1-allyl-1-benzyloxycarbonyl-2-benzyloxycarbonyl hydrazine | 1174758-20-3

• 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-allyl-1-benzyloxycarbonyl-2-benzyloxycarbonyl hydrazine
• 英文别名: benzyl N-(phenylmethoxycarbonylamino)-N-prop-2-enylcarbamate
• CAS: 1174758-20-3
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: NIFYSSONKJKKMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  环氧丁烯 、 1-allyl-1-benzyloxycarbonyl-2-benzyloxycarbonyl hydrazine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide] 、 四丁基溴化铵 作用下， 以 乙腈 为溶剂， 反应 20.17h， 以79%的产率得到1-allyl-1-benzyloxycarbonyl-2-((R)-1-hydroxymethylallyl)-2-benzyloxycarbonyl hydrazine
  参考文献：
  名称：

  Dynamic Kinetic Asymmetric Allylation of Hydrazines and Hydroxylamines

  摘要：

  Hydrazines and hydroxylamines have been found to be excellent nucleophiles for the palladium-catalyzed dynamic asymmetric allylic amination of vinyl epoxide, with good yields and enantioselectivities of up to 97% ee. This method is applicable to acyclic and heterocyclic amines and was applied toward a five-step synthesis of (R)-piperazic acid.

  DOI：

  10.1021/ol901185d
• 作为产物：
  描述：

  聯胺 、 3-溴丙烯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以57%的产率得到1-allyl-1-benzyloxycarbonyl-2-benzyloxycarbonyl hydrazine
  参考文献：
  名称：

  Dynamic Kinetic Asymmetric Allylation of Hydrazines and Hydroxylamines

  摘要：

  Hydrazines and hydroxylamines have been found to be excellent nucleophiles for the palladium-catalyzed dynamic asymmetric allylic amination of vinyl epoxide, with good yields and enantioselectivities of up to 97% ee. This method is applicable to acyclic and heterocyclic amines and was applied toward a five-step synthesis of (R)-piperazic acid.

  DOI：

  10.1021/ol901185d

文献信息

• Dynamic Kinetic Asymmetric Allylation of Hydrazines and Hydroxylamines
  作者：Ian Mangion、Neil Strotman、Michael Drahl、Jason Imbriglio、Erin Guidry

  DOI：10.1021/ol901185d

  日期：2009.8.6

  Hydrazines and hydroxylamines have been found to be excellent nucleophiles for the palladium-catalyzed dynamic asymmetric allylic amination of vinyl epoxide, with good yields and enantioselectivities of up to 97% ee. This method is applicable to acyclic and heterocyclic amines and was applied toward a five-step synthesis of (R)-piperazic acid.