1-甲氧基-1-氮杂螺[5.5]十一碳-7,10-二烯-2,9-二酮 | 103831-03-4

• 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: 1-甲氧基-1-氮杂螺[5.5]十一碳-7,10-二烯-2,9-二酮
• 中文别名: 1-氮杂螺[5.5]十一碳-7,10-二烯-2,9-二酮,1-甲氧基-
• 英文名称: 1-methoxy-1-azaspiro[5.5]undeca-7,10-diene-2,9-dione
• CAS: 103831-03-4
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: SLOOLHBXXZYODV-UHFFFAOYSA-N

物化性质

• 熔点：
  112.6-112.7 °C
• 沸点：
  344.8±52.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(4-甲氧基苯基)丁基氯 在 次氯酸叔丁酯 、 sodium carbonate 、 silver carbonate 、 三氟乙酸 作用下， 以 乙醚 、 水 、 苯 为溶剂， 反应 35.33h， 生成 1-甲氧基-1-氮杂螺[5.5]十一碳-7,10-二烯-2,9-二酮
  参考文献：
  名称：

  Electrophilic aromatic substitution with N-methoxy-N-acylnitrenium ions generated from N-chloro-N-methoxy amides: syntheses of nitrogen heterocyclic compounds bearing a N-methoxy amide group

  摘要：

  DOI：

  10.1021/jo00275a027

文献信息

• N-alkoxy-n-acylnitrenium ions in intramolecular aromatic addition reactions
  作者：Stephen A. Glover、Andre Goosen、Cedric V. McClei、Johan L. Schoonraad

  DOI：10.1016/s0040-4020(01)81665-3

  日期：——

  solvents. These intermediates readily cyclise onto aromatic nuclei on alkozy side-chains to give benzoxazines and benzoxazepines and on the acyl side-chains to give γ, δ and ϵ benzolactams. Spirane products are formed by ipso addition When a 4-methoxy substituent ia present on the side-chain aromatic rings. The yields and regioselectivities of these reactions have been ascribed to different transition structures

  N-烷氧基-N-酰基硝鎓离子是通过在醚溶剂中用银离子处理N-烷氧基-N-氯酰胺类生成的。这些中间体很容易环化到醇酸侧链上的芳香核上，得到苯并恶嗪和苯并x氮平，以及酰基侧链上的γ，δ和ϵ苯并内酰胺。当在侧链芳环上存在4-甲氧基取代基时，通过ipso加成形成尖晶石产物。这些反应的产率和区域选择性归因于不同的过渡结构，用于环化到分别涉及胞外和环内N-0π键的酰基和烷氧基侧链上。从MNDO计算中获得了这种极高的π键特性的证据，该计算预测π键阶为0.9，旋转势垒为29.7 kcalmol -1
• First hypervalent iodine(<scp>iii</scp>)-catalyzed C–N bond forming reaction: catalytic spirocyclization of amides to N-fused spirolactams
  作者：Toshifumi Dohi、Akinobu Maruyama、Yutaka Minamitsuji、Naoko Takenaga、Yasuyuki Kita

  DOI：10.1039/b616510a

  日期：——

  A protic solvent, 2,2,2-trifluoroethanol (CF3CH2OH), was successfully introduced into hypervalent iodine(III)-involved catalytic cycles as an effective solvent, and the first iodoarene-catalyzed intramolecular carbon–nitrogen bond forming reaction was achieved under strong acid-free and mild conditions.

  在无强酸和温和的条件下，首次实现了碘烯烃催化的分子内碳氮键形成反应。
• Designer μ-oxo-bridged hypervalent iodine(iii) organocatalysts for greener oxidations
  作者：Toshifumi Dohi、Naoko Takenaga、Kei-ichiro Fukushima、Teruyoshi Uchiyama、Daishi Kato、Shiro Motoo、Hiromichi Fujioka、Yasuyuki Kita

  DOI：10.1039/c0cc03213a

  日期：——

  The in situ generated mu-oxo-bridged reactive hypervalent iodine(iii) species 1 or their analogues are introduced as more efficient organocatalysts for the catalytic strategy for realizing practical and greener oxidations.

  引入原位生成的mu-oxo桥连反应性高价碘（iii）物种1或它们的类似物，作为更有效的有机催化剂，用于实现实际和更绿色氧化的催化策略。
• Miyazawa, Etsuko; Sakamoto, Takeshi; Kikugawa, Yasuo, Heterocycles, 2003, vol. 59, # 1, p. 149 - 160
  作者：Miyazawa, Etsuko、Sakamoto, Takeshi、Kikugawa, Yasuo

  DOI：——

  日期：——
• Efficient Oxidative Spirolactamization by μ-Oxo Bridged Heterocyclic Hypervalent Iodine Compound
  作者：Yasuyuki Kita、Toshifumi Dohi、Eisuke Mochizuki、Daisuke Yamashita、Keitaro Miyazaki

  DOI：10.3987/com-13-s(s)11

  日期：——

  In this report, the authors have clarified that the mu-oxo bridged heterocyclic hypervalent iodine compound 1 shows a more effective reactivity in the oxidative dearomatizing spirolactamization compared to conventional PIDA (phenyliodine(III) diacetate). Besides the high reactivity, a new selectivity during the oxidations based on the steric discrimination of the nitrogen groups of the pre-spirocyclic substrates is demonstrated for the heterocyclic hypervalent iodine compound 1.