tert-butyl 2-acetyl-4-oxopentanoate | 318511-70-5

• 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
• 英文名称: tert-butyl 2-acetyl-4-oxopentanoate
• 英文别名: Tert-butyl 2-acetyl-4-oxopentanoate
• CAS: 318511-70-5
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: CHAMKNSLGLXNAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-acetyl-4-oxopentanoate 在 硫酸 作用下， 反应 8.0h， 以90.9%的产率得到2,5-己二酮
  参考文献：
  名称：

  一种2，5-己二酮的合成方法

  摘要：

  本发明提供了一种2，5‑己二酮的合成方法，采用乙酰乙酸叔丁酯在碱的作用下与氯丙酮反应生成3‑乙酰甲基乙酰乙酸叔丁酯，然后在酸性条件下水解，脱酸得到2，5‑己二酮。本发明的有益效果：技术成本低，原材料容易获得，产率高。

  公开号：

  CN110845333A
• 作为产物：
  描述：

  乙酰乙酸叔丁酯 、 溴丙酮 在 sodium ethanolate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 4.25h， 以70.1%的产率得到tert-butyl 2-acetyl-4-oxopentanoate
  参考文献：
  名称：

  高强度小分子肽偶联物作为新型HIV-1融合抑制剂的设计，合成和生物学评估

  摘要：

  小分子融合抑制剂N-（4-羧基-3-羟基苯基）-2,5-二甲基吡咯（NB-2）和N-（3-羧基-4-羟基苯基）-2,5-二甲基吡咯（A 12）靶HIV-1 gp41的疏水口袋，并具有中等的抗HIV-1活性。在本文中，我们报道了一组杂合分子的设计，合成和结构-活性关系，其中C34肽的口袋结合结构域区段被NB-2和A 12取代衍生品。此外，分析了小分子与肽部分之间的协同作用，并发现了具有新型支架的先导化合物。我们发现单独的非肽或肽部分对HIV-1介导的细胞间融合均显示弱活性，但结合物正确地产生了强大的协同作用。其中，缀合物Aoc-βAla-P26和Noc-βAla-P26在细胞-细胞融合测定中显示出低的纳摩尔IC 50值，并有效抑制了对T20敏感和耐药的HIV-1菌株。此外，新分子对蛋白酶K的消化表现出比T20和C34更好的稳定性。

  DOI：

  10.1021/jm3018964

文献信息

• Tandem homologation-acylation chemistry: Single and double homologation
  作者：Carley S. Henderson、Jennifer R. Mazzone、Amanda M. Moore、Charles K. Zercher

  DOI：10.1016/j.tet.2021.132223

  日期：2021.7

  Furakawa-variant of the Simmons-Smith reagent results in homologation and production of an intermediate zinc enolate. Treatment of the enolate with various acylating agents generate products with both γ-dicarbonyl functionality and β−dicarbonyl functionality. In situ exposure of the acylated product to additional zinc carbenoid effects a second regiospecific homologation reaction.

  用 Simmons-Smith 试剂的 Furakawa 变体处理 β-二羰基会导致同系化并产生中间体烯醇锌。用各种酰化剂处理烯醇化物生成具有γ-二羰基官能团和β-二羰基官能团的产物。将酰化产物原位暴露于额外的类胡萝卜素锌会引起第二个区域特异性同系反应。
• Asymmetric Synthesis of Highly Substituted β-Lactones through Oxidative Carbene Catalysis with LiCl as Cooperative Lewis Acid
  作者：Srikrishna Bera、Ramesh C. Samanta、Constantin G. Daniliuc、Armido Studer

  DOI：10.1002/anie.201405200

  日期：2014.9.1

  The reaction of enals with β‐diketones, β‐ketoesters, and malonates bearing a β‐oxyalkyl substituent at the α‐position by oxidative NHC catalysis to provide highly substituted β‐lactones is described. Reactions occur with excellent diastereo‐ and enantioselectivity. The organo cascade comprises two CC bond formations and one CO bond formation. Up to four contiguous stereogenic centers including two

