(E)-4-(tert-butyldiphenylsilyloxy)but-1-enyl benzyl carbamate | 1382033-80-8

• 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: (E)-4-(tert-butyldiphenylsilyloxy)but-1-enyl benzyl carbamate
• 英文别名: benzyl N-[(E)-4-[tert-butyl(diphenyl)silyl]oxybut-1-enyl]carbamate
• CAS: 1382033-80-8
• 化学式: C₂₈H₃₃NO₃Si
• 分子量: 459.66
• InChiKey: DEDNPVOGFIRJFK-FYJGNVAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(tert-butyldiphenylsilyloxy)but-1-enyl benzyl carbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以86%的产率得到(E)-4-hydroxy-but-1-enyl benzyl carbamate
  参考文献：
  名称：

  Photoredox-Induced Three-Component Oxy-, Amino-, and Carbotrifluoromethylation of Enecarbamates

  摘要：

  A photoredox-catalzyed trifluoromethylation of enecarbamates process is reported. This pathway uses Togni's reagent as the CF3 source and follows a radical/cationic pathway. Under the optimized conditions using [Ru(bpy)(3)(PF6)(2)] as the photocatalyst, a wide range of substituted enecarbamates can readily be difunctionalized by means of various O, N, and C nudeophiles.

  DOI：

  10.1021/ol500374e
• 作为产物：
  描述：

  4-tert-butyldiphenylsilyloxy-1-butene 在 吡啶 、 sodium azide 、 Hoveyda-Grubbs catalyst second generation 、 对苯二酚 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 18.5h， 生成 (E)-4-(tert-butyldiphenylsilyloxy)but-1-enyl benzyl carbamate
  参考文献：
  名称：

  Photoredox-Induced Three-Component Oxy-, Amino-, and Carbotrifluoromethylation of Enecarbamates

  摘要：

  A photoredox-catalzyed trifluoromethylation of enecarbamates process is reported. This pathway uses Togni's reagent as the CF3 source and follows a radical/cationic pathway. Under the optimized conditions using [Ru(bpy)(3)(PF6)(2)] as the photocatalyst, a wide range of substituted enecarbamates can readily be difunctionalized by means of various O, N, and C nudeophiles.

  DOI：

  10.1021/ol500374e

文献信息

• Chiral Phosphoric Acid Catalyzed [3 + 2] Cycloaddition and Tandem Oxidative [3 + 2] Cycloaddition: Asymmetric Synthesis of Substituted 3-Aminodihydrobenzofurans
  作者：Coralie Gelis、Mathieu Bekkaye、Clément Lebée、Florent Blanchard、Géraldine Masson

  DOI：10.1021/acs.orglett.6b01593

  日期：2016.7.15

  Asymmetric [3 + 2] cycloaddition of quinones with ene- and thioene-carbamates was achieved by chiral phosphoric acid catalysis, providing the corresponding 3-amino-2,3-dihydrobenzofurans in excellent yields with moderate to good diastereoselectivities and excellent enantioselectivities. An asymmetric tandem oxidative cycloaddition protocol starting from hydroquinones was also accomplished with phenyliodine(III)

  通过手性磷酸催化可实现醌与烯属和硫代氨基甲酸酯的不对称[3 + 2]环加成反应，从而以优异的产率提供相应的3-氨基-2,3-二氢苯并呋喃，并具有中等至良好的非对映选择性和出色的对映选择性。从对苯二酚开始的不对称串联氧化环加成方案也可以在同一反应容器中用二乙酸苯基碘（III）和手性磷酸完成。
• Iron Chloride‐Catalyzed Three‐Component Domino Sequences: Syntheses of Functionalized α‐Oxy‐<i>N</i>‐acylhemiaminals and α‐Oxyimides
  作者：Fleur Drouet、Jieping Zhu、Géraldine Masson

  DOI：10.1002/adsc.201300847

  日期：2013.12.16

  AbstractThe iron(III) chloride‐multicatalyzed dioxygenation of enamides with TEMPO in the presence of alcohols has been developed. This multicomponent domino process affords efficient new strategies for the synthesis of α‐oxy‐N‐acylhemiaminals or α‐oxyimides in good to excellent yields under mild conditions.magnified image