2-环己基甲基乙酰乙酸乙酯 | 5469-47-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 2-环己基甲基乙酰乙酸乙酯
• 英文名称: ethyl 2-(cyclohexylmethyl)-3-oxobutanoate
• 英文别名: 2-cyclohexylmethyl-acetoacetic acid ethyl ester；2-Cyclohexylmethyl-acetessigsaeure-aethylester；ethyl-2-aceto-3-cyclohexylpropanoate
• CAS: 5469-47-6
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: BHRDSMFTTKGJGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  2-环己基甲基乙酰乙酸乙酯 在 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 [3-(cyclohexylmethyl)-4-methyl-2-oxochromen-7-yl] N,N-dimethylcarbamate
  参考文献：
  名称：

  Discovery and structure–activity relationship of coumarin derivatives as TNF-α inhibitors

  摘要：

  The discovery and structure-activity relationship of a novel series of coumarin-based TNF-alpha inhibitors is described. Starting from the initial lead la, various derivatives were prepared surrounding the coumarin core structure to optimize the in vitro inhibitory activity of TNF-alpha production by human peripheral blood mononuclear cells (hPBMC), stimulated by bacterial lipopolysaccharide (LPS). Selected compounds also demonstrated in vivo inhibition of TNF-alpha production in rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.022
• 作为产物：
  描述：

  (碘甲基)环己烷 、 乙酰乙酸乙酯 在 sodium ethanolate 作用下， 生成 2-环己基甲基乙酰乙酸乙酯
  参考文献：
  名称：

  The Preparation of Some Alkyl Fumaric Acids and Maleic Anhydrides

  摘要：

  DOI：

  10.1021/ja01629a122

文献信息

• Iron-Catalyzed Stereoselective Cross-Coupling Reactions of Stereodefined Enol Carbamates with Grignard Reagents
  作者：Ana Cristina Parra Rivera、Raymond Still、Doug E. Frantz

  DOI：10.1002/anie.201601899

  日期：2016.6.1

  A practical and highly stereoselective iron‐catalyzed cross‐coupling reaction of stereodefined enol carbamates and Grignard reagents to yield tri‐ and tetrasubstituted acrylates is reported. A facile method for the stereoselective generation of these enol carbamates has also been developed.

  报道了一种实用且高度立体选择性的铁催化的立体定义的烯醇氨基甲酸酯和Grignard试剂的交叉偶联反应，生成三和四取代的丙烯酸酯。还开发了用于立体选择性地产生这些烯醇氨基甲酸酯的简便方法。
• Theoretical investigation of the reaction of dialkylzincs with α-alkoxycarbonyl radicals. Evaluation of α-bromoacrylates as radical acceptors in radical-polar crossover processes
  作者：François Vibert、Julien Maury、Hugo Lingua、Eric Besson、Didier Siri、Michèle P. Bertrand、Laurence Feray

  DOI：10.1016/j.tet.2015.09.045

  日期：2015.11

  The evaluation of ethyl α-bromoacrylate as radical acceptor in dialkylzinc radical-polar cascades addresses the question of the parameters controlling homolytic substitution at zinc by α-alcoxycarbonyl radicals. Under non-degassed medium ethyl α-bromoacrylate reacts with diethylzinc to give a bromocyclopropane. The reaction involves successively radical addition, SH2 at zinc, conjugate addition of

  乙基α-bromoacrylate作为自由基受体的二烷基锌中自由基极性级联地址评估所述参数控制在锌通过α-alcoxycarbonyl自由基均裂取代的问题。下与二乙基锌非脱气介质乙基α-bromoacrylate发生反应，得到溴环丙烷。该反应涉及依次基加，S ħ 2在锌，共轭加成所得的烯醇化物与亲电基片和环闭合。理论计算进行以获得更好的洞察详细机制。他们突出锌（II）的螯合的上正式S上的冲击ħ 2步骤。讨论了在其他亲电子试剂（醛和酰基硅烷）存在下进行的其他实验。
• Acylacetate and amidine intermediates for pyrimidone compounds, and their preparation
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0180745A1

  公开（公告）日：1986-05-14

  Compounds of formulae II and III below are useful as intermediates for the preparation of pyrimidones of formula I below which are gastric acid secretion inhibitors and have other medical utilitv: wherein R, represents a hydrogen atom, an alkyl group, a lower alkenyl group, a lower alkinyl group, a phenyl group, a cycloalkylmethyl group, an unsubstituted or substituted aralkyl group, or the group wherein A represents a lower alkylene group and R3 and R. are the same or different lower alkyl groups or combine to form with the adjacent nitrogen atom a piperidine or pyrrolidine ring; R2 represents a hydrogen atom, a lower alkyl group or a trifluoromethyl group; Y represents a heterocyclic group of the formula: or wherein R represents a hydrogen atom or a lower alkyl group; B represents an oxygen atom or a sulfur atom; m represents zero or an integer of 1 to 3; and n represents an integer of 1 to 3.

  下式 II 和 III 的化合物可用作制备下式 I 的嘧啶酮的中间体，下式 I 的嘧啶酮是胃酸分泌抑制剂，并具有其他医疗用途： 其中 R 代表氢原子、烷基、低级烯基、低级烷基、苯基、环烷基甲基、未取代或取代的芳基或基团 其中 A 代表低级亚烷基，R3 和 R. 是相同或不同的低级烷基，或与相邻的氮原子结合形成哌啶或吡咯烷环；R2 代表氢原子、低级烷基或三氟甲基；Y 代表式中的杂环基团： 或 其中 R 代表氢原子或低级烷基；B 代表氧原子或硫原子；m 代表零或 1 至 3 的整数；n 代表 1 至 3 的整数。
• Piperidine derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0506478A1

  公开（公告）日：1992-09-30

  3,4,4-trisubstitutedpiperidinyl-alkyl-carboxylates and intermediates for their preparation are provided. These piperidine-N-alkylcarboxylates are useful as peripheral opioid antagonists.

  提供了 3,4,4-三取代哌啶-N-烷基羧酸盐及其制备中间体。这些哌啶-N-烷基羧酸盐可用作外周阿片拮抗剂。
• [1,2,4]Triazolo[1,5-a]pyrimidine derivatives: Structure-activity relationship study leading to highly selective ENPP1 inhibitors
  作者：Mitsuyasu Kawaguchi、Shohei Minami、Naoya Ieda、Hidehiko Nakagawa

  DOI：10.1016/j.bmcl.2024.129820

  日期：2024.9

  treatment of various infectious diseases and cancers, ENPP1 inhibitors have attracted great attention as candidate drugs. We have previously identified small-molecule ENPP1 inhibitors having a [1,2,4]triazolo[1,5-]pyrimidine scaffold by means of chemical screening using a fluorescence probe, TG-mAMP. In this study, we evaluated the structure–activity relationships of the hit and lead compounds in detail

  STING（干扰素基因刺激剂）途径是调节先天免疫的途径之一，细胞外水解酶外核苷酸焦磷酸酶/磷酸二酯酶1（ENPP1）已被确定为其显性负调节因子。由于激活先天免疫系统是治疗各种传染病和癌症的一种有前景的策略，ENPP1抑制剂作为候选药物引起了极大的关注。我们之前通过使用荧光探针TG-mAMP进行化学筛选，鉴定了具有[1,2,4]三唑并[1,5-]嘧啶支架的小分子ENPP1抑制剂。在这项研究中，我们详细评估了命中化合物和先导化合物的构效关系，并成功开发了不仅能强烈、选择性地抑制 ENPP1 的化合物，而且还能在细胞系统中抑制 ENPP1。