4-(cyclopenta-1,4-dien-1-yl)-6-ethyl-1,2-diethynyl-5-methylcyclohexa-1,3-diene | 1228307-04-7

• 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: 4-(cyclopenta-1,4-dien-1-yl)-6-ethyl-1,2-diethynyl-5-methylcyclohexa-1,3-diene
• CAS: 1228307-04-7
• 化学式: C₁₂H₁₀N₄OS
• 分子量: 258.304
• InChiKey: YRPYACLPMQLERV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.41
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(cyclopenta-1,4-dien-1-yl)-6-ethyl-1,2-diethynyl-5-methylcyclohexa-1,3-diene 在 bis(pyridine)iodonium (I) tetrafluoroborate 、 溴 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 6-(2,5-dibromothiophen-3-yl)-4-ethyl-3-oxo-3,4-dihydropyrazine-2-carbonitrile
  参考文献：
  名称：

  5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones 的合成、晶体结构和性质

  摘要：

  提出了一种合成 5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones 的简单方法。该方法基于相应的 2,3-二氰基吡嗪盐的水解。研究了吡嗪酮的光谱性质并对其进行了晶体学研究。显示了在微波活化条件下将 5-(het)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones 引入 [2+4] 环加成的可能性。

  DOI：

  10.1007/s11172-011-0142-7

文献信息

• Synthesis, X-ray crystal structure and antimycobacterial activity of enantiomerically pure 1-ethyl-2,3-dicyano-5-(het)aryl-6-hetaryl-1,6-dihydropyrazines
  作者：Egor V. Verbitskiy、Maria S. Toporova、Mikhail I. Kodess、Marina A. Ezhikova、Maksim L. Isenov、Marina G. Pervova、Marionella A. Kravchenko、Igor D. Medvinskiy、Sergey N. Skornyakov、Gennady L. Rusinov、Valery N. Charushin

  DOI：10.3998/ark.5550190.p008.690

  日期：——

  5-aryl-6-hetaryl substituted 1,6-dihydropyrazine derivatives. All dihydropyrazines were separated as pure enantiomers by chiral HPLC, and their absolute configurations for each pair of enantiomers have been determined by X-ray analysis. Individual enantiomers were screened in vitro for their antimycobacterial activities against Mycobacterium tuberculosis H37Rv, avium, terrae and extensively drug-resistant and

  1-烷基-2,3-二氰基-5-芳基吡嗪盐的 6-烷氧基加合物与芳族硼酸（如 2-噻吩基硼酸、2-呋喃基硼酸和 3-噻吩基硼酸）或其苯并类似物在二氯甲烷中的 Petasis 反应在室温下顺利形成相应的 5-芳基-6-杂芳基取代的 1,6-二氢吡嗪衍生物。所有二氢吡嗪均通过手性 HPLC 分离为纯对映异构体，并且通过 X 射线分析确定了每对对映异构体的绝对构型。在体外筛选了个体对映异构体对结核分枝杆菌 H37Rv、avium、terrae 和从乌拉尔地区（俄罗斯）结核病患者中分离的广泛耐药和多重耐药菌株的抗分枝杆菌活性。
• Synthesis, antimycobacterial and antifungal evaluation of some new 1-ethyl-5-(hetero)aryl-6-styryl-1,6-dihydropyrazine-2,3-dicarbonitriles
  作者：Egor V. Verbitskiy、Pavel A. Slepukhin、Marionella A. Kravchenko、Sergey N. Skornyakov、Natal’ya P. Evstigneeva、Nikolay V. Kungurov、Natal’ya V. Zil’berberg、Gennady L. Rusinov、Oleg N. Chupakhin、Valery N. Charushin

  DOI：10.1016/j.bmcl.2014.12.025

  日期：2015.2

  easy prepared in high yields from the corresponding pyrazinium salts by reduction with triethylsilane. All synthesized compounds were screened in vitro for their antifungal activities against seven pathogenic fungal strains and antimycobacterial activities against Mycobacterium tuberculosis H37Rv, avium, terrae and multi-drug-resistant strains isolated from tuberculosis patients in the Ural region (Russia)

  1-烷基-2,3-二氰基-5-芳基吡嗪鎓盐的6-羟基加合物与反式-苯乙烯基硼酸的Petasis反应在室温下顺利进行，得到了相应的5-（杂）芳基-6-苯乙烯基取代基1,6-二氢吡嗪衍生物。还发现C（6）未取代的1，6-二氢-或1,4,5,6-四氢吡嗪衍生物可以容易地由相应的吡嗪鎓盐通过用三乙基硅烷还原而以高收率制备。体外筛选了所有合成的化合物对七种病原真菌菌株的抗真菌活性以及对结核分枝杆菌H 37 Rv，鸟，土壤的抗分枝杆菌活性。 以及从乌拉尔地区（俄罗斯）的结核病患者中分离出的多药耐药菌株。
• A new approach to incorporate the carboranyl fragment into 2,5-diazabicyclo[2.2.2]oct-2-enes
  作者：Gennady L. Rusinov、Egor V. Verbitsky、Pavel A. Slepukhin、Olga N. Zabelina、Il’ya N. Ganebnykh、Valery N. Kalinin、Valentina A. Ol'shevskaya、Valery N. Charushin

  DOI：10.1016/j.mencom.2009.09.002

  日期：2009.9

  5-(Het)aryl-2,3-dicyano-1-ethylpyrazinium salts have been established to react with 9-allyl-ortho- and 9-allyl-meta-carboranes in the presence of sodium iodide into carboranylmethyl derivatives of 2,5-diazabicyclo[2.2.2]oct-2-ene.