1-allyl-1-benzyloxycarbonyl-2-((R)-1-hydroxymethylallyl)-2-benzyloxycarbonyl hydrazine | 1174758-26-9

• 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-((R)-1-hydroxymethylallyl)-2-benzyloxycarbonyl hydrazine
• 英文别名: benzyl N-[(2R)-1-hydroxybut-3-en-2-yl]-N-[phenylmethoxycarbonyl(prop-2-enyl)amino]carbamate
• CAS: 1174758-26-9
• 化学式: C₂₃H₂₆N₂O₅
• 分子量: 410.47
• InChiKey: BTIPVRAZOJHUBE-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  79.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-allyl-1-benzyloxycarbonyl-2-((R)-1-hydroxymethylallyl)-2-benzyloxycarbonyl hydrazine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 61.0h， 以91%的产率得到(R)-3-hydroxymethyl-3,6-dihydropyridazine-1,2-dicarboxylic acid dibenzyl ester
  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：

  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

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.