allyl (E)-2-(2'-oxoindolin-3'-ylidene)acetate | 825647-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: allyl (E)-2-(2'-oxoindolin-3'-ylidene)acetate
• 英文别名: 2-Propen-1-yl (2E)-2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)acetate；prop-2-enyl (2E)-2-(2-oxo-1H-indol-3-ylidene)acetate
• CAS: 825647-71-0
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: XFLJLGWWDIFSRA-CSKARUKUSA-N

物化性质

• 沸点：
  441.4±45.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  allyl (E)-2-(2'-oxoindolin-3'-ylidene)acetate 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 Mg(ClO)4 、 三乙胺 、 原甲酸三甲酯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 168.0h， 生成 (3S,3'S,4'R,6'S,8'R,8'aR)-8'-(azocane-1-carbonyl)-6'-[4-(2-hydroxyethoxy)phenyl]-3',4'-diphenylspiro[1H-indole-3,7'-4,6,8,8a-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazine]-1',2-dione
  参考文献：
  名称：

  A Library of Spirooxindoles Based on a Stereoselective Three-Component Coupling Reaction

  摘要：

  A collection of structurally complex and chemically diverse small molecules is a useful tool to explore cell circuitry. In this article, we report the split-pool synthesis of more than 3000 spirooxindoles on high capacity macrobeads. The key reaction to assemble the spirooxindole core stereoselectively is a Lewis acid variant of the Williams' three-component coupling, After formation, the skeleton was elaborated using Sonogashira couplings, amide forming reactions, and N-acylations of gamma-lactams. The final library was analyzed by sampling individual macrobeads and by using binomial confidence limits. It was determined that at least 82% of the library compounds should have better than 80% purity. To demonstrate the utility of our discovery process, a high-throughput chemical genetic modifier screen was performed using stock solutions of the resultant products. A number of positives were identified as enhancers of the cellular actions of latrunculin B, an actin polymerization inhibitor. Through resynthesis, we confirmed one of the positives and demonstrated that, in yeast cells, it has an EC50 in the sub-micromolar range.

  DOI：

  10.1021/ja045089d
• 作为产物：
  描述：

  P,P-二乙基膦酰基乙酸烯丙酯 、 靛红 在 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以44%的产率得到allyl (E)-2-(2'-oxoindolin-3'-ylidene)acetate
  参考文献：
  名称：

  A Library of Spirooxindoles Based on a Stereoselective Three-Component Coupling Reaction

  摘要：

  A collection of structurally complex and chemically diverse small molecules is a useful tool to explore cell circuitry. In this article, we report the split-pool synthesis of more than 3000 spirooxindoles on high capacity macrobeads. The key reaction to assemble the spirooxindole core stereoselectively is a Lewis acid variant of the Williams' three-component coupling, After formation, the skeleton was elaborated using Sonogashira couplings, amide forming reactions, and N-acylations of gamma-lactams. The final library was analyzed by sampling individual macrobeads and by using binomial confidence limits. It was determined that at least 82% of the library compounds should have better than 80% purity. To demonstrate the utility of our discovery process, a high-throughput chemical genetic modifier screen was performed using stock solutions of the resultant products. A number of positives were identified as enhancers of the cellular actions of latrunculin B, an actin polymerization inhibitor. Through resynthesis, we confirmed one of the positives and demonstrated that, in yeast cells, it has an EC50 in the sub-micromolar range.

  DOI：

  10.1021/ja045089d

文献信息

• A Library of Spirooxindoles Based on a Stereoselective Three-Component Coupling Reaction
  作者：Michael M.-C. Lo、Christopher S. Neumann、Satoshi Nagayama、Ethan O. Perlstein、Stuart L. Schreiber

  DOI：10.1021/ja045089d

  日期：2004.12.1

  A collection of structurally complex and chemically diverse small molecules is a useful tool to explore cell circuitry. In this article, we report the split-pool synthesis of more than 3000 spirooxindoles on high capacity macrobeads. The key reaction to assemble the spirooxindole core stereoselectively is a Lewis acid variant of the Williams' three-component coupling, After formation, the skeleton was elaborated using Sonogashira couplings, amide forming reactions, and N-acylations of gamma-lactams. The final library was analyzed by sampling individual macrobeads and by using binomial confidence limits. It was determined that at least 82% of the library compounds should have better than 80% purity. To demonstrate the utility of our discovery process, a high-throughput chemical genetic modifier screen was performed using stock solutions of the resultant products. A number of positives were identified as enhancers of the cellular actions of latrunculin B, an actin polymerization inhibitor. Through resynthesis, we confirmed one of the positives and demonstrated that, in yeast cells, it has an EC50 in the sub-micromolar range.