tert-butyl 7-allyl-9-oxo-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate | 1346688-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl 7-allyl-9-oxo-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate
• 英文别名: N-Boc-N'-allylbispidinone；Tert-butyl 9-oxo-7-prop-2-enyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate；tert-butyl 9-oxo-7-prop-2-enyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate
• CAS: 1346688-02-5
• 化学式: C₁₅H₂₄N₂O₃
• 分子量: 280.367
• InChiKey: BGZOEZIHHMYZAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  388.8±42.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 7-allyl-9-oxo-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate 在 1-氯乙基氯甲酸酯 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,1-二氯乙烷 、 乙腈 为溶剂， 反应 20.58h， 生成 Ethyl 2-[18-(2-ethoxy-2-oxoethylidene)-4,14-dioxo-3,6,12,15-tetrazapentacyclo[13.3.1.13,17.16,10.18,12]docosan-9-ylidene]acetate
  参考文献：
  名称：

  Modular Synthesis of Functionalized Bis-bispidine Tetraazamacrocycles

  摘要：

  An effective synthesis is reported for the construction of highly rigid and preorganized bis-bispidine tetraazamacrocycles bearing either identical or different functionalities. Using essential building blocks derived from N-Boc-N-allylbispidinone, the modular approach facilitates independent incorporation of the functional groups to the macrocyclic framework as well as selective derivatization of one functionality in the presence of another.

  DOI：

  10.1021/ol202840s
• 作为产物：
  描述：

  聚合甲醛 、 N-叔丁氧羰基-4-哌啶酮 、 丙烯胺 在 盐酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 16.5h， 生成 tert-butyl 7-allyl-9-oxo-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate
  参考文献：
  名称：

  [EN] NOVEL ANTIBIOTICS AND METHODS OF USING SAME
  [FR] NOUVEAUX ANTIBIOTIQUES ET MÉTHODES D'UTILISATION DE CEUX-CI

  摘要：

  本发明涵盖了新型的3,6-二氮杂双环[3.1.1]庚烷抗生素化合物及其任何盐或溶剂化合物。本发明还涵盖了制备这种化合物的方法，以及利用这种化合物治疗受试者细菌感染的方法。

  公开号：

  WO2018075871A1

文献信息

• Effective synthesis of bis-bispidinone and facile difunctionalization of highly rigid macrocyclic tetramines
  作者：Md. Jahirul Islam、Erin J. Miller、Jacob S. Gordner、Deep Patel、Zhuo Wang

  DOI：10.1016/j.tetlet.2013.02.028

  日期：2013.4

  An effective synthesis which provides facile access to highly rigid tetraazamacrocycles possessing labile functional groups is reported. Essential to the approach is bis-bispidinone, a versatile substrate which can be prepared from an unusually stable bispidine diethyl ketal building block and requires a non-aqueous isolation process. Further functionalization of the substrate allows direct and concurrent incorporation of functionalities onto the bis-bispidine tetraazamacrocyclic framework, in particular those that are labile during the macrocycle formation. (C) 2013 Elsevier Ltd. All rights reserved.
• [EN] NOVEL ANTIBIOTICS AND METHODS OF USING SAME<br/>[FR] NOUVEAUX ANTIBIOTIQUES ET MÉTHODES D'UTILISATION DE CEUX-CI
  申请人：BROAD INST INC

  公开号：WO2018075871A1

  公开（公告）日：2018-04-26

  The present invention includes novel 3,6-diazabicyclo[3.1.1]heptane antibiotic compounds and any salts or solvates thereof. The present invention further includes methods of preparing such compounds, and methods of treating bacterial infection in a subject using such compounds.

  本发明涵盖了新型的3,6-二氮杂双环[3.1.1]庚烷抗生素化合物及其任何盐或溶剂化合物。本发明还涵盖了制备这种化合物的方法，以及利用这种化合物治疗受试者细菌感染的方法。
• Modular Synthesis of Functionalized Bis-bispidine Tetraazamacrocycles
  作者：Zhuo Wang、Erin J. Miller、Samantha J. Scalia

  DOI：10.1021/ol202840s

  日期：2011.12.16

  An effective synthesis is reported for the construction of highly rigid and preorganized bis-bispidine tetraazamacrocycles bearing either identical or different functionalities. Using essential building blocks derived from N-Boc-N-allylbispidinone, the modular approach facilitates independent incorporation of the functional groups to the macrocyclic framework as well as selective derivatization of one functionality in the presence of another.