6-氟色酮-3-腈 | 227202-21-3

• 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-氟色酮-3-腈
• 中文别名: 6-氟-4-氧代-4H-亚甲基-3-甲腈
• 英文名称: 6-fluoro-4-oxo-4H-1-benzopyran-3-carbonitrile
• 英文别名: 6-fluoro-3-cyanochromone；6-fluoro-4-oxo-4H-chromene-3-carbonitrile；3-Cyano-6-fluorochromone；6-fluoro-4-oxochromene-3-carbonitrile
• CAS: 227202-21-3
• 化学式: C₁₀H₄FNO₂
• mdl: MFCD03094001
• 分子量: 189.146
• InChiKey: FUKHLJHJAQNLJO-UHFFFAOYSA-N

物化性质

• 熔点：
  174-178 °C(lit.)
• 沸点：
  288.7±40.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 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：
  4

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  1-ethoxy-2-fluoro-1,3-bis(trimethylsilyloxy)-1,3-butadiene 、 6-氟色酮-3-腈 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以33%的产率得到ethyl 2-fluoro-2-(7-fluoro-5-oxo-5H-chromeno[2,3-b]pyridin-2-yl)acetate
  参考文献：
  名称：

  Synthesis of Highly Functionalized Biaryls by Condensation of 2-Fluoro-1,3-bis(silyloxy) 1,3-Dienes with 3-Cyanochromones and Subsequent Domino “Retro-Michael/Aldol/Fragmentation”

  摘要：

  The Me3SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1,3-bis(trimethylsilyloxy) 1,3-dienes with 3-cyanochromones afforded 3-cyano-2-(4-ethoxy-3-fluoro-2,4-dioxobutyl)-chroman-4-ones. Their reaction with triethylamine afforded fluorinated azaxanthones or biaryls. The product distribution depends on the structure of the diene. The formation of the biaryls can be explained by an unprecedented domino "retro-Michael/aldol/fragmentation" reaction.

  DOI：

  10.1021/jo1018443
• 作为产物：
  描述：

  6-fluoro-4-oxo-4H-1-benzopyran-3-carboxaldehyde 3-O-methyl oxime 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以57%的产率得到6-氟色酮-3-腈
  参考文献：
  名称：

  Synthesis of dihydroxanthone derivatives and evaluation of their inhibitory activity against acetylcholinesterase: Unique structural analogs of tacrine based on the BCD-ring of arisugacin

  摘要：

  A general approach to synthesis of dihydroxanthone derivatives is described here. In vitro evaluation of these dihydroxanthones demonstrated that some derivatives possess moderate anti-cholinesterase activities and better selectivities than tacrine for acetylcholinesterase over butyrylcholinesterase. Structural effects on anti-cholinesterase activities were also examined, and docking experiments were carried out to provide preliminary understandings of these experimental observations. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00115-8

文献信息

• Metal-free access to 3-allyl-2-alkoxychromanones <i>via</i> phosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols
  作者：Ling Meng、Xiaoyong Chang、Zhenyang Lin、Jun (Joelle) Wang

  DOI：10.1039/d1ob00215e

  日期：——

  A phosphine-catalyzed alkoxy allylation of chromones with MBH carbonates and alcohols is established for the metal-free synthesis of 3-allyl-2-alkoxychromanones with high diastereoselectivity.

  一种磷膦催化的MBH碳酸酯和醇与香豆素的烯丙基化反应被建立，用于无金属合成高对映选择性的3-烯丙基-2-烷氧基香豆酮。
• Palladium catalyzed three component coupling reaction between chromones, alcohols, and allylic acetates: diversity-oriented synthesis of highly substituted chromones
  作者：Nitin T. Patil、Zhibao Huo、Yoshinori Yamamoto

  DOI：10.1016/j.tet.2007.02.110

  日期：2007.6

  This paper describes the palladium catalyzed highly efficient three component coupling (TCC) reactions between chromones, allylic acetates, and alcohols, which lead to a library of multiply substituted chromones. The activity of various palladium catalysts, such as Pd(PPh3)4 and Pd2dba3·CHCl3 and their combination with various bisphosphine ligands, was investigated by using THF as a solvent, which

