3-Diazo-2,4-oxolandion | 98026-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-Diazo-2,4-oxolandion
• 英文别名: 3-diazofuran-2,4(3H,5H)-dione；3-diazo-2,4-(3H,5H)-furandione；3-diazooxolane-2,4-dione
• CAS: 98026-98-3
• 化学式: C₄H₂N₂O₃
• 分子量: 126.071
• InChiKey: AUBQVSBGLGKIHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Diazo-2,4-oxolandion 生成 3-Oxomethylene-oxetan-2-one
  参考文献：
  名称：

  Infrared spectroscopy of matrix-isolated propadienone

  摘要：

  DOI：

  10.1021/ja00256a060
• 作为产物：
  描述：

  ethyl 2,4-bis(diazo)-3-oxobutyrate 在 硫酸 作用下， 生成 3-Diazo-2,4-oxolandion
  参考文献：
  名称：

  Weygand et al., Zeitschrift fur Naturforschung, 1957, vol. 12b, p. 596

  摘要：

  DOI：

文献信息

• 3,4-diaryl-2-hydroxy-2,5-dihydrofurans as prodrugs to COX-2 inhibitors
  申请人：Merck Frosst Canada, Inc.

  公开号：US05698584A1

  公开（公告）日：1997-12-16

  The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  这项发明涵盖了化合物I的新颖结构，可用于治疗环氧合酶-2介导的疾病。该发明还涵盖了用于治疗环氧合酶-2介导疾病的某些药物组合物，其中包括化合物I。
• (Methylsulfonyl)phenyl-2-(5H)-furanones as COX-2 inhibitors
  申请人：Merck Frosst Canada, Inc.

  公开号：US06020343A1

  公开（公告）日：2000-02-01

  The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  这项发明涵盖了用于治疗环氧合酶-2介导疾病的新型化合物I的公式。该发明还涵盖了用于治疗环氧合酶-2介导疾病的某些药物组合物，包括化合物I的公式。
• Catalytic Undirected Intermolecular C–H Functionalization of Arenes with 3-Diazofuran-2,4-dione: Synthesis of 3-Aryl Tetronic Acids, Vulpinic Acid, Pinastric Acid, and Methyl Isoxerocomate
  作者：Amarender Manchoju、Sunil V. Pansare

  DOI：10.1021/acs.orglett.6b03087

  日期：2016.11.18

  A variety of 3-aryl tetronic acids have been synthesized by an undirected, intermolecular C–H functionalization of arenes with 3-diazofuran-2,4-dione. This methodology featured as a key step in the synthesis of a series of naturally occurring 3-aryl-5-arylidene tetronic acids (pulvinates) from commercially available tetronic acid. Salient features of the pulvinic acid synthesis include a one-step,

  通过使用3-重氮呋喃-2,4-二酮对芳烃进行无方向的CH-H分子间官能化反应，已经合成了多种3-芳基tetronic酸。该方法学是从可商购的tetronic酸合成一系列天然存在的3-芳基-5-芳基亚芳基tetronic酸（pulvinates）的关键步骤。戊酸合成的显着特征包括C5芳基的一步一步立体选择性合成和C3芳基取代基的一步导入。
• Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A–E, G, Q and their analogues
  作者：Amarender Manchoju、Ritesh A. Annadate、Lise Desquien、Sunil V. Pansare

  DOI：10.1039/c8ob01511b

  日期：——

  highly stereoselective aldol condensation of diazotetronic acid with aldehydes to provide 5-arylidene diazotetronates. Subsequent catalytic intermolecular C–H insertion reactions of the arylidene tetronates with arenes provide a series of naturally occurring aspulvinones including aspulvinones C, D and Q which have not been synthesized before. Variation of the aldehyde and the arene components furnishes

  开发了一种模块化合成的aspulvinones A，B，C，D，E，G和最近分离的aspulvinoneQ。该方法的特点是重氮杂环丁酸与醛类具有高度立体选择性的羟醛缩合反应，可提供5-亚芳基重氮杂环戊酸酯。随后的亚芳基四价酸盐与芳烃的催化分子间CH–H插入反应提供了一系列天然存在的aspulvinones，包括以前从未合成过的aspulvinones C，D和Q。醛和芳烃成分的变化提供了aspulvinones的合成类似物。
• The reactions of diazo compounds with lactones. Part 2.† The reaction of cyclic 2-diazo-1,3-dicarbonyl compounds with diketene: benzofuran formation
  作者：Paul V. Murphy、Timothy J. O’Sullivan、Bryan D. Kennedy、Niall W. A. Geraghty

  DOI：10.1039/b001394n

  日期：——

  Cyclic 2-diazo-1,3-dicarbonyl compounds react with diketene in the presence of rhodium(II) salts to give benzofurans as the major isolated products. The formation of intermediate products with exocyclic double bonds which isomerise to benzofurans provides support for the proposed mechanism which involves initial formation of a dioxaspirooctenone by a formal dipolar cycloaddition reaction of a carbenoid to the exocyclic double bond of diketene followed by the loss of carbon dioxide. Acyclic 2-diazo-1,3-dicarbonyl compounds give furans in poor yield.

  环状 2-重氮-1,3-二羰基化合物在铑（II）盐存在下与二酮反应，生成的主要分离产物是苯并呋喃。中间产物的外环双键异构化为苯并呋喃，这为所提出的机理提供了支持，即通过类羰基化合物与二酮烯的外环双键发生形式上的二极环加成反应，最初形成二噁螺辛酮，随后二氧化碳流失。环状 2-重氮-1,3-二羰基化合物生成呋喃的产量很低。

表征谱图