1-(5,6-dihydro-4H-pyran-2-yl)-3-phenyl-propenone | 649570-49-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(5,6-dihydro-4H-pyran-2-yl)-3-phenyl-propenone
• 英文别名: (E)-2-[2-(phenyl)-1-ethylenecarbonyl]-5,6-dihydro-4H-pyran；(E)-1-(3,4-dihydro-2H-pyran-6-yl)-3-phenylprop-2-en-1-one
• CAS: 649570-49-0
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: YBKHUCCRHKHEQK-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5,6-dihydro-4H-pyran-2-yl)-3-phenyl-propenone 在 1,3-bis(trifluoromethyl)dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 7.5h， 以78%的产率得到5-phenyl-3,4,5,6-tetrahydrocyclopenta[b]pyran-7(2H)-one
  参考文献：
  名称：

  Iodolium salts as halogen-bond donor catalysts in the Nazarov cyclization: the molecular oxygen enigma

  摘要：

  在碘离子催化下，活化前体的Nazarov环化反应可以在氧气存在的情况下实现，以进行催化剂的激活和周转。

  DOI：

  10.1039/d2nj02731c
• 作为产物：
  描述：

  1-(5,6-dihydro-4H-pyran-2-yl)-3-phenyl-prop-2-en-1-ol 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 以80%的产率得到1-(5,6-dihydro-4H-pyran-2-yl)-3-phenyl-propenone
  参考文献：
  名称：

  Efficient Nazarov Cyclizations of 2-Alkoxy-1,4-pentadien-3-ones

  摘要：

  [GRAPHICS]Expeditious and high-yielding Nazarov cyclizations of 2-alkoxy-1,4-pentadien-3-ones are described. An example of a catalytic asymmetric Nazarov cyclization is presented.

  DOI：

  10.1021/ol036019z

文献信息

• Catalytic Formal Homo-Nazarov Cyclization
  作者：Filippo De Simone、Julien Andrès、Riccardo Torosantucci、Jérôme Waser

  DOI：10.1021/ol802970g

  日期：2009.2.19

  The first catalytic method for the cyclization of vinyl-cyclopropyl ketones (formal homo-Nazarov reaction) is reported. Starting from activated cyclopropanes, heterocyclic, and carbocyclic compounds were obtained under mild conditions using Bronsted acid catalysts. Preliminary investigation of the reaction mechanism indicated a stepwise process.
• 4-Toluenesulfonic acid: an environmentally benign catalyst for Nazarov cyclizations
  作者：Mukkanti Amere、Jérôme Blanchet、Marie-Claire Lasne、Jacques Rouden

  DOI：10.1016/j.tetlet.2008.02.091

  日期：2008.4

  An efficient metal-free catalytic protocol for the electrocyclization of alpha-alkoxydienones to cyclopentenones (Nazarov reaction) in near to quantitative yields is described. The key parameters are the use of inexpensive 4-toluenesulfonic acid in 5 mol % at room temperature in acetonitrile or under solvent-free conditions. The versatility of the transformation is demonstrated with unpolarized dienones with good regioselectivities and excellent yields. (c) 2008 Elsevier Ltd. All rights reserved.
• Efficient Nazarov Cyclizations of 2-Alkoxy-1,4-pentadien-3-ones
  作者：Guangxin Liang、Stefan N. Gradl、Dirk Trauner

  DOI：10.1021/ol036019z

  日期：2003.12.1

  [GRAPHICS]Expeditious and high-yielding Nazarov cyclizations of 2-alkoxy-1,4-pentadien-3-ones are described. An example of a catalytic asymmetric Nazarov cyclization is presented.
• Iodolium salts as halogen-bond donor catalysts in the Nazarov cyclization: the molecular oxygen enigma
  作者：Avery J. To、Graham K. Murphy

  DOI：10.1039/d2nj02731c

  日期：——

  Nazarov cyclizations of activated precurosrs are achieved under iodolium catalysis, provided that oxygen is present for catalyst activation and turnover.

  在碘离子催化下，活化前体的Nazarov环化反应可以在氧气存在的情况下实现，以进行催化剂的激活和周转。