N-BOC-三恶烷 | 1020002-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 中文名称: N-BOC-三恶烷
• 英文名称: N-boc-trioxane
• CAS: 1020002-82-7
• 化学式: C₂₁H₃₃NO₅
• 分子量: 379.497
• InChiKey: ZJPGSVSZIQWDTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-BOC-三恶烷 在 盐酸 作用下， 以 乙醚 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  Two-Step Synthesis of Achiral Dispiro-1,2,4,5-tetraoxanes with Outstanding Antimalarial Activity, Low Toxicity, and High-Stability Profiles

  摘要：

  A rapid, two-step synthesis of a range of dispiro-1,2.4,5-tetraoxanes with potent antimalarial activity both in vitro and in vivo has been achieved. These 1,2,4,5-tetraoxanes have been proven to be superior to 1,2,4-trioxolanes in terms of stability and to be superior to trioxane analogues in terms of both stability and activity. Selected analogues have in vitro nanomolar antimalarial activity and good oral activity and are nontoxic in screens for both cytotoxicity and genotoxicity. The synthesis of a fluorescent 7-nitrobenza-2-oxa-1,3-diazole (NBD) tagged tetraoxane probe and use of laser scanning confocal microscopy techniques have shown that tagged molecules accumulate selectively only in parasite infected erythrocytes and that intraparasitic formation of adducts could be inhibited by co-incubation with the iron chelator desferrioxamine (DFO).

  DOI：

  10.1021/jm701435h
• 作为产物：
  描述：

  1-噁-6-氮杂螺[2.5]辛烷-6-羧酸-1,1-二甲基乙酯 在 双氧水 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-BOC-三恶烷
  参考文献：
  名称：

  二氧化硅硫酸催化合成非对称二螺-1,2,4,5-四恶烷和二螺-1,2,4-三恶烷

  摘要：

  报道了一种由非均相二氧化硅硫酸 (SSA) 催化剂促进的非对称 1,2,4,5-四恶烷和 1,2,4-三恶烷的制备新方案。不同酮类温和条件下反应，与宝石-dihydroperoxides或peroxysilyl醇/β-氢过氧醇以产生良好的产率相应的内过氧化物。我们的机械建议，在分子轨道计算的帮助下，在 ωB97XD/def2-TZVPP/PCM(DCM)//B3LYP/6-31G(d) 理论水平，增强了 SSA 在环缩聚步骤中的作用。这种新方法与以前报道的方法不同，它使用易于获得且价格低廉的试剂，具有可回收的特性，从而为合成新的生物活性内过氧化物建立了一种有效的替代方法。

  DOI：

  10.1021/acs.joc.1c01258

文献信息

• Piperidine dispiro-1,2,4-trioxane analogues
  作者：Sunil Sabbani、Paul A. Stocks、Gemma L. Ellis、Jill Davies、Erik Hedenstrom、Stephen A. Ward、Paul M. O’Neill

  DOI：10.1016/j.bmcl.2008.09.052

  日期：2008.11

  Dispiro N-Boc-protected 1,2,4-trioxane 2 was synthesised via Mo(acac)(2) catalysed perhydrolysis of N-Boc spirooxirane followed by condensation of the resulting beta-hydroperoxy alcohol 10 with 2-adamantanone. N-Boc 1,2,4-trioxane 2 was converted to the amine 1,2,4-trioxane hydrochloride salt 3 which was subsequently used to prepare derivatives (4-7). Several of these novel 1,2,4-trioxanes had nanomolar antimalarial activity versus the 3D7 strain of Plasmodium falciparum. Amine intermediate 3 represents a versatile derivative for the preparation of achiral arrays of trioxane analogues with antimalarial activity. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Non-symmetrical Dispiro-1,2,4,5-Tetraoxanes and Dispiro-1,2,4-Trioxanes Catalyzed by Silica Sulfuric Acid
  作者：Patrícia S. M. Amado、Luís M. T. Frija、Jaime A. S. Coelho、Paul M. O’Neill、Maria L. S. Cristiano

  DOI：10.1021/acs.joc.1c01258

  日期：2021.8.6

  A novel protocol for the preparation of non-symmetrical 1,2,4,5-tetraoxanes and 1,2,4-trioxanes, promoted by the heterogeneous silica sulfuric acid (SSA) catalyst, is reported. Different ketones react under mild conditions with gem-dihydroperoxides or peroxysilyl alcohols/β-hydroperoxy alcohols to generate the corresponding endoperoxides in good yields. Our mechanistic proposal, assisted by molecular

  报道了一种由非均相二氧化硅硫酸 (SSA) 催化剂促进的非对称 1,2,4,5-四恶烷和 1,2,4-三恶烷的制备新方案。不同酮类温和条件下反应，与宝石-dihydroperoxides或peroxysilyl醇/β-氢过氧醇以产生良好的产率相应的内过氧化物。我们的机械建议，在分子轨道计算的帮助下，在 ωB97XD/def2-TZVPP/PCM(DCM)//B3LYP/6-31G(d) 理论水平，增强了 SSA 在环缩聚步骤中的作用。这种新方法与以前报道的方法不同，它使用易于获得且价格低廉的试剂，具有可回收的特性，从而为合成新的生物活性内过氧化物建立了一种有效的替代方法。
• Two-Step Synthesis of Achiral Dispiro-1,2,4,5-tetraoxanes with Outstanding Antimalarial Activity, Low Toxicity, and High-Stability Profiles
  作者：Gemma L. Ellis、Richard Amewu、Sunil Sabbani、Paul A. Stocks、Alison Shone、Deborah Stanford、Peter Gibbons、Jill Davies、Livia Vivas、Sarah Charnaud、Emily Bongard、Charlotte Hall、Karen Rimmer、Sonia Lozanom、María Jesús、Domingo Gargallo、Stephen A. Ward、Paul M. O’Neill

  DOI：10.1021/jm701435h

  日期：2008.4.1

  A rapid, two-step synthesis of a range of dispiro-1,2.4,5-tetraoxanes with potent antimalarial activity both in vitro and in vivo has been achieved. These 1,2,4,5-tetraoxanes have been proven to be superior to 1,2,4-trioxolanes in terms of stability and to be superior to trioxane analogues in terms of both stability and activity. Selected analogues have in vitro nanomolar antimalarial activity and good oral activity and are nontoxic in screens for both cytotoxicity and genotoxicity. The synthesis of a fluorescent 7-nitrobenza-2-oxa-1,3-diazole (NBD) tagged tetraoxane probe and use of laser scanning confocal microscopy techniques have shown that tagged molecules accumulate selectively only in parasite infected erythrocytes and that intraparasitic formation of adducts could be inhibited by co-incubation with the iron chelator desferrioxamine (DFO).