6-phenylfuro[2,3-b]pyrazine | 66479-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-phenylfuro[2,3-b]pyrazine
• CAS: 66479-90-1
• 化学式: C₁₂H₈N₂O
• 分子量: 196.208
• InChiKey: FSEDFAYOEWWTBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-phenylfuro[2,3-b]pyrazine 生成 3-Chlor-2-phenylfuro <2,3-b> pyrazin
  参考文献：
  名称：

  Kruse,C.G. et al., Recueil des Travaux Chimiques des Pays-Bas, 1978, vol. 97, p. 151 - 155

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2-oxo-2-phenyl-ethyl)-1H-pyrazin-2-one 在 硫酸 作用下， 反应 5.0h， 生成 6-phenylfuro[2,3-b]pyrazine
  参考文献：
  名称：

  Timmermans,P.B.M.W.M. et al., Recueil des Travaux Chimiques des Pays-Bas, 1978, vol. 97, # 3, p. 81 - 84

  摘要：

  DOI：

文献信息

• Transition metal free hydrolysis/cyclization strategy in a single pot: synthesis of fused furo N-heterocycles of pharmacological interest
  作者：Ali Nakhi、Md. Shafiqur Rahman、Guru Pavan Kumar Seerapu、Rakesh Kumar Banote、Kummari Lalith Kumar、Pushkar Kulkarni、Devyani Haldar、Manojit Pal

  DOI：10.1039/c3ob41069b

  日期：——

  A transition metal free tandem two-step strategy has been developed involving hydrolysis of 2-chloro-3-alkynyl quinoxalines/pyrazines followed by in situ cyclization of the corresponding 2-hydroxy-3-alkynyl intermediates in a single pot leading to fused furo N-heterocycles as potential inhibitors of sirtuins. A representative compound showed promising pharmacological properties in vitro and in vivo.

  开发了一种无过渡金属的分段两步策略，该策略涉及2-氯-3-炔基喹喔啉/吡嗪的裂解，随后在单一反应容器中现场环化相应的2-羟基-3-炔基中间体，得到可能作为去乙酰化酶抑制剂的融合呋喃N-杂环化合物。其中一个代表性化合物在体外和体内均显示出有希望的药理学特性。
• Trifluoroacetic Acid Mediated One-Pot Synthesis of Furo-Fused Quinoxalines/Pyrazines
  作者：Kapil Mohan Saini、Sonu Kumar、Monika Patel、Rakesh K. Saunthwal、Akhilesh K. Verma

  DOI：10.1002/ejoc.201700541

  日期：2017.7.7

  A trifluoroacetic acid promoted step-economical one-pot approach to the synthesis of furo-fused quinoxalines/pyrazines by the reaction of 2,3-dichloroquinoxalines/pyrazines with alkynes is described. The reaction involves a selective in-situ Sonogashira coupling step and a hydroxylation followed by a metal-free 5-endo-dig cyclization. Preliminary experiments show that trifluoroacetic acid acts as a

  描述了通过2,3-二氯喹喔啉/吡嗪与炔烃反应合成呋喃稠合的喹喔啉/吡嗪的三氟乙酸促进的一步经济型一锅法。该反应包括选择性的原位Sonogashira偶联步骤和羟基化，然后是无金属的5 -endo-dig环化。初步实验表明，三氟乙酸是氧合步骤中的氧气来源，同位素标记研究支持了这种机制，即机理涉及酸性介质对炔烃的活化作用。可以耐受各种取代基，这对结构和生物学研究应具有重要意义。
• Highly selective substitutions in 2,3-dichloropyrazine. A novel general approach to aloisines
  作者：Dmitriy S. Chekmarev、Sergey V. Shorshnev、Alexander E. Stepanov、Alexander N. Kasatkin

  DOI：10.1016/j.tet.2006.08.018

  日期：2006.10

  A highly efficient synthesis of the potent CDKs (cyclin-dependent kinases) inhibitors, aloisines (substituted 5H-pyrrolo[2,3b]pyrazines) is presented. The method is based on highly selective monosubstitution of a single chlorine atom in 2,3-dichloropyrazine with lithiated ketones, esters, and nitriles followed by co-cyclization of the resulting intermediates with primary amines or hydrazines. (c) 2006 Elsevier Ltd. All rights reserved.
• Electrochemical and chemical reduction of furopyrazines, thienopyrazines, furoquinoxalines and thienoquinoxalines
  作者：Joseph Armand、Christian Bellec、Line Boulares、Patrick Chaquin、Daniel Masure、Jean Pinson

  DOI：10.1021/jo00016a008

  日期：1991.8

  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.
• TIMMERMANS P. B. M. W. M.; KRUSE C. G..; GEN A. VAN DER, REC. TRAV. CHIM., 1978, 97, NO 3, 81-84
  作者：TIMMERMANS P. B. M. W. M.、 KRUSE C. G..、 GEN A. VAN DER

  DOI：——

  日期：——