2-heptylidenecyclohexanone | 72927-87-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-heptylidenecyclohexanone
• 英文别名: 2-Heptyliden-cyclohexanon；2-heptylidenecyclohexan-1-one；(2Z)-2-heptylidenecyclohexan-1-one
• CAS: 72927-87-8
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: CSVZOOMJWBCXPP-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(1-hydroxyheptyl)cyclohexanone 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.5h， 以89%的产率得到2-heptylidenecyclohexanone
  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

• 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。
• Lambert et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1954, vol. 238, p. 251
  作者：Lambert et al.

  DOI：——

  日期：——
• 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.