2-(4-甲氧基苯基)二氢-2H-吡喃-4(3h)-酮 | 1026692-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(4-甲氧基苯基)二氢-2H-吡喃-4(3h)-酮
• 英文名称: (+/-)-2-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-one
• 英文别名: 2-(4-methoxyphenyl)tetrahydro-4H-pyran-4-one；2-(4-methoxyphenyl)dihydro-2H-pyran-4(3H)-one；2-(4-methoxyphenyl)oxan-4-one
• CAS: 1026692-54-5
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: DADYYFMMZDWEEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基苯基)二氢-2H-吡喃-4(3h)-酮 在 Daucus carota cells 作用下， 以 水 为溶剂， 反应 30.0h， 生成 (2R,4S)-2-(4-methoxyphenyl)-tetrahydro-2H-4-pyranol 、 (2R,4R)-2-(4-methoxyphenyl)-tetrahydro-2H-4-pyranol 、 (2S,4R)-2-(4-methoxyphenyl)-tetrahydro-2H-4-pyranol 、 (2S,4S)-2-(4-methoxyphenyl)-tetrahydro-2H-4-pyranol
  参考文献：
  名称：

  Enantioselective reduction of 2-substituted tetrahydropyran-4-ones using Daucus carota plant cells

  摘要：

  Enzymatic reduction of 2-substituted tetrahydropyran-4-ones with Daucus carota, plant cells as biocatalyst occurred in water under extremely mild and environmentally benign conditions giving a 1:1 mixture of diastereoselectively (2R,4S)- and (2S,4S)-2-aryl- or 2-alkyl-tetrahydropyranois in high yields. (c) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.02.131
• 作为产物：
  描述：

  4-((4-methoxybenzyl)oxy)but-1-en-2-yl acetate 在 4-乙酰胺基-2,2,6,6-四甲基哌啶 作用下， 以 乙腈 为溶剂， 反应 1.25h， 以71%的产率得到2-(4-甲氧基苯基)二氢-2H-吡喃-4(3h)-酮
  参考文献：
  名称：

  基于动力学的方法开发慢氧化的电催化变体：在氢化物抽象引发的环化反应中的应用

  摘要：

  通过原位电化学氧化剂再生，可以在无水条件下以亚化学计量的氧代铵离子负载生成氧代碳鎓和酰基亚胺鎓离子。通过使用恒定电位条件可以避免自由基阳离子中间体的分解，并通过阳离子稳定性、氧化剂强度、过电位和反应浓度之间的相互作用来维持电流。

  DOI：

  10.1002/chem.202200335

文献信息

• Mechanistic analysis of oxidative C–H cleavages using inter- and intramolecular kinetic isotope effects
  作者：Hyung Hoon Jung、Paul E. Floreancig

  DOI：10.1016/j.tet.2009.10.088

  日期：2009.12

  series of monodeuterated benzylic and allylic ethers were subjected to oxidative carbon–hydrogen bond cleavage to determine the impact of structural variation on intramolecular kinetic isotope effects in DDQ-mediated cyclization reactions. These values are compared to the corresponding intermolecular kinetic isotope effects that were accessed through subjecting mixtures of non-deuterated and dideuterated

  对一系列单氘代苄基醚和烯丙基醚进行氧化碳氢键断裂，以确定结构变化对 DDQ 介导的环化反应中分子内动力学同位素效应的影响。将这些值与通过将非氘化和双氘化底物的混合物置于反应条件下获得的相应分子间动力学同位素效应进行比较。结果表明，碳氢键断裂是速率决定因素，自由基阳离子很可能是反应机制中的关键中间体。
• A novel self-terminated Prins strategy for the synthesis of tetrahydropyran-4-one derivatives and their behaviour in Fisher indole synthesis
  作者：B. V. Subba Reddy、S. Rehana Anjum、B. Sridhar

  DOI：10.1039/c6ra11218h

  日期：——

  has been developed for the synthesis of 2-substituted tetrahydropyran-4-one derivatives through a condensation of 3-(phenylthio)but-3-en-1-ol with carbonyl compounds in the presence of 5 mol% of Sc(OTf)3 under mild conditions. A few products were subsequently transformed into the corresponding indoles by Fisher-indole synthesis.

  已开发出一种新颖的自封端Prins策略，用于在5 mol存在下通过3-（苯硫基）but-3-en-1-醇与羰基化合物的缩合反应合成2-取代的四氢吡喃-4-酮衍生物。在温和条件下的Sc（OTf）3的百分比。随后通过费希尔-吲哚合成将一些产物转化为相应的吲哚。
• 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone-Catalyzed Reactions Employing MnO₂ as a Stoichiometric Oxidant
  作者：Lei Liu、Paul E. Floreancig

  DOI：10.1021/ol102078v

  日期：2010.10.15

  Several oxidative reactions can be effected with MnO2 in the presence of substoichiometric quantities of DDQ. These transformations include oxidative cyclization, deprotection, and dehydrogenation reactions. The use of MnO2 as a terminal oxidant for DDQ-mediated reactions is attractive based on economical and environmental factors.
• Kinetics‐Based Approach to Developing Electrocatalytic Variants of Slow Oxidations: Application to Hydride Abstraction‐Initiated Cyclization Reactions
  作者：Jean‐Marc I. A. Lawrence、Paul E. Floreancig

  DOI：10.1002/chem.202200335

  日期：2022.4.19

  through radical cation intermediates can be avoided by using constant potential conditions and current is maintained through the interplay between cation stability, oxidant strength, overpotential, and reaction concentration.

  通过原位电化学氧化剂再生，可以在无水条件下以亚化学计量的氧代铵离子负载生成氧代碳鎓和酰基亚胺鎓离子。通过使用恒定电位条件可以避免自由基阳离子中间体的分解，并通过阳离子稳定性、氧化剂强度、过电位和反应浓度之间的相互作用来维持电流。
• Enantioselective reduction of 2-substituted tetrahydropyran-4-ones using Daucus carota plant cells
  作者：J.S. Yadav、B.V. Subba Reddy、Ch. Sreelakshmi、G.G.K.S. Narayana Kumar、A. Bhaskar Rao

  DOI：10.1016/j.tetlet.2008.02.131

  日期：2008.4

  Enzymatic reduction of 2-substituted tetrahydropyran-4-ones with Daucus carota, plant cells as biocatalyst occurred in water under extremely mild and environmentally benign conditions giving a 1:1 mixture of diastereoselectively (2R,4S)- and (2S,4S)-2-aryl- or 2-alkyl-tetrahydropyranois in high yields. (c) 2008 Published by Elsevier Ltd.