6-(4-bromophenyl)-4-phenyl-3,4-dihydro-2H-pyran-2-one | 1138326-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-(4-bromophenyl)-4-phenyl-3,4-dihydro-2H-pyran-2-one
• 英文别名: 6-(4-Bromophenyl)-4-phenyl-3,4-dihydropyran-2-one
• CAS: 1138326-18-7
• 化学式: C₁₇H₁₃BrO₂
• 分子量: 329.193
• InChiKey: HJXTVVWJBLSVJL-UHFFFAOYSA-N

物化性质

• 沸点：
  478.4±45.0 °C(predicted)
• 密度：
  1.432±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,2S,3R)-2-(4-bromobenzoyl)-3-phenylcyclopropane-1-carbaldehyde 在 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以73%的产率得到6-(4-bromophenyl)-4-phenyl-3,4-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  N-Heterocyclic Carbene Catalyzed Ring Expansion of Formylcyclopropanes: Synthesis of 3,4-Dihydro-α-pyrone Derivatives

  摘要：

  N-Heterocyclic carbene catalyzed ring expansion of readily accessible 2-acyl-l-formylcyclopropanes was developed. With 5 mol % of triazoliurn salt 5 and 30 mol % of DBU, ring expansion of various 2-acyl-l-formylcyclopropanes led to 3,4-dihydro-alpha-pyrones in good to excellent yields.

  DOI：

  10.1021/ol9002898

文献信息

• Asymmetric Access to the Smallest Enolate Intermediate via Organocatalytic Activation of Acetic Ester
  作者：Shaojin Chen、Lin Hao、Yuexia Zhang、Bhoopendra Tiwari、Yonggui Robin Chi

  DOI：10.1021/ol402877n

  日期：2013.11.15

  An NHC-catalyzed activation of acetic esters to afford enolate intermediates is disclosed. The catalytically generated triazolium enolate intermediates serve as two-carbon nucleophiles that undergo highly enantioselective reactions with enones and alpha,beta-unsaturated imines to give a-unsubstituted delta-lactones and lactams, respectively.