(E)-1-(1-methyl-1H-imidazol-2-yl)-6-triisopropylsilanyloxy-hex-2-en-1-one | 1360556-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-(1-methyl-1H-imidazol-2-yl)-6-triisopropylsilanyloxy-hex-2-en-1-one
• 英文别名: (E)-1-(1-methyl-1H-imidazol-2-yl)-6-((triisopropylsilyl)oxy)hex-2-en-1-one
• CAS: 1360556-62-2
• 化学式: C₁₉H₃₄N₂O₂Si
• 分子量: 350.577
• InChiKey: RMEHPBHBUFLIOT-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-氰基-3-四氢噻吩酮 、 (E)-1-(1-methyl-1H-imidazol-2-yl)-6-triisopropylsilanyloxy-hex-2-en-1-one 在 2,6-双[(3aR,8aS)-(+)-8H-茚[1,2-d]恶唑啉-2-基]吡啶 、 scandium tris(trifluoromethanesulfonate) 、 四丁基氢氧化铵 作用下， 以 氯仿 、 甲醇 为溶剂， 以56%的产率得到3-[2-(1-methyl-1H-imidazol-2-yl)-2-oxoethyl]-2-methylene-6-((triisopropylsilyl)oxy)hexanenitrile
  参考文献：
  名称：

  Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a One-Pot Sequential Asymmetric Michael Addition/Retro-Dieckmann/Retro-Michael Fragmentation Cascade

  摘要：

  A highly enantioselective synthesis of alpha-branched acrylonitriles is reported featuring a one-pot sequential asymmetric Michael addition/retro-Dieckmann/retro-Michael fragmentation cascade. The method, which relies on a solid, bench-stable, and commercially available acrylonitrile surrogate, is practical, scalable, and highly versatile and provides a direct access to a wide range of enantioenriched nitrite-containing building blocks. Most importantly, the method offers a new tool to incorporate an acrylonitrile moiety in an asymmetric fashion.

  DOI：

  10.1021/acs.orglett.0c02079
• 作为产物：
  描述：

  4-((triisopropylsilyl)oxy)butan-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (E)-1-(1-methyl-1H-imidazol-2-yl)-6-triisopropylsilanyloxy-hex-2-en-1-one
  参考文献：
  名称：

  Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a One-Pot Sequential Asymmetric Michael Addition/Retro-Dieckmann/Retro-Michael Fragmentation Cascade

  摘要：

  A highly enantioselective synthesis of alpha-branched acrylonitriles is reported featuring a one-pot sequential asymmetric Michael addition/retro-Dieckmann/retro-Michael fragmentation cascade. The method, which relies on a solid, bench-stable, and commercially available acrylonitrile surrogate, is practical, scalable, and highly versatile and provides a direct access to a wide range of enantioenriched nitrite-containing building blocks. Most importantly, the method offers a new tool to incorporate an acrylonitrile moiety in an asymmetric fashion.

  DOI：

  10.1021/acs.orglett.0c02079

文献信息

• Photocatalytic [2 + 2] Cycloadditions of Enones with Cleavable Redox Auxiliaries
  作者：Elizabeth L. Tyson、Elliot P. Farney、Tehshik P. Yoon

  DOI：10.1021/ol3000298

  日期：2012.2.17

  alpha,beta-Unsaturated 2-imidazolyl ketones undergo [2 + 2] cycloaddition with a variety of Michael acceptors upon irradiation with visible light in the presence of Ru(bpy)(3)(2+). Cleavage of the imidazolyl auxiliary from the cycloadducts affords cyclobutane carboxamides, esters, thioesters, and acids that would not be accessible from direct cycloaddition of the corresponding unsaturated carbonyl compounds.