1-phenyl-2-ethyl-1-penten-3-one

• 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-phenyl-2-ethyl-1-penten-3-one
• 英文别名: 4-benzylidenehexan-3-one
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: BAQMTDVOXXANNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4-[Hydroxy(phenyl)methyl]hexan-3-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.5h， 以53%的产率得到1-phenyl-2-ethyl-1-penten-3-one
  参考文献：
  名称：

  通过烯丙基邻锡烷基酮基的分子间羟醛反应

  摘要：

  α，β-不饱和酮与三丁基锡自由基的温和中性自由基反应产生了共振稳定的烯丙基O-锡烷基酮基中间体。接下来，通过随后的氢原子转移生成的锡（IV）烯醇锡，再用各种醛淬灭，生成羟醛产物，可以很容易地用对甲苯磺酸消除，得到新的α/β-不饱和酮，其E / Z比最高为> 100：1。

  DOI：

  10.1016/0040-4039(95)01999-x

文献信息

• Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups
  作者：Bhanudas Dattatray Mokar、Prakash D. Jadhav、Y. B. Pandit、Rai-Shung Liu

  DOI：10.1039/c8sc00986d

  日期：——

  This work reports new (4 + 2)-annulations of α-alkyl vinylgold carbenes with benzisoxazoles to afford 3,4-dihydroquinoline derivatives with high anti-stereoselectivity. The annulations are operable with carbenes in both acyclic and cyclic forms. This reaction sequence involves an initial formation of imines from α-alkylgold carbenes and benzisoxazoles, followed by a novel carbonyl-enamine reaction

  这项工作报告了 α-烷基乙烯基金卡宾与苯并异恶唑的新 (4 + 2)-环化反应，得到具有高抗立体选择性的 3,4-二氢喹啉衍生物。环化可用于无环和环状形式的卡宾。该反应顺序包括从 α-烷基金卡宾和苯并异恶唑开始形成亚胺，然后进行新的羰基-烯胺反应以产生 3,4-二氢喹啉衍生物。该系统展示了α-烷基金卡宾与外部底物的第一个烷基 C-H 反应性。
• Intermolecular aldol reactions via allylic o-stannyl ketyls
  作者：Eric J. Enholm、Paul E. Whitley

  DOI：10.1016/0040-4039(95)01999-x

  日期：1995.12

  A mild and neutral free radical reaction of an α,β-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate. A tin(IV) enolate, produced by subsequent hydrogen atom transfer, was next quenched with various aldehydes to yield an aldol product which was readily eliminated with p-toluenesulfonic acid to afford new α,β-unsaturated ketones with E/Z

  α，β-不饱和酮与三丁基锡自由基的温和中性自由基反应产生了共振稳定的烯丙基O-锡烷基酮基中间体。接下来，通过随后的氢原子转移生成的锡（IV）烯醇锡，再用各种醛淬灭，生成羟醛产物，可以很容易地用对甲苯磺酸消除，得到新的α/β-不饱和酮，其E / Z比最高为> 100：1。
• Reactions of Tin(IV) Enolates Obtained from <i>O</i>-Stannyl Ketyls under Neutral Free Radical Conditions
  作者：Eric J. Enholm、Paul E. Whitley、Yongping Xie

  DOI：10.1021/jo960639e

  日期：1996.1.1

  Under mild and neutral free radical conditions, an alpha,beta-unsaturated ketone reacted with tributyltin hydride to produce an intermediate resonance-stabilized allylic O-stannyl ketyl. Upon subsequent hydrogen atom abstraction, a tin(IV) enolate was afforded which could be quenched with a variety of electrophiles and form new carbon-carbon bonds. Aldehydes react to produce aldol-type products and both intramolecular and intermolecular carbonyl addition reactions were investigated using this strategy. Using similar methodology, the tin(TV) enolate could be quenched in the presence of HMPA with various alkyl halides and alpha,beta-unsaturated carbonyl compounds (Michael accepters) to yield alkylated products in good yields. These reactions represent a very mild regioselective alternative to metal enolate formation which usually requires strong bases such as LDA or strongly reductive dissolving metal conditions to achieve success. New carbon skeletons for natural product synthesis can be readily constructed using this chemically neutral approach.