5,5-dimethyl-3-oxo-1-cyclohexene-1-propanaldehyde | 144648-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-dimethyl-3-oxo-1-cyclohexene-1-propanaldehyde
• 英文别名: 3-(5,5-dimethyl-3-oxocyclohex-1-enyl)propanal；3-(5,5-Dimethyl-3-oxocyclohexen-1-yl)propanal
• CAS: 144648-13-5
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: ZVNPOYFYDSDGRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 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：

  5,5-dimethyl-3-oxo-1-cyclohexene-1-propanaldehyde 在 chromium(VI) oxide 、 硫酸 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 3.0h， 生成 7,9,9-trimethyl-1-oxaspiro-<4,5>-6-decen-2-one
  参考文献：
  名称：

  Synthesis of an Allylic Spiro-Lactone

  摘要：

  A synthesis of an allylic spiro-lactone (1) is described. Compound 1 is obtained in 5 steps from dimedone with an overall yield of 8.8%. The main feature of the synthesis is the transformation of compound 3 in 1, which involves an water elimination accompanied by allylic rearrangement and lactonization.

  DOI：

  10.1080/00397919208021553
• 作为产物：
  描述：

  3-methoxy-5,5-dimethyl-cyclohex-2-enone 在 盐酸 、 碘 、 magnesium 、 1,2-二溴乙烷 作用下， 以 丙酮 为溶剂， 反应 41.0h， 生成 5,5-dimethyl-3-oxo-1-cyclohexene-1-propanaldehyde
  参考文献：
  名称：

  Synthesis of an Allylic Spiro-Lactone

  摘要：

  A synthesis of an allylic spiro-lactone (1) is described. Compound 1 is obtained in 5 steps from dimedone with an overall yield of 8.8%. The main feature of the synthesis is the transformation of compound 3 in 1, which involves an water elimination accompanied by allylic rearrangement and lactonization.

  DOI：

  10.1080/00397919208021553

文献信息

• Synthesis of Spiranes by Thiol-Mediated Acyl Radical Cyclization
  作者：Day-Shin Hsu、Chih-Hao Chen、Chi-Wei Hsu

  DOI：10.1002/ejoc.201501305

  日期：2016.1

  A general and efficient method for the preparation of spiro compounds is described. Various enone-aldehydes were exposed to t-dodecanethiol and AIBN at 75 °C in toluene to afford spirocyclic 1,4-diketones in moderate to good yields.

  描述了制备螺环化合物的通用且有效的方法。将各种烯酮醛暴露于 75°C 的甲苯中的叔十二烷硫醇和 AIBN，以中等至良好的产率提供螺环 1,4-二酮。
• Synthesis of an Allylic Spiro-Lactone
  作者：Mauricio Gomes Constantino、Milton Beltrame、Edna Faria de Medeiros、Gil-Valdo Josè da Silva

  DOI：10.1080/00397919208021553

  日期：1992.11

  A synthesis of an allylic spiro-lactone (1) is described. Compound 1 is obtained in 5 steps from dimedone with an overall yield of 8.8%. The main feature of the synthesis is the transformation of compound 3 in 1, which involves an water elimination accompanied by allylic rearrangement and lactonization.