benzyl (1-(furan-2-yl)allyl)carbamate | 1240563-31-8

• 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 (1-(furan-2-yl)allyl)carbamate
• CAS: 1240563-31-8
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: UOXFCIKDWCSBLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51.47
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl (1-(furan-2-yl)allyl)carbamate 、 丁烯酮 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以69%的产率得到(E)-benzyl (1-(furan-2-yl)-4-oxopent-2-en-1-yl)carbamate
  参考文献：
  名称：

  Substituted Pyrroles via Olefin Cross-Metathesis

  摘要：

  Olefin cross-metathesis (CM) provides a short and convenient entry to diverse trans-gamma-aminoenones. When exposed to either acid or Heck arylation conditions, these intermediates are converted to mono-, di-, or trisubstituted pyrroles. The value of this chemistry is demonstrated by its application to the tetrasubstituted pyrrole subunit of Atorvastatin.

  DOI：

  10.1021/ol101681r
• 作为产物：
  描述：

  benzyl N-[benzenesulfonyl(furan-2-yl)methyl]carbamate 、 乙烯基溴化镁 以 四氢呋喃 为溶剂， 反应 2.75h， 以59%的产率得到benzyl (1-(furan-2-yl)allyl)carbamate
  参考文献：
  名称：

  Substituted Pyrroles via Olefin Cross-Metathesis

  摘要：

  Olefin cross-metathesis (CM) provides a short and convenient entry to diverse trans-gamma-aminoenones. When exposed to either acid or Heck arylation conditions, these intermediates are converted to mono-, di-, or trisubstituted pyrroles. The value of this chemistry is demonstrated by its application to the tetrasubstituted pyrrole subunit of Atorvastatin.

  DOI：

  10.1021/ol101681r

文献信息

• Iridium(I)-Catalyzed Regio- and Enantioselective Decarboxylative Allylic Amidation of Substituted Allyl Benzyl Imidodicarbonates
  作者：Om V. Singh、Hyunsoo Han

  DOI：10.1021/ja067966g

  日期：2007.1.1

  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.