(S)-(4,5-dibromo-1H-pyrrol-2-yl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone | 446878-43-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-(4,5-dibromo-1H-pyrrol-2-yl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone
• 英文别名: (4,5-dibromo-1H-pyrrol-2-yl)-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methanone
• CAS: 446878-43-9
• 化学式: C₁₀H₁₂Br₂N₂O₂
• 分子量: 352.025
• InChiKey: AKKOIWYXWGPSRY-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(4,5-dibromo-1H-pyrrol-2-yl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone 在 三氯氧磷 、 2-碘酰基苯甲酸 作用下， 以 吡啶 、 二甲基亚砜 为溶剂， 反应 18.0h， 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：

  Synthesis of the dipyrrolopyrazinone core of dibromophakellstatin and related marine alkaloids

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)00600-7
• 作为产物：
  描述：

  4,5-二溴-1H-吡咯-2-羧酸 在 4-二甲氨基吡啶 、 锂硼氢 、 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 18.0h， 生成 (S)-(4,5-dibromo-1H-pyrrol-2-yl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone
  参考文献：
  名称：

  Total Synthesis of the Natural Product (±)-Dibromophakellin and Analogues

  摘要：

  (+/-)-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。

  DOI：

  10.1021/ol201741r

文献信息

• Study on the absolute configuration of (−)-palau’amine
  作者：Thomas Lindel、Delphine E.N. Jacquot、Michael Zöllinger、Robin B. Kinnel、Shayna McHugh、Matthias Köck

  DOI：10.1016/j.tetlet.2010.09.148

  日期：2010.12

  absolute stereochemistry of the immunosuppressive pyrrole–imidazole alkaloid (−)-palau’amine from the marine sponge Stylotella aurantium is analyzed by CD spectroscopy. With the help of a series of model compounds it is shown that the CD spectrum of (−)-palau’amine can be explained based on the assumption that the pyrrolopyrazinone partial structure is planar in 2,2,2-trifluoroethanol (TFE). Surprisingly

  通过CD光谱法分析了来自海洋海绵金丝桃的免疫抑制性吡咯-咪唑生物碱（-）- palau'amine的绝对立体化学。借助于一系列模型化合物，表明可以基于在2,2,2-三氟乙醇（TFE）中吡咯并吡嗪酮的部分结构是平面的假设来解释（-）-palau'amine的CD光谱。出乎意料的是，尽管表现出相同的绝对构型，天然产物（-）-二溴邻苯并菲林显示出相反的棉花效应。
• 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。
• 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.