-二酮和γ-乙腈的合成

  摘要：

  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。

  DOI：

  10.1021/acs.orglett.9b00520

文献信息

• Dimethylaluminum methaneselenolate—a useful reagent for the preparation of selenoesters. A new friedel-crafts acylation procedure promoted by Cu(I)
  作者：Alan P. Kozikowski、Anthony Ames

  DOI：10.1016/s0040-4020(01)96721-3

  日期：1985.1

  The preparation of a new aluminum reagent, dmiethylaluminum methaneselenolate (Me2AlSeMe) is described. The reactivity of this aluminum reagent toward a variety of organic substrates has been studied. Me2AlSeMe will convert O-alkyl esters to selenoesters in high yield. These selenoesters function as extremely reactive acyl transfer agents and are converted to acids, esters, and amides on reaction with

  描述了一种新的铝试剂，二甲基亚乙基甲烷硒酸铝（Me 2 AlSeMe）的制备。已经研究了这种铝试剂对多种有机底物的反应性。Me 2 AlSeMe将以高收率将O-烷基酯转化为硒酸酯。这些硒酸酯起极活泼的酰基转移剂的作用，并在存在亲脂性金属阳离子的情况下与水，醇或胺反应，转化为酸，酯和酰胺。此外，当使用三氟甲磺酸亚铜作为亲油性金属阳离子时，硒酸酯将酰化反应性芳烃和杂环化合物。后者的转化构成了Friedel-Crafts酰化反应的新的过渡金属促进的变体。
• 10.1021/acs.joc.4c00487
  作者：Sau, Subham、Das, Krishna Mohan、Mondal, Bijan、Thakur, Arunabha

  DOI：10.1021/acs.joc.4c00487

  日期：——

  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。
• Identification of a novel pyrrole derivative endowed with antimycobacterial activity and protection index comparable to that of the current antitubercular drugs streptomycin and rifampin
  作者：Mariangela Biava、Giulio Cesare Porretta、Giovanna Poce、Claudio Battilocchio、Salvatore Alfonso、Alessandro De Logu、Nadia Serra、Fabrizio Manetti、Maurizio Botta

  DOI：10.1016/j.bmc.2010.09.006

  日期：2010.11.15

  A hit optimization procedure based on isosteric and bioisosteric replacement of decorating groups at both the N1 and the C5 phenyl rings of 1,5-diarylpyrroles led to identification of 4-((1-(4-fluorophenyl)-2-methyl- 5-(4-(methylthio) phenyl)-1H-pyrrol-3-yl) methyl) thiomorpholine that is characterized by a very high activity toward both Mycobacterium tuberculosis 103471 and H37Rv strains (MIC values of 0.125 mu g/mL), and a safe profile in terms of cytotoxicity (CC(50) of > 128 mu g/mL) and protection index (> 1000). Antitubercular activity and protection index of the new compound are comparable to those found for the current antitubercular drugs streptomycin and rifampin. (C) 2010 Elsevier Ltd. All rights reserved.
• KOZIKOWSKI, A. P.;AMES, A., TETRAHEDRON, 1985, 41, N 21, 4821-4834
  作者：KOZIKOWSKI, A. P.、AMES, A.

  DOI：——

  日期：——
• 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。