ethyl 2-(1-hydroxy-3-oxocyclopent-4-enyl)acetate | 201802-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(1-hydroxy-3-oxocyclopent-4-enyl)acetate
• 英文别名: Ethyl 2-(1-hydroxy-4-oxocyclopent-2-en-1-yl)acetate
• CAS: 201802-91-7
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: OYGJJCXYOLDIGF-UHFFFAOYSA-N

物化性质

• 沸点：
  313.1±42.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 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-(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 、 氯 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.83h， 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-4,4-dimethoxy-2-methylsulfonyloxycyclopentyl)acetate 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以0.55 g的产率得到ethyl 2-(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

• A Paternò−Büchi Approach to the Synthesis of Merrilactone A
  作者：Jone Iriondo-Alberdi、Jesus E. Perea-Buceta、Michael F. Greaney

  DOI：10.1021/ol0514496

  日期：2005.9.1

  A six-step approach to the tetracyclic core of merrilactone A is described that uses an intramolecular Paterno-Buchi photoaddition to install the key oxetane ring. Irradiation of bicyclic enone 16, constructed through cyclopentenone alkylation followed by a domino oxy-/carbopalladation reaction, produces the tetracyclic oxetane 17 in excellent yield, having the core carbon skeleton of the target compound

  描述了一种六步法制备美瑞内酯A的四环核的方法，该方法使用分子内Paterno-Buchi光加成法安装了关键的氧杂环丁烷环。辐射通过环戊烯酮烷基化，然后进行多米诺氧基-/卡巴钯化反应而构成的双环烯酮16，以优异的收率生产出四环氧杂环丁烷17，具有目标化合物Merrilactone A的核心碳骨架。
• 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.