O-benzyl vinyl acetohydroxamate | 101989-25-7

• 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: O-benzyl vinyl acetohydroxamate
• 英文别名: N-phenylmethoxybut-3-enamide
• CAS: 101989-25-7
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: OBSMDIHCFOFXCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-methyl (4-(trityloxy)but-2-en-1-yl)carbonate 、 O-benzyl vinyl acetohydroxamate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 C₃₇H₃₂NO₃P 、 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(benzyloxy)-6-[(trityloxy)methyl]-3,6-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  Enantioselective Iridium-Catalyzed Allylic Substitutions with Hydroxamic Acid Derivatives as N-Nucleophiles

  摘要：

  Enantioselective Ir-catalyzed allylic aminations with hydroxamic acid derivatives are described. Catalysts were prepared in situ from [Ir(cod)Cl](2) or [Ir(dbcot)Cl](2), a phosphoramidite and base. In addition, pure (pi-allyl)Ir complexes containing cod or dbcot as auxiliary ligands were used. Very high degrees of regio- and enantioselectivity were achieved. The reaction products were transformed Into piperidine derivatives suited as precursors for aza-sugars.

  DOI：

  10.1021/ol200688d
• 作为产物：
  描述：

  乙烯基乙酸 、 O-苄基羟胺 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 O-benzyl vinyl acetohydroxamate
  参考文献：
  名称：

  Oxidative cyclization of β,γ-unsaturated O-acyl hydroxamates to β-lactams

  摘要：

  DOI：

  10.1016/s0040-4039(00)98214-5

文献信息

• RAJENDRA, G.;MILLER, M. J., TETRAHEDRON LETT., 1985, 26, N 44, 5385-5388
  作者：RAJENDRA, G.、MILLER, M. J.

  DOI：——

  日期：——
• Oxidative cyclization of β,γ-unsaturated O-acyl hydroxamates to β-lactams
  作者：G. Rajendra、Marvin J. Miller

  DOI：10.1016/s0040-4039(00)98214-5

  日期：1985.1
• Enantioselective Iridium-Catalyzed Allylic Substitutions with Hydroxamic Acid Derivatives as N-Nucleophiles
  作者：Martin Gärtner、Mascha Jäkel、Manuel Achatz、Christoph Sonnenschein、Olena Tverskoy、Günter Helmchen

  DOI：10.1021/ol200688d

  日期：2011.6.3

  Enantioselective Ir-catalyzed allylic aminations with hydroxamic acid derivatives are described. Catalysts were prepared in situ from [Ir(cod)Cl](2) or [Ir(dbcot)Cl](2), a phosphoramidite and base. In addition, pure (pi-allyl)Ir complexes containing cod or dbcot as auxiliary ligands were used. Very high degrees of regio- and enantioselectivity were achieved. The reaction products were transformed Into piperidine derivatives suited as precursors for aza-sugars.