3,5,5-Triethoxy-2-(2-methoxy-ethyl)-cyclopent-2-enone | 55833-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5,5-Triethoxy-2-(2-methoxy-ethyl)-cyclopent-2-enone
• 英文别名: 3,5,5-Triethoxy-2-(2-methoxyethyl)cyclopent-2-en-1-one；3,5,5-triethoxy-2-(2-methoxyethyl)cyclopent-2-en-1-one
• CAS: 55833-92-6
• 化学式: C₁₄H₂₄O₅
• 分子量: 272.342
• InChiKey: BTXKANXXNOVSFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5,5-Triethoxy-2-(2-methoxy-ethyl)-cyclopent-2-enone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-Hydroxy-3-(2-methoxy-ethyl)-cyclopent-2-enone
  参考文献：
  名称：

  Cyclopentanones; XV¹. Synthesis of 1-Alkyl (or Aryl)-2-hydroxy-3-oxocyclopentenes and of 1-Alkyl (or Aryl)-3,5-dioxocyclopentenes

  摘要：

  DOI：

  10.1055/s-1976-23951
• 作为产物：
  描述：

  4-Hydroxy-5-(2-methoxy-ethyl)-cyclopent-4-ene-1,3-dione 、 原甲酸三乙酯 生成 3,5,5-Triethoxy-2-(2-methoxy-ethyl)-cyclopent-2-enone
  参考文献：
  名称：

  Cyclopentanones. XII. An Alternative Synthesis of Prostaglandins Involving Catalytic Hydrogenation of 2, 3-Dialkyl-4-Dihydroxy-2-Cyclopentenones

  摘要：

  AbstractA novel approach to Corey's aldehyde is described. A suitable substituted all cis 2, 3‐dialkyl‐l, 4‐cyclopentanediol system is obtained by catalytic reduction of 2, 3‐dialkyl‐4‐hydroxy‐2‐cyclopentenones. Epimerisation to the prostaglandin configuration occurs spontaneously when later on the Horner reaction is carried out.

  DOI：

  10.1002/bscb.19750840311

文献信息

• 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. XVII: Prostaglandin synthesis involving the lithium-liquid ammonia reduction of 3-alkyl-4-hydroxy-2-(1′-octynyl)-2-cyclopentenones
  作者：P. De Clercq、M. De Smet、K. Legein、F. Vanhulle、M. Vandewalle

  DOI：10.1002/bscb.19760850706

  日期：——

  AbstractThe present paper describes the lithium‐liquid ammonia reduction of 3‐alkyl‐4‐hydroxy‐2‐(1′‐octynyl)‐2‐cyclopentenones; depending on the nature of the 3‐alkyl side chain prostaglandins of the F1‐series or primary prostaglandins of the 2‐series are synthesised.
• 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. XII. An Alternative Synthesis of Prostaglandins Involving Catalytic Hydrogenation of 2, 3-Dialkyl-4-Dihydroxy-2-Cyclopentenones
  作者：R. Coen、P. De Clercq、D. van Haver、M. Vandewalle

  DOI：10.1002/bscb.19750840311

  日期：——

  AbstractA novel approach to Corey's aldehyde is described. A suitable substituted all cis 2, 3‐dialkyl‐l, 4‐cyclopentanediol system is obtained by catalytic reduction of 2, 3‐dialkyl‐4‐hydroxy‐2‐cyclopentenones. Epimerisation to the prostaglandin configuration occurs spontaneously when later on the Horner reaction is carried out.