4-(1-Methyl-4-oxocyclohex-2-en-1-yl)butanal | 161618-78-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1-Methyl-4-oxocyclohex-2-en-1-yl)butanal
• CAS: 161618-78-6
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: BIGAWXGMWVJRFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(1-Methyl-4-oxocyclohex-2-en-1-yl)butanal 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 12.0h， 以62%的产率得到(+/-)-endo-5-hydroxy-1-methylbicyclo<4.3.1>decan-7-one
  参考文献：
  名称：

  Free Radical Approach to Directed Aldol-Type Reactions Promoted by Allylic O-Stannyl Ketyls

  摘要：

  DOI：

  10.1021/jo00110a009
• 作为产物：
  描述：

  2,2-Ethylenedioxy-4aβ-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene 在 sodium tetrahydroborate 、 草酰氯 、 水 、 草酸 、 臭氧 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 4-(1-Methyl-4-oxocyclohex-2-en-1-yl)butanal
  参考文献：
  名称：

  Free Radical Approach to Directed Aldol-Type Reactions Promoted by Allylic O-Stannyl Ketyls

  摘要：

  DOI：

  10.1021/jo00110a009

文献信息

• 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.
• Free Radical Approach to Directed Aldol-Type Reactions Promoted by Allylic O-Stannyl Ketyls
  作者：Eric J. Enholm、Yongping Xie、Khalil A. Abboud

  DOI：10.1021/jo00110a009

  日期：1995.3