[(1R,2R,6R,7S)-5-bromo-3,8-dioxa-4,9-diazatricyclo[5.2.1.02,6]dec-4-en-9-yl]-phenylmethanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1R,2R,6R,7S)-5-bromo-3,8-dioxa-4,9-diazatricyclo[5.2.1.02,6]dec-4-en-9-yl]-phenylmethanone
• 化学式: C₁₃H₁₁BrN₂O₃
• 分子量: 323.146
• InChiKey: KRZLQAINBPVBKM-YTWAJWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1R,2R,6R,7S)-5-bromo-3,8-dioxa-4,9-diazatricyclo[5.2.1.02,6]dec-4-en-9-yl]-phenylmethanone 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到
  参考文献：
  名称：

  Synthesis and molecular modeling of novel dihydroxycyclopentane-carbonitrile nor-nucleosides by bromonitrile oxide 1,3-dipolar cycloaddition

  摘要：

  The regioisomeric cycloadducts of the bromonitrile oxide to the N-benzoyl-2,3-oxazanorborn-5-ene were easily prepared and elaborated into a novel class of uracil nor-nucleoside derivatives. In the key-synthetic step represented by the reductive N-O bond cleavage, an unusual double ring opening afforded the aminol intermediates containing a beta-hydroxynitrile structure. By adapting known protocols, the aminols entered the linear construction of uracil rings. These novel nucleosides were found structurally similar to a potent antiviral compound, Brivudin, and molecular modeling and docking allowed to select one of the two regioisomeric structures as promising candidate for antiviral tests, due to the nice level of binding with the Thymidine Kinase, the enzyme involved in virus replication. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.086
• 作为产物：
  描述：

  1,1-二溴甲醛肟 、 N-benzoyl-2,3-oxazanorborn-5-ene 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 生成 8-benzoyl-5-bromo-3,9-dioxa-4,8-diazatricyclo[5.2.1.0(2,6)]dec-4-ene 、 [(1R,2R,6R,7S)-5-bromo-3,8-dioxa-4,9-diazatricyclo[5.2.1.02,6]dec-4-en-9-yl]-phenylmethanone
  参考文献：
  名称：

  Three-Dimensional Heterocycles: New Uracil-Based Structures Obtained by Nucleophilic Substitution at the sp2 Carbon of Bromoisoxazoline

  摘要：

  溴氰氧化物与N-苯甲酰-2,3-氧杂诺尔本-5-烯的区域异构环加成产物易于制备，并被进一步处理为一种新的以尿嘧啶为基础的支架。关键的合成步骤是在溴异噻唑啉三维杂环的sp2碳原子上进行亲核取代。亲核取代尿嘧啶负离子的合成方案经过优化，适应了底物的空间要求。我们以很好的收率制备了一系列的嘧啶衍生物，并对产物进行了全面表征。它们被提议作为核苷类似物，以及作为PNA结构中β-转角基序的合成子。

  DOI：

  10.3390/molecules19068661

文献信息

• Three-Dimensional Heterocycles: New Uracil-Based Structures Obtained by Nucleophilic Substitution at the sp2 Carbon of Bromoisoxazoline
  作者：Misal Memeo、Francesco Lapolla、Bruna Bovio、Paolo Quadrelli

  DOI：10.3390/molecules19068661

  日期：——

  The regioisomeric cycloadducts of bromonitrile oxide and N-benzoyl-2,3-oxaza-norborn-5-ene were easily prepared and elaborated into a novel class of uracil-based scaffolds. The key-synthetic step is the nucleophilic substitution at the sp2 carbon atom of the bromoisoxazoline three-dimensional heterocycles. The protocol to perform the nucleophilic substitution of uracil anions was optimized and adapted to the steric requirements of the substrates. A library of pyrimidine derivatives was prepared in very good yields and the products were fully characterized. They are proposed as nucleoside analogues and as synthons for β-turn motifs within PNA structures.

  溴氰氧化物与N-苯甲酰-2,3-氧杂诺尔本-5-烯的区域异构环加成产物易于制备，并被进一步处理为一种新的以尿嘧啶为基础的支架。关键的合成步骤是在溴异噻唑啉三维杂环的sp2碳原子上进行亲核取代。亲核取代尿嘧啶负离子的合成方案经过优化，适应了底物的空间要求。我们以很好的收率制备了一系列的嘧啶衍生物，并对产物进行了全面表征。它们被提议作为核苷类似物，以及作为PNA结构中β-转角基序的合成子。
• Synthesis and molecular modeling of novel dihydroxycyclopentane-carbonitrile nor-nucleosides by bromonitrile oxide 1,3-dipolar cycloaddition
  作者：Marco Savion、Misal Giuseppe Memeo、Bruna Bovio、Giovanni Grazioso、Laura Legnani、Paolo Quadrelli

  DOI：10.1016/j.tet.2011.12.086

  日期：2012.2

  The regioisomeric cycloadducts of the bromonitrile oxide to the N-benzoyl-2,3-oxazanorborn-5-ene were easily prepared and elaborated into a novel class of uracil nor-nucleoside derivatives. In the key-synthetic step represented by the reductive N-O bond cleavage, an unusual double ring opening afforded the aminol intermediates containing a beta-hydroxynitrile structure. By adapting known protocols, the aminols entered the linear construction of uracil rings. These novel nucleosides were found structurally similar to a potent antiviral compound, Brivudin, and molecular modeling and docking allowed to select one of the two regioisomeric structures as promising candidate for antiviral tests, due to the nice level of binding with the Thymidine Kinase, the enzyme involved in virus replication. (C) 2012 Elsevier Ltd. All rights reserved.