3,5,5-三乙氧基-2-(3-甲基丁-2-烯-1-基)环戊-2-烯-1-酮 | 54105-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,5,5-三乙氧基-2-(3-甲基丁-2-烯-1-基)环戊-2-烯-1-酮
• 英文名称: 3,5,5-Triethoxy-2-(3-methyl-but-2-enyl)-cyclopent-2-enone
• 英文别名: 2-(3-Methyl-2-butenyl)-3,5,5-triethoxy-2-cyclopenten-1-one；3,5,5-triethoxy-2-(3-methylbut-2-enyl)cyclopent-2-en-1-one
• CAS: 54105-81-6
• 化学式: C₁₆H₂₆O₄
• 分子量: 282.38
• InChiKey: DCPAHKIGIBFKOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  380.5±42.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5,5-三乙氧基-2-(3-甲基丁-2-烯-1-基)环戊-2-烯-1-酮 在 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,3S,4S,5S)-4-(7-Methoxy-heptyl)-5-(3-methyl-butyl)-cyclopentane-1,3-diol
  参考文献：
  名称：

  Cyclopentanones. X A novel synthesis of (dl)-prostaglandin F1α

  摘要：

  AbstractA novel total synthesis of (dl)‐prostaglandin F1α methyl ester is described. The 2,3‐dialkyl‐1,4‐cyclopentanediol system is obtained by the reduction of an appropriate 2,3‐dialkyl‐4‐hydroxy‐2‐cyclopentenone. The facile conversion of the most abundant isomeric cyclopentanediol, with the all trans relation of the four substituents to a δ‐lactone enables the creation of the required prostaglandin configuration and the construction of the C‐12 side chain. Extensive spectroscopic data are included.

  DOI：

  10.1002/bscb.19740830714
• 作为产物：
  描述：

  [3-(3-Methyl-but-2-enyl)-2,4,5-trioxo-cyclopentyl]-oxo-acetic acid ethyl ester 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 3,5,5-三乙氧基-2-(3-甲基丁-2-烯-1-基)环戊-2-烯-1-酮
  参考文献：
  名称：

  Cyclopentanones. X A novel synthesis of (dl)-prostaglandin F1α

  摘要：

  AbstractA novel total synthesis of (dl)‐prostaglandin F1α methyl ester is described. The 2,3‐dialkyl‐1,4‐cyclopentanediol system is obtained by the reduction of an appropriate 2,3‐dialkyl‐4‐hydroxy‐2‐cyclopentenone. The facile conversion of the most abundant isomeric cyclopentanediol, with the all trans relation of the four substituents to a δ‐lactone enables the creation of the required prostaglandin configuration and the construction of the C‐12 side chain. Extensive spectroscopic data are included.

  DOI：

  10.1002/bscb.19740830714

文献信息

• Cyclopentanones; XV¹. Synthesis of 1-Alkyl (or Aryl)-2-hydroxy-3-oxocyclopentenes and of 1-Alkyl (or Aryl)-3,5-dioxocyclopentenes
  作者：W. VAN BRUSSEL、M. VANDEWALLE

  DOI：10.1055/s-1976-23951

  日期：——
• Cyclopentanones XIV. The synthesis of a prostanoid synthon starting from 3-alkyl-1,2,4-cyclopentanetriones
  作者：W. van Brussel、J. van Hooland、P. De Clercq、M. Vandewalle

  DOI：10.1002/bscb.19750840803

  日期：——

  Abstract3‐Alkyl‐1,2,4‐cyclopentanetriones can readily be converted to all trans 2,3‐dialkyl‐1,4‐cyclopentanediols. The latter compounds are intermediates for the synthesis of a prostanoid synthon, known as Corey's lactone, when the alkyl substituents contain appropriate functional groups. The conversion of two different sets of side‐chains to readily distinguishable two‐carbon and one‐carbon aldehyde units is described. Extensive 1H‐NMR data are included.
• Cyclopentanones. X A novel synthesis of (dl)-prostaglandin F1α
  作者：P. De Clercq、M. Vandewalle

  DOI：10.1002/bscb.19740830714

  日期：——

  AbstractA novel total synthesis of (dl)‐prostaglandin F1α methyl ester is described. The 2,3‐dialkyl‐1,4‐cyclopentanediol system is obtained by the reduction of an appropriate 2,3‐dialkyl‐4‐hydroxy‐2‐cyclopentenone. The facile conversion of the most abundant isomeric cyclopentanediol, with the all trans relation of the four substituents to a δ‐lactone enables the creation of the required prostaglandin configuration and the construction of the C‐12 side chain. Extensive spectroscopic data are included.