ethyl 2,5-dioxopentanoate | 251942-38-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2,5-dioxopentanoate
• 英文别名: succinaldehydic acid ethyl ester
• CAS: 251942-38-8
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: AZWGLUVBKUYPRH-UHFFFAOYSA-N

物化性质

• 沸点：
  243.3±23.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  ethyl 2,5-dioxopentanoate 在 盐酸 、 溴 、 溶剂黄146 作用下， 以 水 、 甲苯 为溶剂， 反应 2.0h， 生成 ethyl (S)-1-(1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-bromopent-3-yn-2-yl)-4,5-dibromo-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  NHC–Cu-Catalyzed Addition of Propargylboron Reagents to Phosphinoylimines. Enantioselective Synthesis of Trimethylsilyl-Substituted Homoallenylamides and Application to the Synthesis of S-(−)-Cyclooroidin

  摘要：

  A catalytic method for the efficient and enantioselective addition of a 1-trimethylsilyl-substituted allene moiety to phosphinoylimines is presented. Transformations are promoted by 5.0 mol % of a copper complex of an N-heterocyclic carbene in the presence of a propargylboron reagent that can be readily prepared in multigram quantities. Within 10 min of reaction, products are obtained in up to 91% yield, 98% allene (vs propargyl) selectivity, and 98:2 enantiomeric ratio. An assortment of aldimines serve as suitable substrates. The phosphinoyl and silyl groups can be removed efficiently and orthogonally. The silylallene moiety may be transformed to versatile derivatives that are difficult to access via nonsilylated allenes. The special features and utility of the approach are highlighted through a succinct enantioselective synthesis of marine alkaloid S-(-)-cyclooroidin.

  DOI：

  10.1021/ja500373s
• 作为产物：
  描述：

  2-氧代-5-己酸乙酯 在 臭氧 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.55h， 以66%的产率得到ethyl 2,5-dioxopentanoate
  参考文献：
  名称：

  构筑帕劳阿明ABDE四环核的光化学重排

  摘要：

  从商业材料开始，分9步合成了palau'amine的ABDE四环碳核。核心的最显着特征是高应变的反式环戊五环[ c ]吡咯烷，是使用环收缩策略从高应变的反式双环内酰胺衍生物（仅需7个步骤即可获得）高收率获得的。

  DOI：

  10.1021/acs.orglett.8b00819

文献信息

• Bridged indenopyrrolocarbazoles
  申请人：Cephalon, Inc.

  公开号：US06359130B1

  公开（公告）日：2002-03-19

  The present invention is directed to novel fused aryl and heteroaryl bridged indenopyrrolocarbazoles which are useful, inter alia, as therapeutic agents. The invention is also directed to methods for making and using the bridged indenopyrrolocarbazoles.

  本发明涉及新型的融合芳基和杂芳基桥联的茚吡咯咯喹唑，其可用作治疗剂等。该发明还涉及制备和使用这些桥联的茚吡咯咯喹唑的方法。
• Total syntheses of (+)-agelastatin A and (+)-agelastatin B through cationic cyclizations
  作者：Yanmin Yao、Xiaobin Wang、Guangxin Liang

  DOI：10.1016/j.tet.2017.06.009

  日期：2017.8

  We report concise asymmetric total syntheses of tetracyclic marine alkaloids (+)-agelastatin A and (+)-agelastatin B using a cationic cyclization-based approach, which features straightforward transformations with cost-effective chemicals and reagents. (C) 2017 Published by Elsevier Ltd.
• Structures, Reactivities, and Antibiotic Properties of the Marinopyrroles A−F
  作者：Chambers C. Hughes、Christopher A. Kauffman、Paul R. Jensen、William Fenical

  DOI：10.1021/jo1002054

  日期：2010.5.21

  Cultivation of actinomycete strain CNQ-418, retrieved from a deep ocean sediment sample off the coast of La Jolla, CA, has provided marinopyrroles A F. Sharing just 98% 16S rRNA gene sequence identity with S. sannurensis, the strain likely represents a new Streptomyces species. The metabolites contain an unusual 1,3'-bipyrrole core decorated with several chlorine and bromine substituents and possess marked antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The congested N,C-biaryl bond establishes an axis of chirality that, for marinopyrroles A-E, is configurationally stable at room temperature. Moreover, the natural products are fashioned strictly in the M-configuration. The Paal-Knorr condensation was adapted for the synthesis of the 1,3'-bipyrrole core. Halogenation of this material with N-bromosuccinimide cleanly furnished the 4,4',5,5'-tetrahalogenated core that characterizes this class of marine-derived metabolites.
• MODULATING MULTIPLE LINEAGE KINASE PROTEINS
  申请人：CEPHALON, INC.

  公开号：EP1105728B1

  公开（公告）日：2005-04-13
• BRIDGED INDENOPYRROLOCARBAZOLES
  申请人：CEPHALON, INC.

  公开号：EP1083903A1

  公开（公告）日：2001-03-21