4-(4-bromophenyl)-6-phenyl-3,4-dihydro-2H-pyran-2-one | 1138326-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-(4-bromophenyl)-6-phenyl-3,4-dihydro-2H-pyran-2-one
• 英文别名: 4-(4-Bromophenyl)-6-phenyl-3,4-dihydropyran-2-one
• CAS: 1138326-15-4
• 化学式: C₁₇H₁₃BrO₂
• 分子量: 329.193
• InChiKey: UPGWYLDPXAHZKA-UHFFFAOYSA-N

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-benzoyl-3-(4-bromophenyl)cyclopropanecarbaldehyde 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 6.0h， 以75%的产率得到4-(4-bromophenyl)-6-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

• A new approach to 4,6-disubstituted-3,4-dihydropyran-2-ones by Domino Michael addition-cyclization reaction under PTC conditions
  作者：Nicoletta Gaggero、Domenico C.M. Albanese、Donatella Nava

  DOI：10.1016/j.tet.2014.09.022

  日期：2014.11

  Domino Michael addition-cyclization reactions of α,β-unsaturated carbonyl compounds with activated 1,3-dithiane-2-carbothioate esters under solid-liquid phase transfer catalysis conditions provide 4,6-disubstituted-3,4-dihydropyran-2-one-3,3-dithioacetals in good chemical yield. Desulfurization proceeds chemoselectively under mild conditions affording 3,4-dihydropyran-2-ones in high yields.

  在固体-液相转移催化条件下，α，β-不饱和羰基化合物与活化的1,3-二硫代-2-碳硫酸酯的多米诺·迈克尔加成环化反应得到4,6-二取代-3,4-二氢吡喃-2-酮-3,3-二硫缩醛的化学收率良好。脱硫在温和的条件下进行化学选择，以高收率得到3,4-二氢吡喃-2-酮。
• 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.
• <i>N</i>-Heterocyclic Carbene Catalyzed Ring Expansion of Formylcyclopropanes: Synthesis of 3,4-Dihydro-α-pyrone Derivatives
  作者：Gong-Qiang Li、Li-Xin Dai、Shu-Li You

  DOI：10.1021/ol9002898

  日期：2009.4.2

  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.