2,6-dichloro-3-phenylpyrazine | 64163-11-7

• 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: 2,6-dichloro-3-phenylpyrazine
• 英文别名: 2,6-dichloro-5-phenylpyrazine；3,5-dichloro-2-phenylpyrazine；3,5-dichloro-2-phenyl-pyrazine；2,6-Dichlor-5-phenylpyrazin；Pyrazine, 3,5-dichloro-2-phenyl-
• CAS: 64163-11-7
• 化学式: C₁₀H₆Cl₂N₂
• 分子量: 225.077
• InChiKey: OWUVLMAZWWVMKK-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  122-123 °C(Press: 0.1 Torr)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 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

反应信息

• 作为反应物：
  描述：

  2,6-dichloro-3-phenylpyrazine 在 马来酸酐 、 双氧水 作用下， 以 氯仿 为溶剂， 以65%的产率得到3,5-dichloro-2-phenylpyrazine 1-oxide
  参考文献：
  名称：

  Ohta, Akihiro; Watanabe, Tokuhiro; Akita, Yasuo, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1061 - 1067

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯基吡嗪 在 马来酸酐 、 双氧水 、 三氯氧磷 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 6.5h， 生成 2,6-dichloro-3-phenylpyrazine
  参考文献：
  名称：

  Ohta, Akihiro; Watanabe, Tokuhiro; Akita, Yasuo, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1061 - 1067

  摘要：

  DOI：

文献信息

• Studies on pyrazines. 35. An improved synthesis of bromopyrazines from hydroxypyrazines
  作者：Nobuhiro Sato、Nobuhiko Narita

  DOI：10.1002/jhet.5570360334

  日期：1999.5

  The synthesis of bromopyrazines from hydroxypyrazines was successfully effected by the procedure via trimethylsilyloxypyrazines, the sequence of which proceeds under mild conditions and does not require the isolation of intermediate.

  通过三甲基甲硅烷基氧基吡嗪的方法成功地从羟基吡嗪合成了溴吡嗪，其顺序在温和的条件下进行并且不需要分离中间体。
• Arylation, Vinylation, and Alkynylation of Electron-Deficient (Hetero)arenes Using Iodonium Salts
  作者：Chuan Liu、Qiu Wang

  DOI：10.1021/acs.orglett.6b02550

  日期：2016.10.7

  Arylation, vinylation, and alkynylation of electron-deficient arenes and heteroarenes have been achieved by chemoselective C–H zincation followed by copper-catalyzed coupling reactions using iodonium salts. This approach offers a direct and general access to a wide scope of (hetero)biaryls as well as alkenylated and alkynylated heteroarenes under mild conditions. It is particularly useful and valuable

  电子不足的芳烃和杂芳烃的芳构化，乙烯基化和炔基化反应是通过化学选择性的C–H锌化反应，然后使用碘鎓盐在铜催化下进行偶联反应而实现的。这种方法可在温和条件下直接和通用地获得各种（杂）联芳基以及烯基化和炔基化的杂芳烃。如瞬态受体电位类香草素1（TRPV1）拮抗剂和血管紧张素II受体1型（AT1受体）拮抗剂的合成所证明的，它对于多种（杂）芳基化合物的快速模块化合成特别有用且有价值。
• Sato, Nobuhiro, Journal of Chemical Research, Miniprint, 1984, # 10, p. 2860 - 2875
  作者：Sato, Nobuhiro

  DOI：——

  日期：——
• Discovery of First-in-Class, Potent, and Orally Bioavailable Embryonic Ectoderm Development (EED) Inhibitor with Robust Anticancer Efficacy
  作者：Ying Huang、Jeff Zhang、Zhengtian Yu、Hailong Zhang、Youzhen Wang、Andreas Lingel、Wei Qi、Justin Gu、Kehao Zhao、Michael D. Shultz、Long Wang、Xingnian Fu、Yongfeng Sun、Qiong Zhang、Xiangqing Jiang、Jiangwei Zhang、Chunye Zhang、Ling Li、Jue Zeng、Lijian Feng、Chao Zhang、Yueqin Liu、Man Zhang、Lijun Zhang、Mengxi Zhao、Zhenting Gao、Xianghui Liu、Douglas Fang、Haibing Guo、Yuan Mi、Tobias Gabriel、Michael P. Dillon、Peter Atadja、Counde Oyang

  DOI：10.1021/acs.jmedchem.6b01576

  日期：2017.3.23

  Overexpression and somatic heterozygous mutations of EZH2, the catalytic subunit of polycomb repressive complex 2 (PRC2), are associated with several tumor types. EZH2 inhibitor, EPZ-6438 (tazemetostat), demonstrated clinical efficacy in patients with acceptable safety profile as monotherapy. EED, another subunit of PRC2 complex, is essential for its histone methyltransferase activity through direct binding to trimethylated lysine 27 on histone 3 (H3K27Me3). Herein we disclose the discovery of a first-in-class potent, selective, and orally bioavailable EED inhibitor compound 43 (EED226). Guided by X-ray crystallography, compound 43 was discovered by fragmentation and regrowth of compound 7, a PRC2 HTS hit that directly binds EED. The ensuing scaffold hopping followed by multiparameter optimization led to the discovery of 43. Compound 43 induces robust and sustained tumor regression in EZH2(MUT) preclinical DLBCL model. For the first time we demonstrate that specific and direct inhibition of EED can be effective as an anticancer strategy.
• Sato, Nobuhiro, Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 149 - 152
  作者：Sato, Nobuhiro

  DOI：——

  日期：——