1-<(benzyloxy)amino>-2-methylenecyclopentane | 130595-08-3

• 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: 1-<(benzyloxy)amino>-2-methylenecyclopentane
• 英文别名: 2-methylidene-N-phenylmethoxycyclopentan-1-amine
• CAS: 130595-08-3
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: IVDCNSADIRWSJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-hexynal O-benzyl oxime 在 偶氮二异丁腈 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 苯 为溶剂， 生成 1-<(benzyloxy)amino>-2-methylenecyclopentane
  参考文献：
  名称：

  末端炔烃与肟醚的自由基环化

  摘要：

  拴在末端炔烃上的苄基肟醚可有效地进行自由基加氢甲氧基化反应，得到带有受保护胺和乙烯基锡烷官能团的五元和六元环。随后将这些产物进行炔丙基甲酸酯化，以获得未取代的外亚甲基化合物。

  DOI：

  10.1016/s0040-4039(00)97455-0

文献信息

• Tributyltin Hydride-Mediated Free-Radical Cyclization of Allene-Tethered Oxime Ethers and Hydrazones
  作者：José Marco-Contelles、Geneviève Balme、Didier Bouyssi、Christine Destabel、Christiane D. Henriet-Bernard、J. Grimaldi、Jacques M. Hatem

  DOI：10.1021/jo962225r

  日期：1997.3.1

  In this work, we have shown that the tributyltin hydride-mediated cycloisomerization of allene-tethered oxime ethers or hydrazones is a convenient method for the preparation of (vinylstannyl)cyclopentylamine derivatives in terms of simplicity and chemical yields. As a result, the first and detailed analysis of the tributyltin hydride-mediated free-radical cyclization of alkyl-substituted allene-tethered oxime ethers and hydrazones is reported. The site-directed intermolecular attack of the tributyltin radical at the allene moiety and the final size of the ring after cyclization depends on the type of substitution in the substrate. Some general trends can be observed: (1) In crowded substrates having full substitution at C beta or at the terminal-trigonal carbon, the steric hindrance favors attack at the digonal carbon. (2) When different positions in the allene are free for attack, the kinetically more favored irreversible mode of cyclizations (5-exo > 6-exo > 6-endo) determines the ratio of isomers or the final size of the ring. Finally, after acid hydrolysis of the vinyltin products,the resulting O-methyl- or O-benzyl(hydroxylamino)cycloalkanes have been obtained in good yield.
• ENHOLM, ERIC J.;BURROFF, J. A.;JARAMILLO, LUZ M., TETRAHEDRON LETT., 31,(1990) N6, C. 3727-3730
  作者：ENHOLM, ERIC J.、BURROFF, J. A.、JARAMILLO, LUZ M.

  DOI：——

  日期：——
• Free radical cyclizations of terminal alkynes with oxime ethers
  作者：Eric J. Enholm、J.A. Burroff、Luz M. Jaramillo

  DOI：10.1016/s0040-4039(00)97455-0

  日期：——

  A benzyl oxime ether tethered to a terminal alkyne efficiently undergoes a free radical hydrostannylation reaction to afford five- and six-membered rings bearing a protected amine and a vinyl stannane functionality. These products were subsequently protiodestannylated to obtain the unsubstituted exo-methylene compounds.

  拴在末端炔烃上的苄基肟醚可有效地进行自由基加氢甲氧基化反应，得到带有受保护胺和乙烯基锡烷官能团的五元和六元环。随后将这些产物进行炔丙基甲酸酯化，以获得未取代的外亚甲基化合物。