2-benzoyl-3-(1-methyl-1H-indol-3-yl)acrylonitrile | 638145-14-9

• 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: 2-benzoyl-3-(1-methyl-1H-indol-3-yl)acrylonitrile
• 英文别名: 2-Benzoyl-3-(1-methylindol-3-yl)prop-2-enenitrile
• CAS: 638145-14-9
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: YLRRMAJEVCGXRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzoyl-3-(1-methyl-1H-indol-3-yl)acrylonitrile 、 丁烯酮 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以96%的产率得到3-acetyl-4-(1-methyl-1H-indol-3-yl)-6-phenyl-3,4-dihydro-2H-pyran-5-carbonitrile
  参考文献：
  名称：

  Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans

  摘要：

  A novel tandem cross-Rauhut-Currier/cyclization reaction between alpha,beta-unsaturated ketones was developed. Using DABCO (20 mol %) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.036
• 作为产物：
  描述：

  苯甲酸乙酯 在 哌啶 、 sodium hydride 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 19.0h， 生成 2-benzoyl-3-(1-methyl-1H-indol-3-yl)acrylonitrile
  参考文献：
  名称：

  Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans

  摘要：

  A novel tandem cross-Rauhut-Currier/cyclization reaction between alpha,beta-unsaturated ketones was developed. Using DABCO (20 mol %) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.036

文献信息

• DABCO catalyzed cross-Rauhut–Currier/transesterification reactions of activated alkenes with phenyl acrylates: scope and mechanistic insight
  作者：Wen Liu、Gang Zhao

  DOI：10.1039/c3ob41763h

  日期：——

  DABCO catalyzed the cross-Rauhut–Currier/transesterification reaction of α-cyano-α,β-unsaturated ketones and aryl acrylates was discovered. The reaction rate law was determined by an integral method under pseudo-first-order reaction conditions, which assisted in proposing the mechanism of cross-Rauhut–Currier reaction promoted by Brønsted acid and establishing the rate-determining step.

  发现 DABCO 催化 α-氰基-α、β-不饱和酮和丙烯酸芳基酯的交叉 Rauhut 柯里尔/酯交换反应。在准一级反应条件下，采用积分法确定了反应速率规律，有助于提出布伦斯台德酸促进的交叉Rauhut-柯里尔反应的机理，并建立了速率决定步骤。
• Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans
  作者：Wen Liu、Jing Zhou、Changwu Zheng、Xingkuan Chen、Hua Xiao、Yingquan Yang、Yinlong Guo、Gang Zhao

  DOI：10.1016/j.tet.2011.01.036

  日期：2011.3

  A novel tandem cross-Rauhut-Currier/cyclization reaction between alpha,beta-unsaturated ketones was developed. Using DABCO (20 mol %) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies. (C) 2011 Elsevier Ltd. All rights reserved.