3-(3,4-二甲基苯基)-3-氧代丙酸甲酯 | 676348-54-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(3,4-二甲基苯基)-3-氧代丙酸甲酯
• 英文名称: methyl 3-(3,4-dimethylphenyl)-3-oxopropanoate
• CAS: 676348-54-2
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: NPYPTOMABNEIIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,4-二甲基苯基)-3-氧代丙酸甲酯 在 sodium hydroxide 、 高氯酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 26.0h， 生成 <3,4-Dimethyl-phenyl>-isonitrosomethyl-keton
  参考文献：
  名称：

  One-pot synthesis of 3-amino-4-aryl- and 3-amino-4-hetarylfurazans

  摘要：

  开发了一种“一锅法”合成3-氨基-4-芳基和3-氨基-4-杂芳基呋咱的方法，该方法利用β-芳基和4-β-杂芳基-β-氧代酸酯。

  DOI：

  10.1007/s11172-005-0359-4
• 作为产物：
  描述：

  碳酸二甲酯 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 16.17h， 生成 3-(3,4-二甲基苯基)-3-氧代丙酸甲酯
  参考文献：
  名称：

  [EN] SUBSTITUTED HETEROCYCLIC COMPOUNDS AND METHODS OF USE
  [FR] COMPOSES HETEROCYCLIQUES SUBSTITUES ET LEURS METHODES D'UTILISATION

  摘要：

  公开号：

  WO2005070932A3

文献信息

• Synthesis of Functionalized Imidazolium Salts via Iodine-Mediated Annulations of Enamines
  作者：Biao Xia、Wenjun Chen、Qiongli Zhao、Wenquan Yu、Junbiao Chang

  DOI：10.1021/acs.orglett.9b00541

  日期：2019.4.19

  A novel annulation reaction of two enamine molecules with iodine under basic conditions to form 4-functionalized imidazolium salts has been established. In this reaction, iodine acts as both an iodinating reagent and a Lewis acid catalyst. Features of this synthetic method include facilitative preparation of substrates, no use of transition metals, mild reaction conditions, simplicity of operation

  建立了在碱性条件下两个烯胺分子与碘的新型环化反应，形成4-官能化的咪唑鎓盐。在该反应中，碘既充当碘化试剂又充当路易斯酸催化剂。这种合成方法的特点包括便于制备底物，不使用过渡金属，温和的反应条件，操作简便和克级合成。
• Synthesis of 1,4-Dihydropyridines and Related Heterocycles by Iodine-Mediated Annulation Reactions of <i>N</i>-Cyclopropyl Enamines
  作者：Lanlan Wei、Manman Wang、Yifei Zhao、Yingchao Fang、Zongxiang Zhao、Biao Xia、Wenquan Yu、Junbiao Chang

  DOI：10.1021/acs.orglett.1c03859

  日期：2021.12.17

  The annulation of N-cyclopropyl enamines to produce 1,4-dihydropyridine (1,4-DHP) derivatives is described. In the presence of molecular iodine (I2), an N-cyclopropyl enamine substrate undergoes iodination, opening of the cyclopropyl ring, and annulation with a second molecule of the substrate to form the 1,4-DHP product. This reaction is amenable to gram-scale operations under mild reaction conditions

  描述了N-环丙基烯胺的环化以产生 1,4-二氢吡啶 (1,4-DHP) 衍生物。在分子碘(I 2 )存在下，N-环丙基烯胺底物经历碘化、环丙基环开环和与底物的第二分子环化以形成1,4-DHP产物。该反应可在温和的反应条件下进行克级操作，无需过渡金属。1,4-DHP 的进一步转化导致相关的吡啶和双环框架。
• [EN] PHENETHYLAMIDE DERIVATIVES AND THEIR HETEROCYCLIC ANALOGUES<br/>[FR] DÉRIVÉS DE PHÉNÉTHYLAMIDE ET LEURS ANALOGUES HÉTÉROCYCLIQUES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2010044054A1

  公开（公告）日：2010-04-22

  The invention relates to novel phenethylamide derivatives and their heterocyclic analogues of formula (I), wherein A, B, R1, R2 and R3 are as described in the application, and to the use of such compounds, or of pharmaceutically acceptable salts of such compounds, as medicaments, especially as orexin receptor antagonists.

  这项发明涉及新型苯乙酰胺衍生物及其异环类似物，其化学式为(I)，其中A、B、R1、R2和R3如申请中所述，并且涉及将这种化合物或这种化合物的药用可接受盐用作药物，特别是促进睡眠的药物受体拮抗剂。
• IBX-Promoted Oxidative Cyclization of <i>N</i>-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines
  作者：Peng Gao、Huai-Juan Chen、Zi-Jing Bai、Mi-Na Zhao、Desuo Yang、Juan Wang、Ning Wang、Lele Du、Zheng-Hui Guan

  DOI：10.1021/acs.joc.0c00625

  日期：2020.6.19

  An iodoxybenzoic acid-mediated selected oxidative cyclization of N-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alcohol, followed by condensation of aldehyde and α-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally

  开发了碘氧基苯甲酸介导的N-羟烷基烯胺的选择氧化环化。通过这种策略，以良好的选择性生产了各种2,3-二取代的吡咯和吡啶，涉及醇的氧化，然后醛与烯胺的α-C缩合。此外，这种无金属方法具有多个优点，包括使用环保试剂，广泛的底物范围，温和的反应条件和高效率。
• The Guareschi Pyridine Scaffold as a Valuable Platform for the Identification of Selective PI3K Inhibitors
  作者：Ubaldina Galli、Elisa Ciraolo、Alberto Massarotti、Jean Margaria、Giovanni Sorba、Emilio Hirsch、Gian Tron

  DOI：10.3390/molecules200917275

  日期：——

  A novel series of 4-aryl-3-cyano-2-(3-hydroxyphenyl)-6-morpholino-pyridines have been designed as potential phosphatidylinositol-3-kinase (PI3K) inhibitors. The compounds have been synthesized using the Guareschi reaction to prepare the key 4-aryl-3-cyano-2,6-dihydroxypyridine intermediate. A different selectivity according to the nature of the aryl group has been observed. Compound 9b is a selective inhibitor against the PI3Kα isoform, maintaining a good inhibitory activity. Docking studies were also performed in order to rationalize its profile of selectivity.

  设计了一系列新型的4-芳基-3-氰基-2-(3-羟基苯基)-6-吗啉代吡啶作为潜在的磷脂酰肌醇-3-激酶(PI3K)抑制剂。通过Guareschi反应合成了关键的4-芳基-3-氰基-2,6-二羟基吡啶中间体。根据芳基基团的性质，观察到了不同的选择性。化合物9b是针对PI3Kα同工酶的选择性抑制剂，并保持良好的抑制活性。为了合理化其选择性特征，还进行了对接研究。