7,8-dibromo-2,3-dihydro-1H-dipyrrolo[1,2-a;1',2'-d]pyrazine-5-one | 446878-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡嗪类
• 英文名称: 7,8-dibromo-2,3-dihydro-1H-dipyrrolo[1,2-a;1',2'-d]pyrazine-5-one
• 英文别名: 7,8-dibromo-2,3-dihydro-1H-dipyrrolo[1,2-a;1',2'-d]pyrazin-5-one；7,8-dibromo-2,3-dihydrodipyrrolo[1,2-a:1',2'-d]pyrazin-5(1H)-one；5,6-Dibromo-1,7-diazatricyclo[7.3.0.03,7]dodeca-3,5,8-trien-2-one
• CAS: 446878-34-8
• 化学式: C₁₀H₈Br₂N₂O
• 分子量: 331.994
• InChiKey: QIWWYCSZCMPEEM-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C(Solv: methanol (67-56-1))
• 沸点：
  339.5±42.0 °C(Predicted)
• 密度：
  2.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7,8-dibromo-2,3-dihydro-1H-dipyrrolo[1,2-a;1',2'-d]pyrazine-5-one 在 samarium diiodide 、 calcium oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.17h， 生成 rac-N-ethoxycarbonyl-dibromophakellstatin
  参考文献：
  名称：

  通过三组分咪唑烷酮二元醇盐合成全细胞生长的海洋天然产物Dibromophakellstatin。

  摘要：

  来自海洋海绵Phakellia mauritiana的四环吡咯-咪唑生物碱二溴环已抑菌素已从吡咯经七个步骤合成，总收率为18％。关键步骤是三环烯酰胺，腈和氨基甲酰基结构单元的三组分组装，一步即可得到二溴环己汀的咪唑烷酮环。值得注意的是，可以将具有双重功能的试剂EtO 2 CNHOTs用作亲电子腈和偶极氨基甲酰基组分的来源。使用脱溴的前体双吡咯并吡嗪酮可以提高高得率，并允许我们开发第二代合成方法。确认了二溴泛函他汀的细胞抑制活性。

  DOI：

  10.1021/jo061813u
• 作为产物：
  描述：

  L-脯氨酸甲酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 甲烷磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.7h， 生成 7,8-dibromo-2,3-dihydro-1H-dipyrrolo[1,2-a;1',2'-d]pyrazine-5-one
  参考文献：
  名称：

  Regioselective intramolecular N1–C3 cyclizations on pyrrole–proline to ABC tricycles of dibromophakellin and ugibohlin

  摘要：

  Pyrrole N1-C and C3-C regioselective linkage to the fused tricycle ABC system present in the marine metabolites ugibohlin and dibromoisophakellin is described. The cyclization is closely dependent oil the electrophilic function. bromination degree of the pyrrole moiety and pH conditions. The mechanism of the functionalization of the ABC olefin by oxidative agents was found to occur through an N-acyliminium intermediate as showed by the natural chemical connection between ugibohlin and dibromoisophakellin. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.11.066

文献信息

• Total Synthesis of the Natural Product (±)-Dibromophakellin and Analogues
  作者：Nicole M. Hewlett、Jetze J. Tepe

  DOI：10.1021/ol201741r

  日期：2011.9.2

  (+/-)-Dibromophakellin has been synthesized in two steps from a known alkene intermediate. The key step in the synthesis is the NBS olefin activation to facilitate the addition of a guanidine molecule across the double bond.

  (+/-)-二溴化法凯林通过两步反应从已知的烯烃中间体合成。合成的关键步骤是使用NBS（N-溴代琥珀酰亚胺）活化烯烃，从而促进胍分子在双键上的加成。
• Skeleton Diversity by Cyclopropanation of Tricyclic Acylenamines
  作者：Michael Zöllinger、Peter Mayer、Thomas Lindel

  DOI：10.1515/znb-2009-0605

  日期：2009.6.1

  Aiming at the structural diversification of phakellin- and isophakellin-type pyrrole-imidazole alkaloids on the skeleton level, the reaction of dipyrrolopyrazinones and pyrroloindolizines with dichlorocarbene was investigated. Conversions resulted in ring expansion affording novel chlorinated and brominated dipyrroloazepinones, pyridopyrroloazepinones, and dipyrrolopyrazinones. Structures of the tetracyclic products with hitherto unknown architectures have been secured by X-ray analyses.

  针对phakellin和isophakellin型吡咯-咪唑生物碱骨架层面的结构多样性，研究了二吡咯吡嗪酮和吡咯吲哚嗪与二氯卡宾的反应。转化产生了环扩张，得到了新的氯化和溴化二吡咯氮杂环酮、吡啶二吡咯氮杂环酮和二吡咯吡嗪酮。通过X射线分析，确定了具有迄今未知结构的四环产物的结构。
• Amidative Cyclization of Alkynyl Esters to Access Pyrazin-1(2<i>H</i>)-ones: Application to the Synthesis of Peramine and Dibromophakellin
  作者：Laxmikant D. Gangnale、Satya Ravi Teja Miriyala、Kalyan Kumar Pasunooti、D. Srinivasa Reddy

  DOI：10.1021/acs.joc.3c02157

  日期：2023.12.15

  Herein, we report an efficient 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-catalyzed tandem intermolecular amidation and regioselective intramolecular 6-exo-dig cyclization of alkynyl esters to efficiently access pyrazine-1(2H)-one scaffolds. This organo-catalyzed [5 + 1] annulation features a broad substrate scope concerning both annulating partners. Total syntheses of peramine and formal syntheses

  在此，我们报道了一种有效的1,5,7-三氮杂双环[4.4.0]dec-5-ene（TBD）催化的串联分子间酰胺化和炔基酯的区域选择性分子内6- exo -dig环化，以有效地获得pyrazine-1( 2 H )-一个支架。这种有机催化的 [5 + 1] 成环具有涉及两个成环伴侣的广泛底物范围。实现了波胺的全合成和二溴邻苯二甲酸酯天然产物的形式合成，展示了该方法的应用潜力。
• Synthesis of the dipyrrolopyrazinone core of dibromophakellstatin and related marine alkaloids
  作者：Delphine E.N. Jacquot、Holger Hoffmann、Kurt Polborn、Thomas Lindel

  DOI：10.1016/s0040-4039(02)00600-7

  日期：2002.5

  The dipyrrolopyrazinone (ABC) core of the phakelline-type pyrrole-imidazole alkaloids from marine sponges was synthesized starting from L-prolinol and 2-trichloroacetylated pyrroles. On oxidation of the condensation product with IBX, immediate cyclization occurs. It was found that the presence of a bromine substituent in the 8-position of the resulting tricyclic N,O-hemiacetal exclusively favors the cis relative configuration at the stereogenic centers C10 and C10a. Via an intermediate tertiary N-acyliminium ion, the pyrazinone core was dihydroxylated by treatment with m-CPBA in the presence of water. The simultaneous functionalization of the C10 and C10a positions is an important step towards the synthesis of the cytotoxic natural product dibromophakellstatin (C) 2002 Elsevier Science Ltd. All rights reserved.
• Total Synthesis of the Marine Natural Product<i>rac</i>-Dibromophakellstatin
  作者：Delphine E. N. Jacquot、Michael Zöllinger、Thomas Lindel

  DOI：10.1002/anie.200462252

  日期：2005.4.8