benzyl cinnamyl imidodicarbonate | 927837-50-1

• 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: benzyl cinnamyl imidodicarbonate
• 英文别名: [(E)-3-phenylprop-2-enyl] N-phenylmethoxycarbonylcarbamate
• CAS: 927837-50-1
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: FETJXQFVEVSNIJ-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl cinnamyl imidodicarbonate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 chiral phosphoramidite ligand potassium hydride 、 1,8-双二甲氨基萘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (S)-(-)-N-benzyloxycarbonyl-2-phenyl-2,5-dihydropyrrole
  参考文献：
  名称：

  Iridium(I)-Catalyzed Regio- and Enantioselective Decarboxylative Allylic Amidation of Substituted Allyl Benzyl Imidodicarbonates

  摘要：

  The first Ir(I)-catalyzed decarboxylative allylic amidation of allyl benzyl imidodicarbonates is described. The reaction requires Ir(I), chiral phosphoramidite ligand, and DBU as well as proton sponge, and proceeds with excellent regio- and enantioselectivities to afford the branched 1-(aryl/alkyl)-1-benzyloxycarbonylaminoprop-2-ene in good to excellent yields. The scope, mechanism, and synthetic applications of the developed catalytic reaction are discussed.

  DOI：

  10.1021/ja067966g
• 作为产物：
  描述：

  benzyloxycarbonyl isocyanate 、 3-苯基丙-2-烯-1-醇 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到benzyl cinnamyl imidodicarbonate
  参考文献：
  名称：

  Iridium(I)-Catalyzed Regio- and Enantioselective Decarboxylative Allylic Amidation of Substituted Allyl Benzyl Imidodicarbonates

  摘要：

  The first Ir(I)-catalyzed decarboxylative allylic amidation of allyl benzyl imidodicarbonates is described. The reaction requires Ir(I), chiral phosphoramidite ligand, and DBU as well as proton sponge, and proceeds with excellent regio- and enantioselectivities to afford the branched 1-(aryl/alkyl)-1-benzyloxycarbonylaminoprop-2-ene in good to excellent yields. The scope, mechanism, and synthetic applications of the developed catalytic reaction are discussed.

  DOI：

  10.1021/ja067966g