2,3-二乙炔基喹喔啉 | 98813-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2,3-二乙炔基喹喔啉
• 英文名称: 2,3-diethynylquinoxaline
• 英文别名: 2,3-Diethynyl quinoxaline
• CAS: 98813-72-0
• 化学式: C₁₂H₆N₂
• 分子量: 178.193
• InChiKey: HRPSROGUYINECB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,3-二乙炔基喹喔啉 在 四氯化碳 作用下， 生成 1,4-dichlorophenazine
  参考文献：
  名称：

  Rapid Bergman Cyclization of 1,2-Diethynylheteroarenes

  摘要：

  The synthesis and cyclization of acyclic quinoxaline, pyridine, and pyrimidine enediynes (1-3) are described. These compounds were prepared using palladium(0) coupling of trimethylsilyl acetylene to o-dihalo- or o-halotriflic heteroarenes. All compounds were prepared in modest to good yields. The enediynes prepared were shown to undergo Bergman cyclization. Kinetics over a minimum of 3 half-lives were used to construct Arrhenius plots. Pyrimidine 3 was found to have an activation energy of 16.1 kcal/mol. Cyclization of the closest known aromatic analogue, o-diethynylbenzene (15), has E-a = 25.1 kcal/mol (Grissom, J. W.; Calkins, T. L.;McMillen, H. A.; Jiang, Y. J. Org. Chem. 1994, 59, 5833-5835). Pyridine 2 and quinoxaline 1 gave activation energies of 21.5 and 33.6 kcal/mol, respectively. The results illustrate that heteroarenes can be used to activate Bergman cyclization. We expect these compounds to play an important role in furthering the understanding of Bergman cyclization and in aiding the development of new biologically significant enediynes.

  DOI：

  10.1021/jo980879p
• 作为产物：
  描述：

  2,3-bis(3-hydroxy-3-methylbut-1-ynyl)quinoxaline 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以65%的产率得到2,3-二乙炔基喹喔啉
  参考文献：
  名称：

  Ames, Donald E.; Mitchell, John C.; Takundwa, Chisango C., Journal of Chemical Research, Miniprint, 1985, # 5, p. 1683 - 1696

  摘要：

  DOI：

文献信息

• 1,3-Dipolar cycloaddition of azomethine imines to ethynyl hetarenes: A synthetic route to 2,3-dihydropyrazolo[1,2- a ]pyrazol-1(5 H )-one based heterobiaryls
  作者：Julia I. Nelina-Nemtseva、Anna V. Gulevskaya、Vitaliy V. Suslonov、Alexander D. Misharev

  DOI：10.1016/j.tet.2018.01.046

  日期：2018.3

  π-Deficient ethynyl hetarenes were used as dipolarophiles in a 1,3-dipolar cycloaddition reaction with azomethine imines (2-arylidene-5-oxopyrazolidin-2-ium-1-ides). Both CuI-catalyzed and catalyst-free thermally induced reactions proceeded with high regioselectivity providing 6-hetaryl-5-aryl-2,3-dihydropyrazolo[1,2-a]pyrazol-1(5H)-ones in moderate to excellent yields. The ethynyl hetarenes (pyridines

  在与偶氮甲亚胺（1,2-亚芳基-5-氧并吡唑并丁-2-盐-1-化物）进行的1,3-偶极环加成反应中，将π缺乏的乙炔基戊烯用作偶极亲和剂。CuI催化的和无催化剂的热诱导反应均以高区域选择性进行，从而以中等至优异的产率提供了6-杂芳基-5-芳基-2,3-二氢吡唑并[1,2- a ]吡唑-1（5 H）-一。 。乙炔基戊烯（吡啶，吡嗪，喹喔啉，蝶啶和嘧啶[4,5- c ]哒嗪）与邻甲基，邻氰基和邻甲基-炔基取代基适用于该反应。炔基戊烯与偶氮甲亚胺或其他1,3-偶极试剂的1,3-偶极环加成反应可以被视为杂二芳基化合物的另一种合成方法。
• One-step synthesis of dialkynyl-1,2-diones and their conversion to fused pyrazines bearing enediyne units
  作者：Rüdiger Faust、Christian Weber、Vito Fiandanese、Giuseppe Marchese、Angela Punzi

  DOI：10.1016/s0040-4020(97)01007-7

  日期：1997.10

  and oxalyl chloride in the presence of CuBr and LiBr is described. The condensation of 3 with various aromatic and heteroaromatic 1,2-diamines leads to pyrazine-based α-dialkynylated heterocycles. The enediyne substructure of diethynylquinoxaline can be thermally rearranged in a Bergman cyclization reaction.

  描述了在CuBr和LiBr存在下由乙炔锂和草酰氯制备对称的末端保护的二炔基1,2-二酮3的简便方法。3与各种芳族和杂芳族1,2-二胺的缩合导致形成吡嗪基α-二炔基化杂环。二乙炔基喹喔啉的烯二炔亚结构可以在Bergman环化反应中进行热重排。
• POLYMER COMPOSITION
  申请人：Nilsson Daniel

  公开号：US20110315424A1

  公开（公告）日：2011-12-29

  The invention relates to a method for modifying a polymer composition, to modified polymer compositions, to an article, preferably wire or cable, comprising said modified polymer composition, to a process for preparing an article, preferably a wire or cable, to the use of said modified polymer in one or more layers of a wire or cable, as well as to a compound for use as a radical generating compound for modifying a polymer composition.

  本发明涉及一种改性聚合物组合物的方法，改性聚合物组合物，一种物品，优选为包括改性聚合物组合物的电线或电缆，制备物品的方法，优选为制备电线或电缆，将改性聚合物用于电线或电缆的一层或多层的用途，以及一种用作改性聚合物组合物的自由基产生化合物。
• Solvent dependent bergman cyclization of 2,3-diethynylquinoxaline
  作者：Chang-Sik Kim、K.C. Russell

  DOI：10.1016/s0040-4039(99)00634-6

  日期：1999.5

  Kinetics of thermocyclization of 2,3-diethynylquinoxaline have been studied in various solvents. The cyclization rates observed were surprisingly solvent dependent. The half-lives varied from 361 in CH3CN to 16 min in THF. The half-life data show a good correlation with the solvents' spectroscopic E-T(30) values and dielectric constants. (C) 1999 Elsevier Science Ltd. All rights reserved.
• AMES, D. E.;MITCHELL, J. C.;TAKUNDWA, CH. C., J. CHEM. RES. SYNOP., 1985, N 5, 144-145
  作者：AMES, D. E.、MITCHELL, J. C.、TAKUNDWA, CH. C.

  DOI：——

  日期：——