ethyl 2-(4-chloro-1-hydroxy-3-oxocyclopent-4-enyl)acetate | 201803-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(4-chloro-1-hydroxy-3-oxocyclopent-4-enyl)acetate
• 英文别名: Ethyl 2-(3-chloro-1-hydroxy-4-oxocyclopent-2-en-1-yl)acetate
• CAS: 201803-07-8
• 化学式: C₉H₁₁ClO₄
• 分子量: 218.637
• InChiKey: CUNUNZFFXJILBA-UHFFFAOYSA-N

物化性质

• 沸点：
  339.3±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-chloro-1-hydroxy-3-oxocyclopent-4-enyl)acetate 在 N,N-二甲基丙烯基脲 、 sodium tetrahydroborate 、 重铬酸吡啶 、 正丁基锂 、 cerium(III) chloride 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.5h， 生成
  参考文献：
  名称：

  Practical Synthesis of (±)-Chlorovulone II

  摘要：

  We describe a total synthesis of (+/-)-chlorovulone II that is 10 steps shorter than the best alternative currently available (nine vs 19 steps). The key event of the synthesis is an aldol addition of the enolate of ethyl acetate into 4-cyclopentene-1,3-dione, a substance that has received little attention as an educt for prostanoid synthesis and for which little is known about carbonyl 1,2-addition with enolates. In addition, we provide chemical and stereochemical details of a route to a key intermediate toward the title compound that involves a carbonyl-ene reaction and a radical addition to an aldehyde carbonyl.

  DOI：

  10.1021/jo972073f
• 作为产物：
  描述：

  ethyl 2-(1-hydroxy-3-oxocyclopent-4-enyl)acetate 在 氯 作用下， 以 四氯化碳 为溶剂， 反应 0.33h， 以77%的产率得到ethyl 2-(4-chloro-1-hydroxy-3-oxocyclopent-4-enyl)acetate
  参考文献：
  名称：

  Practical Synthesis of (±)-Chlorovulone II

  摘要：

  We describe a total synthesis of (+/-)-chlorovulone II that is 10 steps shorter than the best alternative currently available (nine vs 19 steps). The key event of the synthesis is an aldol addition of the enolate of ethyl acetate into 4-cyclopentene-1,3-dione, a substance that has received little attention as an educt for prostanoid synthesis and for which little is known about carbonyl 1,2-addition with enolates. In addition, we provide chemical and stereochemical details of a route to a key intermediate toward the title compound that involves a carbonyl-ene reaction and a radical addition to an aldehyde carbonyl.

  DOI：

  10.1021/jo972073f

文献信息

• Practical Synthesis of (±)-Chlorovulone II
  作者：Marco A. Ciufolini、Shuren Zhu

  DOI：10.1021/jo972073f

  日期：1998.3.1

  We describe a total synthesis of (+/-)-chlorovulone II that is 10 steps shorter than the best alternative currently available (nine vs 19 steps). The key event of the synthesis is an aldol addition of the enolate of ethyl acetate into 4-cyclopentene-1,3-dione, a substance that has received little attention as an educt for prostanoid synthesis and for which little is known about carbonyl 1,2-addition with enolates. In addition, we provide chemical and stereochemical details of a route to a key intermediate toward the title compound that involves a carbonyl-ene reaction and a radical addition to an aldehyde carbonyl.