(E)-tert-butyl 4-(3-(1-methyl-1H-imidazol-2-yl)-3-oxoprop-1-en-1-yl)piperidine-1-carboxylate | 1360556-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (E)-tert-butyl 4-(3-(1-methyl-1H-imidazol-2-yl)-3-oxoprop-1-en-1-yl)piperidine-1-carboxylate
• 英文别名: tert-butyl (E)-4-(3-(1-methyl-1H-imidazol-2-yl)-3-oxoprop-1-en-1-yl)piperidine-1-carboxylate
• CAS: 1360556-63-3
• 化学式: C₁₇H₂₅N₃O₃
• 分子量: 319.404
• InChiKey: JUZRJWXJWYQTLD-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  64.43
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-氰基-3-四氢噻吩酮 、 (E)-tert-butyl 4-(3-(1-methyl-1H-imidazol-2-yl)-3-oxoprop-1-en-1-yl)piperidine-1-carboxylate 在 4,4'-二甲基-2,2'-联吡啶 、 copper(II) bis(trifluoromethanesulfonate) 、 四丁基氢氧化铵 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 0.03h， 生成 tert-butyl 4-(2-cyano-5-(1-methyl-1H-imidazol-2-yl)-5-oxopent-1-en-3-yl)piperidine-1-carboxylate
  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：

  2-氯-1-(1-甲基-1H-咪唑-2-基)乙酮 以 甲苯 、 苯 为溶剂， 生成 (E)-tert-butyl 4-(3-(1-methyl-1H-imidazol-2-yl)-3-oxoprop-1-en-1-yl)piperidine-1-carboxylate
  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.