  描述了通过氧化NHC催化烯类与在α位带有β-氧烷基取代基的β-二酮，β-酮酸酯和丙二酸酯的反应，以提供高度取代的β-内酯。反应发生时具有极佳的非对映异构和对映选择性。所述有机级联包括两个C  C键的形成和一种C  O键的形成。级联中最多形成四个连续的立体中心，包括两个完全取代的立体中心。
• Total Synthesis of Catunaregin and Preliminary Evaluation of Its Antitumor Activity
  作者：Hideki Abe、Takuma Hikichi、Kosuke Emori、Akihito Yokosuka、Yoshihiro Mimaki、Toyoharu Kobayashi、Hisanaka Ito

  DOI：10.1002/ejoc.201800219

  日期：2018.4.17

  The total synthesis of catunaregin in both racemic and optically active forms was accomplished. The enantioselective synthesis uses the Evans aldol strategy, with an oxazolidinone or thiazolidinethione as the chiral auxiliary. The key features include a syn‐selective aldol reaction to form the Evans‐syn or non‐Evans‐syn product, and a successive ketalization reaction of a furanyl diol derivative under

  Catunaregin的外消旋和旋光活性形式都可以完全合成。对映选择性合成使用Evans aldol策略，并以恶唑烷酮或噻唑烷硫酮为手性助剂。主要功能包括形成Evans- syn或非Evans- syn产物的顺-选择性羟醛反应，以及在酸性条件下呋喃二醇衍生物的连续缩酮化反应。
• Screening of a Custom-Designed Acid Fragment Library Identifies 1-Phenylpyrroles and 1-Phenylpyrrolidines as Inhibitors of Notum Carboxylesterase Activity
  作者：William Mahy、Mikesh Patel、David Steadman、Hannah L. Woodward、Benjamin N. Atkinson、Fredrik Svensson、Nicky J. Willis、Alister Flint、Dimitra Papatheodorou、Yuguang Zhao、Luca Vecchia、Reinis R. Ruza、James Hillier、Sarah Frew、Amy Monaghan、Artur Costa、Magda Bictash、Magnus W. Walter、E. Yvonne Jones、Paul V. Fish

  DOI：10.1021/acs.jmedchem.0c00660

  日期：2020.9.10

  The Wnt family of proteins are secreted signaling proteins that play key roles in regulating cellular functions. Recently, carboxylesterase Notum was shown to act as a negative regulator of Wnt signaling by mediating the removal of an essential palmitoleate. Here we disclose two new chemical scaffolds that inhibit Notum enzymatic activity. Our approach was to create a fragment library of 250 acids for screening against Notum in a biochemical assay followed by structure determination by X-ray crystallography. Twenty fragments were identified as hits for Notum inhibition, and 14 of these fragments were shown to bind in the palmitoleate pocket of Notum. Optimization of 1-phenylpyrrole 20, guided by structure-based drug design, identified 20z as the most potent compound from this series. Similarly, the optimization of 1-phenylpyrrolidine 8 gave acid 26. This work demonstrates that inhibition of Notum activity can be achieved by small, drug-like molecules possessing favorable in vitro ADME profiles.
• What Happens to the State in Conflict?: Political Analysis as a Tool for Planning Humanitarian Assistance
  作者：Lionel Cliffe、Robin Luckham

  DOI：10.1111/1467-7717.00150

  日期：2000.12

  It is now part of received wisdom that humanitarian assistance in conflict and post‐conflict situations may be ineffective or even counterproductive in the absence of an informed understanding of the broader political context in which so‐called ‘complex political emergencies’ (CPEs) occur. Though recognising that specific cases have to be understood in their own terms, this article offers a framework for incorporating political analysis in policy design. It is based on a programme of research on a number of countries in Africa and Asia over the last four years. It argues that the starting‐point should be an analysis of crises of authority within contemporary nation‐states which convert conflict (a feature of all political systems) into violent conflict; of how such conflict may in turn generate more problems for, or even destroy, the state; of the deep‐rooted political, institutional and developmental legacies of political violence; and of the difficulties that complicate the restoration of legitimate and effective systems of governance after the ‘termination’ of conflict. It then lists a series of questions which such an analysis would need to ask — less in order to provide a comprehensive check‐list than to uncover underlying political processes and links. It is hoped these may be used not only to understand the political dynamics of emergencies, but also to identify what kinds of policy action should and should not be given priority by practitioners.