(S)-3'-acetyl-6'-amino-2'-methyl-2-oxospiro[indoline-3,4'-pyran]-5'-carbonitrile | 302778-17-2

• 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: (S)-3'-acetyl-6'-amino-2'-methyl-2-oxospiro[indoline-3,4'-pyran]-5'-carbonitrile
• 英文别名: (3S)-5'-acetyl-2'-amino-6'-methyl-2-oxospiro[1H-indole-3,4'-pyran]-3'-carbonitrile
• CAS: 302778-17-2
• 化学式: C₁₆H₁₃N₃O₃
• 分子量: 295.298
• InChiKey: CXAUWNQUZMMPGF-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  靛红 在 哌啶 、 2C₆H₁₀NO₂^(1-)*Ba⁽²⁺⁾ 作用下， 以 乙醇 为溶剂， 反应 15.17h， 生成 (S)-3'-acetyl-6'-amino-2'-methyl-2-oxospiro[indoline-3,4'-pyran]-5'-carbonitrile 、 (S)-3'-acetyl-6'-amino-2'-methyl-2-oxospiro[indoline-3,4'-pyran]-5'-carbonitrile
  参考文献：
  名称：

  Amino Acid Salt Catalyzed Asymmetric Addition Reaction of Acetylacetone to Maleimides and 2-(2-Oxoindolin-3-ylidene)malononitriles

  摘要：

  利用天然氨基酸盐在激活1,3-二羰基化合物中的催化潜力进行了探索，发现马来酰亚胺和2-(2-氧代吲哚啉-3-基)丙二腈是良好的亲电试剂，并以优异的产率和适度的光学纯度得到期望的产物。对照实验表明，钡(S)-丙氨酸的二级氨基团对催化活性和对映选择性至关重要，因此揭示了在当前方法中可能存在一种烯胺激活机制。

  DOI：

  10.1055/s-0037-1610713

文献信息

• Enantioselective synthesis of spiro[4<i>H</i>-pyran-3,3′-oxindole] derivatives catalyzed by cinchona alkaloid thioureas: Significant water effects on the enantioselectivity
  作者：Swapna Konda、Satish Jakkampudi、Hadi D. Arman、John C.-G. Zhao

  DOI：10.1080/00397911.2019.1651866

  日期：——

  Abstract An efficient stereoselective three-component reaction for the synthesis of functionalized spiro[4H-pyran-3,3′-oxindole] derivatives was realized through an organocatalyzed domino Knoevenagel/Michael/cyclization reaction using a cinchonidine-derived thiourea as the catalyst. Using water as the additive was found to improve the product ee values significantly. Under the optimized conditions

  摘要 以辛可尼丁衍生的硫脲为催化剂，通过有机催化的多米诺克诺韦纳格尔/迈克尔/环化反应，实现了一种有效的立体选择性三组分反应，用于合成功能化螺[4H-吡喃-3,3'-羟吲哚]衍生物。发现使用水作为添加剂可以显着提高产品ee值。在优化的条件下，靛红、丙二腈和 1,3-二羰基化合物之间的反应以良好的产率 (71–92%) 和中到高的 ee 值 (高达 87% ee) 产生所需的螺吲哚产物。图形概要
• Highly Enantioselective Construction of Spiro[<i>4H</i>-pyran-3,3′-oxindoles] Through a Domino Knoevenagel/Michael/Cyclization Sequence Catalyzed by Cupreine
  作者：Wen-Bing Chen、Zhi-Jun Wu、Qing-Lan Pei、Lin-Feng Cun、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1021/ol1009224

  日期：2010.7.16

  via a domino Knoevenagel/Michael/cyclization sequence with cupreine as catalyst have been developed. A wide range of optically active spiro[4H-pyran-3,3′-oxindoles] were obtained in excellent yields (up to 99%) with good to excellent enantioselectivities (up to 97%) from simple and readily available starting materials under mild reaction conditions. These heterocyclic spirooxindoles will provide promising

  已经开发了通过多米诺Knoevenagel / Michael /环化序列的第一个对映选择性有机催化的二元和三元反应，并以铜嘌呤为催化剂。在温和的条件下，从简单易得的起始原料中，以优异的收率（高达99％）和良好的至优异的对映选择性（高达97％）获得了广泛的旋光螺旋[ 4H -pyran-3,3'-oxindoles]反应条件。这些杂环螺硫辛醇将为化学生物学和药物发现提供有希望的候选物。
• Amino Acid Salt Catalyzed Asymmetric Addition Reaction of Acetylacetone to Maleimides and 2-(2-Oxoindolin-3-ylidene)malononitriles
  作者：Haiyan Wu、Hongxin Liu、Juan Li、Xinhua Li、Hong-Ping Xiao、Jun Jiang

  DOI：10.1055/s-0037-1610713

  日期：2019.6

  The exploration of catalytic potential of natural amino acid salt in activation of 1,3-dicarbonyls was carried out, in which maleimides and 2-(2-oxoindolin-3-ylidene)malononitriles were found to be good electrophiles and afforded the desired products with excellent yield and moderate optical purity. Control experiments showed that the secondary amino group of barium (S)-prolinate is critical to the catalytic activity as well as enantiocontrol, thus revealed an enamine activation mechanism is possible in the present methodology.

  利用天然氨基酸盐在激活1,3-二羰基化合物中的催化潜力进行了探索，发现马来酰亚胺和2-(2-氧代吲哚啉-3-基)丙二腈是良好的亲电试剂，并以优异的产率和适度的光学纯度得到期望的产物。对照实验表明，钡(S)-丙氨酸的二级氨基团对催化活性和对映选择性至关重要，因此揭示了在当前方法中可能存在一种烯胺激活机制。