2-phenylthieno<2,3-b>quinoxaline | 75163-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-phenylthieno<2,3-b>quinoxaline
• 英文别名: 2-phenylthieno[2,3-b]quinoxaline；2-phenylthieno[3,2-b]quinoxaline
• CAS: 75163-81-4
• 化学式: C₁₆H₁₀N₂S
• 分子量: 262.335
• InChiKey: PIHPBIAOMDHECY-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C(Solv: ethanol (64-17-5))
• 沸点：
  483.0±40.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-phenylthieno<2,3-b>quinoxaline 在 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到4,9-Diacetyl-4,9-dihydro-2-phenylthieno<2,3-b>quinoxaline
  参考文献：
  名称：

  Electrochemical and chemical reduction of furopyrazines, thienopyrazines, furoquinoxalines and thienoquinoxalines

  摘要：

  The electrochemical reduction of furopyrazines, thienopyrazines, furoquinoxalines, and thienoquinoxalines was investigated in protic and aprotic mediums. The thieno[2,3-b]pyrazines and the thieno[3,4-b]pyrazines both lead, in aqueous medium, to a dihydro compound where the two nitrogen atoms of the pyrazine ring are hydrogenated. These primary reduction products isomerize in different ways: in the [2,3-b] series the thiophene ring is reduced while in the [3,4-b] series the pyrazine ring is reduced. These results can be rationalized on the basis of quantum calculations of the energies of the different isomers. These calculations also permit the explanation of the different reducibility between the two series of compounds.

  DOI：

  10.1021/jo00016a008
• 作为产物：
  描述：

  3-(α,β-dibromo-phenethyl)-1H-quinoxalin-2-one 在 diphosphorus pentasulfide 作用下， 以 吡啶 为溶剂， 反应 6.0h， 以12%的产率得到2-phenylthieno<2,3-b>quinoxaline
  参考文献：
  名称：

  Ibrahim, Yehia A.; Badawy, M. A.; El-Bahaie, S., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 699 - 700

  摘要：

  DOI：

文献信息

• NaSH in the construction of thiophene ring fused with N-heterocycles: A rapid and inexpensive synthesis of novel small molecules as potential inducers of apoptosis
  作者：Sunder Kumar Kolli、Ali Nakhi、Raghavender Medishetti、Swapna Yellanki、Pushkar Kulkarni、R. Ramesh Raju、Manojit Pal

  DOI：10.1016/j.bmcl.2014.07.096

  日期：2014.9

  A facile construction of a thiophene ring fused with N-heterocycles has been achieved via the reaction of NaSH with 2-chloro-3-alkynyl quinoxalines/pyrazines leading to novel 2-substituted thieno[2,3-b]pyrazine/quinoxaline derivatives as potential inducers of apoptosis. Some of them showed encouraging pharmacological properties when tested in zebrafish.

  通过NaSH与2-氯-3-炔基喹喔啉/吡嗪反应，可轻松合成与N-杂环稠合的噻吩环，从而生成新的2-取代的噻吩并[2,3- b ]吡嗪/喹喔啉衍生物，潜在的细胞凋亡诱导剂。其中一些在斑马鱼中测试时显示出令人鼓舞的药理特性。
• Synthesis and photophysical properties of selenopheno[2,3-<i>b</i>]quinoxaline and selenopheno[2,3-<i>b</i>]pyrazine heteroacenes
  作者：Amol D. Sonawane、Atsushi Shimozuma、Taro Udagawa、Masayuki Ninomiya、Mamoru Koketsu

  DOI：10.1039/d0ob00718h

  日期：——

  In this paper, we report the novel synthesis of three different heterocycles, namely 2-arylselenopheno[2,3-b]quinoxaline, 3-(aryl/alkylselanyl)-2-arylselenopheno[2,3-b]quinoxaline and 6-phenyl-7-(arylselanyl)selenopheno[2,3-b]pyrazine derivatives, from the corresponding 2,3-dichloroquinoxaline and 2,3-dichloropyrazine derivatives. Furthermore, photophysical properties were investigated to study the

  在本文中，我们报告了三种不同杂环的新颖合成，即2-芳基硒代苯并[2,3- b ]喹喔啉，3-（芳基/烷基硒基）-2-芳基硒代苯并[2,3- b ]喹喔啉和6-苯基来自相应的2,3-二氯喹喔啉和2,3-二氯吡嗪衍生物的-7-（芳基杂戊基）硒代苯并[2,3- b ]吡嗪衍生物。此外，研究了光物理性质以研究杂原子对紫外线吸收和荧光性质的影响。
• Synthesis of thieno[2,3-b]quinoxalines from 2-haloquinoxalines
  作者：Montserrat Armengol、John A. Joule

  DOI：10.1039/b008459j

  日期：——

  The palladium(0)-catalysed coupling of 2-haloquinoxalines with alkynes, addition of one mol equivalent of bromine to the 2-alkynylquinoxalines thus produced and then reaction of the resulting dibromides with dipotassium trithiocarbonate produces thieno[2,3-b]quinoxalines.

  通过钯（0）催化 2-卤代喹喔啉与炔烃的偶联，在生成的 2-炔基喹喔啉中加入一摩尔当量的溴，然后将生成的二溴化物与三硫代碳酸二钾反应，生成噻吩并[2,3-b]喹喔啉。
• Ames, Donald E.; Mitchell, John C.; Takundwa, Chisango C., Journal of Chemical Research, Miniprint, 1985, # 5, p. 1683 - 1696
  作者：Ames, Donald E.、Mitchell, John C.、Takundwa, Chisango C.

  DOI：——

  日期：——
• Ames, Donald E.; Brohi, M. Ismail, Journal of the Chemical Society. Perkin transactions I, 1980, p. 1384 - 1389
  作者：Ames, Donald E.、Brohi, M. Ismail

  DOI：——

  日期：——