tert-butyl 9-methylene-3-oxo-2-oxa-7-azaspiro[4.4]nonane-7-carboxylate | 1428154-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl 9-methylene-3-oxo-2-oxa-7-azaspiro[4.4]nonane-7-carboxylate
• 英文别名: Tert-butyl 9-methylidene-3-oxo-2-oxa-7-azaspiro[4.4]nonane-7-carboxylate；tert-butyl 9-methylidene-3-oxo-2-oxa-7-azaspiro[4.4]nonane-7-carboxylate
• CAS: 1428154-12-4
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: BUXOZTCOITZAME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl (5-oxo-2,5-dihydrofuran-3-yl)methyl(prop-2-ynyl)carbamate 以 乙醚 为溶剂， 反应 1.0h， 以59%的产率得到tert-butyl 9-methylene-3-oxo-2-oxa-7-azaspiro[4.4]nonane-7-carboxylate
  参考文献：
  名称：

  Conformationally restricted pyrrolidines by intramolecular [2+2] photocycloaddition reactions

  摘要：

  多种取代的N-Boc保护的4-(烯丙胺甲基)-2(5H)-呋喃酮的分子内[2+2]光环加成反应，产生具有三个空间上定义的位置供进一步功能化的高刚性产物（53-75%）。

  DOI：

  10.1039/c3cc40757h

文献信息

• Conformationally restricted pyrrolidines by intramolecular [2+2] photocycloaddition reactions
  作者：Diego A. Fort、Thomas J. Woltering、Matthias Nettekoven、Henner Knust、Thorsten Bach

  DOI：10.1039/c3cc40757h

  日期：——

  Intramolecular [2+2] photocycloaddition reactions of diversely substituted N-Boc protected 4-(allylaminomethyl)-2(5H)-furanones resulted in rigid products (53–75%) with three spatially defined positions for further functionalisation.

  多种取代的N-Boc保护的4-(烯丙胺甲基)-2(5H)-呋喃酮的分子内[2+2]光环加成反应，产生具有三个空间上定义的位置供进一步功能化的高刚性产物（53-75%）。
• Photochemical Reactions of Prop-2-enyl and Prop-2-ynyl Substituted 4-Aminomethyl- and 4-Oxymethyl-2(5H)-furanones
  作者：Thorsten Bach、Diego A. Fort、Thomas J. Woltering、André M. Alker

  DOI：10.3987/com-13-s(s)67

  日期：——

  Compounds with a heterocyclic 9-oxatricyclo[5.3.0.0(1,5)]decan-8-one skeleton were synthesized by intramolecular [2+2] photocycloaddition reactions of the title compounds (lambda = 254 nm, Et2O or MeCN as the solvent). Starting from various substituted 4-(prop-2-enylaminomethyl)-2(5H)-furanones, products 5, 9, 18, 21, 23, 24 were obtained, which bear a nitrogen atom in position 3 of this skeleton within a pyrrolidine ring. The Boc or Cbz groups represent suitable nitrogen protecting groups, which were compatible with the irradiation conditions and which can be easily cleaved. In an analogous fashion an oxygen (product 22) and carbon substituent (product 25) could be implemented at position 3 of the product if the starting material was appropriately chosen. The prop-2-ynyl substituted substrates did not produce a [2+2] photocycloaddition product but rather underwent a cyclization to spiro products 11 and 13.