  本文介绍了色酮，烯丙基乙酸酯和醇之间的钯催化高效三组分偶联（TCC）反应，从而形成了一个多取代色酮库。以THF为溶剂，研究了Pd（PPh 3）4和Pd 2 dba 3 ·CHCl 3等钯催化剂及其与各种双膦配体的结合活性，发现Pd（PPh 3）4催化剂是最好的催化剂。该反应最有可能通过在钯催化剂的存在下苯并吡啶鎓阳离子的形成而进行，苯并吡啶鎓阳离子是由色酮与乙酸烯丙酯之间的反应产生的。随后被醇捕获的苯并吡啶鎓阳离子将以优异的产率得到相应的产物。该烷氧基-烯丙基化反应是高度非对映选择性的，并且在所有情况下仅获得一种非对映异构体。
• Asymmetric Roadmap to Diverse Polycyclic Benzopyrans via Phosphine-Catalyzed Enantioselective [4 + 2]-Annulation Reaction
  作者：Adithi Danda、Naredla Kesava-Reddy、Christopher Golz、Carsten Strohmann、Kamal Kumar

  DOI：10.1021/acs.orglett.6b01030

  日期：2016.6.3

  addition of the amino acid derived bifunctional N-acylaminophosphine to an α-substituted allene ester generated a zwitterionic dipole that engaged the vinylogous ester function of 3-cyano-chromones in a [4 + 2] annulation reaction to deliver tetrahydroxanthones embodying three consecutive chiral centers in high yields and with excellent enantioselectivities. The established asymmetric synthesis further paves

  将氨基酸衍生的双官能N-酰基氨基膦催化添加到α-取代的烯丙基酯中，生成两性离子偶极，该两性离子偶合了3-氰基色酮的乙烯基酯官能团，并以[4 + 2]的环化反应提供了四氢氧杂蒽，四氢氧杂蒽具有三个连续的手性中心，收率高，对映选择性好。已建立的不对称合成通过有效的级联反应进一步为两类不同的，富含sp 3的四环苯并吡喃类化合物铺平了道路。
• Silver(I)-Catalyzed Enantioselective [3+2]-Cycloaddition Reaction of α-Silylimines: A Facile Route to Quaternary-Carbon-Rich Scaffolds
  作者：Naredla Kesava-Reddy、Christopher Golz、Carsten Strohmann、Kamal Kumar

  DOI：10.1002/chem.201604793

  日期：2016.12.19

  A silver‐catalyzed highly enantioselective 1,3‐dipolar cycloaddition reaction of α‐silylimines with pyrone‐based trisubstituted olefins was developed affording bi‐ and tricyclic α‐quaternary‐carbon‐rich pyrano‐pyrrolidines in excellent yields. The tricyclic benzopyrone adducts thus obtained were efficiently transformed into highly complex tetracyclic scaffolds supporting four consecutive stereogenic

  已开发出一种银催化的α-甲硅烷基苯胺与吡喃基三取代烯烃的高对映选择性1,3-偶极环加成反应，从而以优异的收率提供了双环和三环的富含α-季碳的吡喃吡咯烷。由此获得的三环苯并吡喃酮加合物被有效地转化为高度复杂的四环支架，该支架支撑具有四个季碳的四个连续的立体异构中心。
• Pd-Catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates with 3-cyanochromones
  作者：Ijaz Khan、Can Zhao、Yong Jian Zhang

  DOI：10.1039/c8cc02456a

  日期：——

  of vinylethylene carbonates with 3-cyanochromones. By using a palladium complex generated in situ from [Pd2(dba)3]·CHCl3 and phosphoramidite L3 as a catalyst under mild reaction conditions, the process afforded furanobenzodihydropyrans bearing vicinal quaternary stereocenters in high yields with good to high enantio- and diastereoselectivities.

  通过钯催化碳酸亚乙烯酯与3-氰基色酮的不对称脱羧环加成反应，开发了一种构造呋喃基苯并二氢吡喃骨架的有效方法。通过在温和的反应条件下使用由[Pd 2（dba）3 ]·CHCl 3和亚磷酰胺L3原位生成的钯配合物作为催化剂，该方法可以高产率地得到具有邻位季铵立体中心的呋喃并苯并二氢吡喃，对映选择性和非对映选择性都很高。 。