6,8-二氯-3-氰基色酮 | 72798-32-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 6,8-二氯-3-氰基色酮
• 中文别名: 6,8-D二氯-3-氰基色酮；6,8-二氯-4-氧-4H-1-苯并吡喃-3-甲腈
• 英文名称: 6,8-dichloro-4-oxo-4H-1-benzopyran-3-carbonitrile
• 英文别名: 6,8-dichloro-3-cyanochromone；6,8-dichloro-4-oxochromene-3-carbonitrile
• CAS: 72798-32-4
• 化学式: C₁₀H₃Cl₂NO₂
• mdl: MFCD00192004
• 分子量: 240.045
• InChiKey: YERQUFAYRCSXEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  169-174 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  6,8-二氯-3-氰基色酮 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 ethyl 2-(4-aza-6,8-dichloroxanthon-3-yl)acetate
  参考文献：
  名称：

  Efficient synthesis of benzopyrano[2,3-b]pyridines by sequential reactions of 1,3-bis-silyl enol ethers with 3-cyanobenzopyrylium triflates

  摘要：

  Benzopyrano[2,3-b]pyridines were efficiently prepared by condensation of 1,3-bis-silyl enol ethers with 3-cyanobenzopyrylium triflates and Subsequent domino 'retro-Michael-lactonization-aldol' reactions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01030-x
• 作为产物：
  描述：

  6,8-dichloro-4-oxo-4H-1-benzopyran-3-carboxaldehyde 3-O-methyl oxime 在 4 A molecular sieve 、 硫酸 作用下， 以 苯 为溶剂， 以49%的产率得到6,8-二氯-3-氰基色酮
  参考文献：
  名称：

  A Rare Acid-Promoted Elimination of O-Methyl Oximes:  A Practical Synthesis of 3-Cyano-4-benzopyrones

  摘要：

  DOI：

  10.1021/jo991031j

文献信息

• Synthesis of 1-azaxanthones by condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-(cyano)benzopyrylium triflates and subsequent domino ‘retro-Michael/nitrile-addition/heterocyclization’ reaction
  作者：Muhammad A. Rashid、Nasir Rasool、Bettina Appel、Muhammad Adeel、Vahuni Karapetyan、Satenik Mkrtchyan、Helmut Reinke、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2008.02.105

  日期：2008.5

  Functionalized 1-azaxanthones (5-oxo-5H-[1]-benzopyrano[2,3-b]pyridines) were prepared by TMSOTf-mediated condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-cyanochromones and subsequent base-mediated domino ‘retro-Michael/nitrile-addition/heterocyclization’ reaction.

  通过TMSOTf介导的1,3-双（三甲基甲硅烷氧基）-1,3-丁二烯与3的缩合反应制备功能化的1-azaxanthones（5-oxo-5 H- [1]-苯并吡喃并[2,3- b ]吡啶）。 -氰基色酮和随后的碱基介导的多米诺骨牌“复古迈克尔/腈加成/杂环化”反应。
• Ultrasound promoted synthesis of chromeno[2,3-b]pyridines and their evaluation as lipid peroxidation inhibitors
  作者：Eleni Dimitriadou、Marianna Raftopoulou、Paraskevi M. Kasapidou、Constantinos A. Tsoleridis、Julia Stephanidou-Stephanatou、Dimitra J. Hadjipavlou-Litina、Christos Kontogiorgis、Agathi Pritsa、Athanasios Papadopoulos

  DOI：10.3998/ark.5550190.p008.754

  日期：——

  A series of 2,3-disubstituted-5-oxochromeno[2,3-b]pyridine derivatives were synthesized under ultrasound irradiation, and also under conventional methods, from the reaction of 3cyanochromones with some active methylene compounds in the presence of a stoichiometric base. The structures of the products were unambiguously elucidated by 1D and 2D NMR experiments. Full assignment of all H and C NMR chemical

  一系列 2,3-二取代-5-氧代色基 [2,3-b] 吡啶衍生物在超声辐照下合成，也在常规方法下，由 3-氰基色酮与一些活性亚甲基化合物在化学计量碱存在下的反应合成. 通过一维和二维核磁共振实验明确阐明了产物的结构。已实现所有 H 和 C NMR 化学位移的完全分配。此外，还评估了合成的色诺吡啶衍生物的脂质过氧化抑制作用。
• One-Pot Five-Component Synthesis of Spirocyclopenta[<i>b</i>]chromene Derivatives and Their Acid-Catalyzed Rearrangement
  作者：Michael A. Terzidis、Tryfon Zarganes-Tzitzikas、Constantinos Tsimenidis、Julia Stephanidou-Stephanatou、Constantinos A. Tsoleridis、George E. Kostakis

  DOI：10.1021/jo3014947

  日期：2012.10.19

  tert-butylisocyanide or cyclohexylisocyanide and acetylenedicarboxylates, with 3-cyanochromones is described, whereupon spirochromenofuran derivatives 5 or 6 were obtained in good yields. The subsequent acid-catalyzed rearrangement of the isolated 2-imino-spirochromenofurans 5 to 2-amino-spirochromenofurans 7 has also been studied. Rational mechanistic schemes for the formation of compounds 5, 6, and 7 are proposed

  描述了由叔丁基异氰化物或环己基异氰酸酯与乙炔二羧酸酯原位产生的两性离子中间体与3-氰基色酮的反应，从而以良好的产率获得了螺色呋喃呋喃衍生物5或6。还研究了分离的2-亚氨基-吡咯并呋喃并呋喃5到2-氨基-吡咯并呋喃并呋喃7的随后的酸催化重排。理性机械方案为化合物的形成5，6，和7被提议。产物的结构阐明是通过1D和2D NMR实验完成的，并由X射线晶体学分析证实。借助DFT / GIAO计算已明确实现了所有1 H和13 C NMR化学位移的完全分配。
• Penicillins and their antibacterial use
  申请人：Sandoz Ltd.

  公开号：US04320133A1

  公开（公告）日：1982-03-16

  The invention provides novel penicillins and cephalosporins of formula I, ##STR1## methods for their production and their anti-bacterial use.

  本发明提供了公式I的新型青霉素和头孢菌素，以及它们的生产方法和抗菌用途。##STR1##
• Chalcone and its analogs as agents for the inhibition of angiogenesis and related disease states
  申请人：Bowen J. Phillip

  公开号：US20090018167A1

  公开（公告）日：2009-01-15

  The present invention relates to chalcone and chalcone derivatives and analogs which are useful as angiogenesis inhibitors. The present compounds, which are inexpensive to synthesize, exhibit unexpectedly good activity as angiogenesis inhibitors. The present invention also relates to the use of chalcone and its analogs as antitumor/anticancer agents and to treat a number of conditions or disease states in which angiogenesis is a factor, including angiogenic skin diseases such as psoriasis, acne, rosacea, warts, eczema, hemangiomas, lymphangiogenesis, among numerous others, as well as chronic inflammatory disease such as arthritis.

  本发明涉及用作血管生成抑制剂的查尔酮和查尔酮衍生物和类似物。这些廉价合成的化合物表现出意外的良好的血管生成抑制活性。本发明还涉及将查尔酮及其类似物用作抗肿瘤/抗癌剂，并用于治疗许多与血管生成有关的疾病或病态，包括血管生成性皮肤疾病，如银屑病、痤疮、酒渣鼻、疣、湿疹、血管瘤、淋巴管生成等，以及慢性炎症性疾病，如关节炎。