1-cyano-3-(methoxycarbonyl)-1-phenylbut-3-en-1-yl 3-methylbut-2-enoate | 1373932-28-5

• 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: 1-cyano-3-(methoxycarbonyl)-1-phenylbut-3-en-1-yl 3-methylbut-2-enoate
• CAS: 1373932-28-5
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: CGJLDPPWHGLIDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76.39
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-cyano-3-(methoxycarbonyl)-1-phenylbut-3-en-1-yl 3-methylbut-2-enoate 在 三丁基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以41%的产率得到methyl 2-(cyanomethyl)-5-methyl-3-oxo-2-(2-oxo-2-phenylethyl)hex-4-enoate
  参考文献：
  名称：

  Lewis Base Promoted Intramolecular Acylcyanation of α-Substituted Activated Alkenes: Construction of Ketones Bearing β-Quaternary Carbon Centers

  摘要：

  A novel phosphine-promoted intramolecular acylcyanation of alpha-substituted activated alkenes has been developed, which provides a unique access to densely functionalized acyclic ketones bearing beta-quaternary carbon centers with a remarkable feature that both alpha- and beta-positions of activated alkene are functionalized.

  DOI：

  10.1021/ol3007716
• 作为产物：
  描述：

  methyl 2-(((tert-butoxycarbonyl)oxy)methyl)acrylate 、 α-Cyanobenzyl 3-Methyl-2-butenoate 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以86%的产率得到1-cyano-3-(methoxycarbonyl)-1-phenylbut-3-en-1-yl 3-methylbut-2-enoate
  参考文献：
  名称：

  Lewis Base Promoted Intramolecular Acylcyanation of α-Substituted Activated Alkenes: Construction of Ketones Bearing β-Quaternary Carbon Centers

  摘要：

  A novel phosphine-promoted intramolecular acylcyanation of alpha-substituted activated alkenes has been developed, which provides a unique access to densely functionalized acyclic ketones bearing beta-quaternary carbon centers with a remarkable feature that both alpha- and beta-positions of activated alkene are functionalized.

  DOI：

  10.1021/ol3007716

文献信息

• Sulfa-Michael addition initiated one-pot tandem sequence: Construction of highly substituted 2-cyclopentenones from allylic cyanohydrins
  作者：Ling-Cong Jiao、Ze-Ying He、Wei-Wei Liao

  DOI：10.1016/j.tet.2020.130922

  日期：2020.2

  A practical and facile one-pot protocol to construct highly substituted 2-vinyl 2-cyclopentenone derivatives from O-unsaturated acyl-substituted allylic cyanohydrins through a SMA triggered tandem sequence is described. In this process, a SMA triggered intramolecular aldol sequence, followed by a DBU-catalyzed intramolecular Aldol reaction and subsequent dehydroxylation were involved. This one-pot

  描述了一种实用且简便的一锅操作规程，可通过SMA触发的串联序列从O-不饱和酰基取代的烯丙基氰醇构建高度取代的2-乙烯基2-环戊烯酮衍生物。在这个过程中，SMA触发了分子内羟醛醛缩醛的序列，随后是DBU催化的分子内羟醛醛缩合反应和随后的脱羟基作用。在温和的反应条件下，该一锅法转化顺利进行。