1-(3-methoxyphenyl)pentane-1,4-dione | 123183-97-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-methoxyphenyl)pentane-1,4-dione
• CAS: 123183-97-1
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: WYJODSLLDYZHPN-UHFFFAOYSA-N

物化性质

• 沸点：
  341.6±22.0 °C(predicted)
• 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-(3-methoxyphenyl)pentane-1,4-dione 在 盐酸 、 三溴化硼 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 (4R,6R)-4-hydroxy-6-[2-[2-(3-hydroxyphenyl)-5-methylpyrrol-1-yl]ethyl]oxan-2-one
  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-甲氧基苯乙酮 在 溴苯 、 silver fluoride 、 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 36.17h， 生成 1-(3-methoxyphenyl)pentane-1,4-dione
  参考文献：
  名称：

  硅基烯醇醚的银催化控制分子间交叉偶联：可扩展地获得 1,4-二酮

  摘要：

  公开了一种用于甲硅烷基烯醇化物的银催化受控分子间交叉偶联的方案。该协议显示出良好的官能团耐受性，并允许有效制备一系列合成有用的 1,4-二酮。初步的机理研究表明，该反应通过一个单电子过程进行，其中涉及自由基物质，其中 PhBr 充当氧化剂。

  DOI：

  10.1021/acs.orglett.2c01477

文献信息

• Development of a Palladium-Catalyzed Carbonylative Coupling Strategy to 1,4-Diketones
  作者：Hongfei Yin、Dennis U. Nielsen、Mette K. Johansen、Anders T. Lindhardt、Troels Skrydstrup

  DOI：10.1021/acscatal.6b00733

  日期：2016.5.6

  We report on a three-component palladium-catalyzed coupling strategy for accessing a wide range of 1,4-diketones, which represent important precursors to heterocycles. Our method relies on a carbonylative Heck reaction employing substituted allylic alcohols, aryl iodides, and carbon monoxide. The reaction conditions are mild and do not require high CO pressure, and a wide functional group tolerance

  我们报告了一种三组分钯催化的偶联策略，可用于广泛的1,4-二酮，这些化合物代表杂环的重要前体。我们的方法依赖于采用取代的烯丙醇，芳基碘化物和一氧化碳的羰基Heck反应。反应条件温和并且不需要高的CO压力，并且揭示了宽的官能团耐受性，以中等至良好的产率提供了所需的1，4-二酮。此外，该方法适用于在羰基位置之一或两个位置选择性地安装13 C-碳同位素。
• 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。
• 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
  作者：Bruce D. Roth、D. F. Ortwine、M. L. Hoefle、C. D. Stratton、D. R. Sliskovic、M. W. Wilson、R. S. Newton

  DOI：10.1021/jm00163a005

  日期：1990.1

  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.
• Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones
  作者：Li Xu、Xiaoyi Liu、Gregory R. Alvey、Andrey Shatskiy、Jian-Quan Liu、Markus D. Kärkäs、Xiang-Shan Wang

  DOI：10.1021/acs.orglett.2c01477

  日期：2022.7.1

  A protocol for silver-catalyzed controlled intermolecular cross-coupling of silyl enolates is disclosed. The protocol displays good functional group tolerance and allows efficient preparation of a series of synthetically useful 1,4-diketones. Preliminary mechanistic investigations suggest that the reaction proceeds through a one-electron process involving free radical species in which PhBr acts as

  公开了一种用于甲硅烷基烯醇化物的银催化受控分子间交叉偶联的方案。该协议显示出良好的官能团耐受性，并允许有效制备一系列合成有用的 1,4-二酮。初步的机理研究表明，该反应通过一个单电子过程进行，其中涉及自由基物质，其中 PhBr 充当氧化剂。