3-acetyl-4,6-diphenyl-3,4-dihydro-2H-pyran-5-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-acetyl-4,6-diphenyl-3,4-dihydro-2H-pyran-5-carbonitrile
• 英文别名: (3R,4S)-3-acetyl-4,6-diphenyl-3,4-dihydro-2H-pyran-5-carbonitrile
• 化学式: C₂₀H₁₇NO₂
• 分子量: 303.36
• InChiKey: METLMUKYXQPMPC-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲酸乙酯 在 哌啶 、 三乙烯二胺 、 sodium hydride 、 溶剂黄146 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 31.0h， 生成 3-acetyl-4,6-diphenyl-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

文献信息

• 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.