4-(2-Methoxy-ethyl)-5-phenethyl-cyclopent-4-ene-1,3-dione | 56886-87-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-Methoxy-ethyl)-5-phenethyl-cyclopent-4-ene-1,3-dione
• 英文别名: 4-(2-Methoxyethyl)-5-(2-phenylethyl)cyclopent-4-ene-1,3-dione；4-(2-methoxyethyl)-5-(2-phenylethyl)cyclopent-4-ene-1,3-dione
• CAS: 56886-87-4
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: LFUDDBNDQRFRBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-Methoxy-ethyl)-5-phenethyl-cyclopent-4-ene-1,3-dione 生成 (1R,3S,4R,5S)-4-(2-Methoxy-ethyl)-5-phenethyl-cyclopentane-1,3-diol
  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
• 作为产物：
  描述：

  magnesium,ethylbenzene,bromide 、 3,5,5-Trimethoxy-2-(2-methoxy-ethyl)-cyclopent-2-enone 生成 4-(2-Methoxy-ethyl)-5-phenethyl-cyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  环戊酮-XVI：前列腺素的合成，涉及2,3-二烷基-4-羟基-2-环戊烯酮的催化加氢

  摘要：

  具有不同官能化侧链的2，3-二烷基-4-羟基-2-环戊烯酮在催化加氢时主要产生全顺式2，3-二烷基-1，4-二羟基环戊烷。C-12的差向异构体（PG编号）导致前列腺素合成子。描述了侧链功能对这些反应的影响。

  DOI：

  10.1016/0040-4020(76)80117-2

文献信息

• Cyclopentanones—XVI
  作者：P. De Clercq、R. Coen、E. Van Hoof、M. Vandewalle

  DOI：10.1016/0040-4020(76)80117-2

  日期：1976.1

  2,3-Dialkyl-4-hydroxy-2-cyclopentenones with differently functionalised side chains yield predominantly all-cis 2,3-dialkyl-1-4,-dihydroxycyclopentanes on catalytic hydrogenation. Epimerisation at C-12 (PG numbering) leads to prostaglandin synthons. Influence of the side-chain functions on these reactions is described.

  具有不同官能化侧链的2，3-二烷基-4-羟基-2-环戊烯酮在催化加氢时主要产生全顺式2，3-二烷基-1，4-二羟基环戊烷。C-12的差向异构体（PG编号）导致前列腺素合成子。描述了侧链功能对这些反应的影响。
• 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.