tert-butyl 3-(((3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl)methyl)-1H-indole-1-carboxylate | 310462-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl 3-(((3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl)methyl)-1H-indole-1-carboxylate
• 英文别名: tert-butyl 3-[[(3S,8aS)-1,4-dioxo-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-3-yl]methyl]indole-1-carboxylate
• CAS: 310462-38-5
• 化学式: C₂₁H₂₅N₃O₄
• 分子量: 383.447
• InChiKey: YMBWWWKPLURITN-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(((3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl)methyl)-1H-indole-1-carboxylate 在 mercury(II) trifluoroacetate 、 碘 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到cyclo-(1-tert-butoxycarbonyl-2-iodo-L-tryptophanyl)-L-prolinyl
  参考文献：
  名称：

  Copper-Catalyzed Cyclization of Iodo-tryptophans: A Straightforward Synthesis of Pyrroloindoles

  摘要：

  Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, affording a wide range of polysubstituted, enantioenriched tetrahydropyrrolo[2,3-b]indoles. Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems.

  DOI：

  10.1021/ol8015513
• 作为产物：
  描述：

  (3S,8aS)-3-(1H-吲哚-3-基甲基)-2,3,6,7,8,8a-六氢吡咯并[2,1-f]吡嗪-1,4-二酮 在 4-二甲氨基吡啶 、 二甲胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 tert-butyl 3-(((3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl)methyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of microtubule assembly inhibition and cytotoxicity of prenylated derivatives of cyclo-l-Trp-l-Pro

  摘要：

  The synthesis of three isoprenylated derivatives of cyclo-L-Trp-L-Pro is described. These substances have been evaluated for cytotoxic activity in rat normal fibroblast 3Y1 cells and have also been evaluated in vitro for the inhibition of microtubule assembly. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00171-1

文献信息

• Studies towards the Total Synthesis of Drimentine C. Preparation of the AB and CDEF Ring Fragments
  作者：Sarah M. Pound、Steven J. Underwood、Christopher J. Douglas

  DOI：10.1002/ejoc.202000158

  日期：2020.5.3

  Herein we report our efforts toward the total synthesis of drimentine C using three distinct approaches incorporating palladium-catalyzed cyanoamidation, reductive cross-coupling, and photoredox-catalyzed α-alkylation of an aldehyde as key steps. Our synthetic efforts use a convergent synthesis to assemble the terpenoid and alkaloid portions of drimentine C from readily available l-tryptophan, l-proline

  drimentine 家族是一类源自放线菌的杂合类异戊二烯。该家族的成员显示出较弱的抗肿瘤和抗菌活性。在此，我们报告了我们使用三种不同的方法全合成 drimentine C 的努力，这些方法包括钯催化的氰基酰胺化、还原交叉偶联和光氧化还原催化的醛的 α-烷基化作为关键步骤。我们的合成工作使用收敛合成法从现成的 l-色氨酸、l-脯氨酸和 (+)-sclareolide 中组装 drimentine C 的萜类和生物碱部分。
• Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification
  作者：Bahaa El-Dien M. El-Gendy、Mostafa E. Rateb

  DOI：10.1016/j.bmcl.2015.06.010

  日期：2015.8

  Nine diketopiperazines were characterized from the culture of marine fungal isolate MR2012 which based on DNA amplification and sequencing of the fungal internal transcribed spacer (ITS) region was identified as Aspergillus fumigatus. The isolated fungal metabolites 4-12 were unambiguously identified as a series of simple and re-arranged diketopiperazines by analysis of spectroscopic data. t-Butoxycarbonyl group (BOC) derivatization was used to separate the intractable mixture of 4 and 5. When all compounds were evaluated for antimicrobial activity against gram positive bacteria, the isolated metabolites showed moderate to weak effects, while the semisynthetic derivatives 4a and 5a displayed strong activity comparable to the positive control, tetracycline against gram positive bacteria. (C) 2015 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Cyclization of Iodo-tryptophans: A Straightforward Synthesis of Pyrroloindoles
  作者：Alexis Coste、Mathieu Toumi、Karen Wright、Vanessa Razafimahaléo、François Couty、Jérome Marrot、Gwilherm Evano

  DOI：10.1021/ol8015513

  日期：2008.9.1

  Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, affording a wide range of polysubstituted, enantioenriched tetrahydropyrrolo[2,3-b]indoles. Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems.
• Synthesis and evaluation of microtubule assembly inhibition and cytotoxicity of prenylated derivatives of cyclo-l-Trp-l-Pro
  作者：Juan F Sanz-Cervera、Emily M Stocking、Takeo Usui、Hiroyuki Osada、Robert M Williams

  DOI：10.1016/s0968-0896(00)00171-1

  日期：2000.10

  The synthesis of three isoprenylated derivatives of cyclo-L-Trp-L-Pro is described. These substances have been evaluated for cytotoxic activity in rat normal fibroblast 3Y1 cells and have also been evaluated in vitro for the inhibition of microtubule assembly. (C) 2000 Elsevier Science Ltd. All rights reserved.