4-乙烯基-4-甲基环己-2-烯-1-酮 | 114300-64-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙烯基-4-甲基环己-2-烯-1-酮
• 英文名称: (±)4-methyl-4-vinylcyclohex-2-enone
• 英文别名: 4-methyl-4-vinylcyclohex-2-enone；2-Cyclohexen-1-one, 4-ethenyl-4-methyl-；4-ethenyl-4-methylcyclohex-2-en-1-one
• CAS: 114300-64-0
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: OVFWPWSMANSTRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-乙烯基-4-甲基环己-2-烯-1-酮 以17%的产率得到
  参考文献：
  名称：

  MARX, JOHN N.;HAHN, YOUNG-SOOK PAIK, J. ORG. CHEM., 53,(1988) N 12, 2866-2868

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Methyl-cyclohexen-(2)-carbonsaeure-aethylester 在 selenium(IV) oxide 作用下， 生成 4-乙烯基-4-甲基环己-2-烯-1-酮
  参考文献：
  名称：

  Sharma,S.D. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15, p. 958 - 959

  摘要：

  DOI：

文献信息

• [EN] MONOCYCLIC CYANOENONES AND METHODS OF USE THEREOF<br/>[FR] CYANOÉNONES MONOCYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：DARTMOUTH COLLEGE

  公开号：WO2010011782A1

  公开（公告）日：2010-01-28

  The present invention features monocyclic cyanoenone compositions and methods for using the same in the treatment of diseases such as cancer, inflammatory diseases and neurodegenerative diseases.

  本发明涉及单环氰基烯酮组合物及其在治疗癌症、炎症性疾病和神经退行性疾病等疾病中的应用方法。
• MONOCYCLIC CYANOENONES AND METHODS OF USE THEREOF
  申请人：Honda Tadashi

  公开号：US20110196007A1

  公开（公告）日：2011-08-11

  The present invention features monocyclic cyanoenone compositions and methods for using the same in the treatment of diseases such as cancer, inflammatory diseases and neurodegenerative diseases.

  本发明涉及单环氰基烯酮组合物及其在治疗癌症、炎症性疾病和神经退行性疾病等疾病中的应用方法。
• Chemoenzymatic Late‐Stage Modifications Enable Downstream Click‐Mediated Fluorescent Tagging of Peptides
  作者：Alessandro Colombano、Luca Dalponte、Sergio Dall'Angelo、Claudia Clemente、Mohannad Idress、Ahmad Ghazal、Wael E. Houssen

  DOI：10.1002/anie.202215979

  日期：——

  suitable for copper-catalyzed azide-alkyne cycloaddition, metathesis, and inverse-electron-demand Diels-Alder (IEDDA) reactions. A 10-mer tryptophan-containing macrocyclic peptide was tailored by AcyF, and the resulting modified peptide was successfully labelled with a tetrazine–fluorescein conjugate by IEDDA.

  用 22 种非天然焦磷酸盐筛选了 N1-色氨酸异戊二烯基转移酶 AcyF 的混杂性，这些焦磷酸盐表现出适合铜催化叠氮-炔环加成、复分解和逆电子需求 Diels-Alder (IEDDA) 反应的反应基团。 AcyF 定制了含有色氨酸的 10 聚体大环肽，并通过 IEDDA 成功地用四嗪-荧光素缀合物标记了所得修饰肽。
• Vinyltriarylbismuthonium Salts: Powerful Vehicles for α-Vinylation of Carbonyl Compounds
  作者：Li Li、Lingbowei Hu、Jirapon Sae-Jew、Viresh H. Rawal

  DOI：10.1021/jacs.4c05709

  日期：2024.7.10

  to the formation of α-vinylated carbonyl compounds in good to excellent yields and with a remarkably broad substrate scope. Critically, this vinylation method is effective for enolates generated via numerous methods, enabling the sequencing of reactions that generate enolates with the vinylation step and the ready synthesis of diversely functionalized compounds, thereby underscoring the versatility and

  α-乙烯基-羰基化合物是一类正交官能化分子，其中固有的 C=O 和 C=C 键可用于解锁明显不同的反应性。在本报告中，我们提出了一种利用乙烯基三芳基铋鎓（“乙烯基-Bis”）盐直接对羰基化合物进行α-乙烯基化的简单方法，该盐稳定且易于在十克规模上制备。这种转化是通过原位生成的烯醇锂中间体与乙烯基双试剂的反应有效完成的，从而以良好至优异的产率和非常广泛的底物范围形成α-乙烯基化羰基化合物。至关重要的是，这种乙烯基化方法对于通过多种方法生成的烯醇化物是有效的，能够对通过乙烯基化步骤生成烯醇化物的反应进行排序，并易于合成不同官能化的化合物，从而强调了该方法的多功能性和实用性。还证明了离散的烯醇化物与其他乙烯基单元和芳基的类似反应。
• Synthesis, Chemical Reactivity as Michael Acceptors, and Biological Potency of Monocyclic Cyanoenones, Novel and Highly Potent Anti-inflammatory and Cytoprotective Agents
  作者：Suqing Zheng、Y. R. Santosh Laxmi、Emilie David、Albena T. Dinkova-Kostova、Katherine H. Shiavoni、Yanqing Ren、Ying Zheng、Isaac Trevino、Ronald Bumeister、Iwao Ojima、W. Christian Wigley、James B. Bliska、Dale F. Mierke、Tadashi Honda

  DOI：10.1021/jm3003922

  日期：2012.5.24

  Novel monocyclic cyanoenones examined to date display unique features regarding chemical reactivity as Michael acceptors and biological potency. Remarkably, in some biological assays, the simple structure is more potent than pentacyclic triterpenoids (e.g., CDDO and bardoxolone methyl) and tricycles (e.g., TBE-31). Among monocyclic cyanoenones, 1 is a highly reactive Michael acceptor with thiol nucleophiles. Furthermore, an important feature of 1 is that its Michael addition is reversible. For the inhibition of NO production, 1 shows the highest potency. Notably, its potency is about three times higher than CDDO, whose methyl ester (bardoxolone methyl) is presently in phase III clinical trials. For the induction of NQO1, 1 also demonstrated the highest potency. These results suggest that the reactivity of these Michael acceptors is closely related to their biological potency. Interestingly, in LPS-stimulated macrophages, 1 causes apoptosis and inhibits secretion of TNF-alpha and IL-1 beta with potencies that are higher than those of bardoxolone methyl and TBE-31.