3-(tetrahydro-2H-pyran-2-yl)pentane-2,4-dione | 55277-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(tetrahydro-2H-pyran-2-yl)pentane-2,4-dione
• 英文别名: 3-(Oxan-2-yl)pentane-2,4-dione
• CAS: 55277-12-8
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: YTROHNXITOGKKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(tetrahydro-2H-pyran-2-yl)pentane-2,4-dione 在 镍 氢氧化钾 、 氢气 作用下， 生成 3-(5-hydroxy-pentyl)-pentane-2,4-dione
  参考文献：
  名称：

  Lagrenee,M.; Glacet,C., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1974, vol. 279, p. 1157 - 1158

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲氧基四氢吡喃 、 乙酰丙酮 在 indium(III) chloride 作用下， 反应 60.0h， 以90%的产率得到3-(tetrahydro-2H-pyran-2-yl)pentane-2,4-dione
  参考文献：
  名称：

  Addition of carbon nucleophiles to cyclic N-acyliminium and oxocarbenium ions under solvent-free conditions

  摘要：

  The InCl3-catalyzed addition of carbon nucleophiles to cyclic N-acyliminium and oxocarbenium ions under solvent-free conditions at room temperature is described. The corresponding-substituted heterocycles were obtained in moderate to excellent yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.023

文献信息

• The Lewis Acidic Ruthenium-Complex-Catalyzed Addition of β-Diketones to Alcohols and Styrenes Is in Fact Brønsted Acid Catalyzed
  作者：Pei Nian Liu、Zhong Yuan Zhou、Chak Po Lau

  DOI：10.1002/chem.200700705

  日期：2007.10.15

  toward 1-phenylethanol in the presence of HClO4; it also fails to catalyze the addition of acetylacetone to 1-phenylethanol. On the basis of these observations, it is proposed and confirmed by independent experiments that the catalytic addition of beta-diketones to the secondary alcohols is in fact catalyzed by the Bronsted acid HClO4, which is generated by the reaction of cis-[Ru(6,6'-Cl2bipy)2(H2O)2](ClO4)2

  联吡啶-钌络合物顺式[[Ru（6,6'-Cl2bipy）2（H2O）2] 2+]的高氯酸盐可有效催化将β-二酮添加到仲醇和苯乙烯中，从而生成α-烷基化的β-二酮。在乙酰丙酮与1-苯乙醇的催化加成反应中，催化后分离出κ2-乙酰丙酮络合物[Ru（6,6'-Cl2bipy）2（κ2-acac）] ClO4。通过使顺式-[Ru（6,6'-Cl2bipy）2（H2O）2]（ClO4）2与乙酰丙酮反应，可以轻松合成该配合物。[Ru（6,6'-Cl2bipy）2（kappa2-acac）] ClO4在HClO4存在下对1-苯基乙醇不反应；它也不能催化将乙酰丙酮加到1-苯基乙醇中。根据这些观察，
• Efficient and recyclable solid acid-catalyzed alkylation of active methylene compound via oxonium intermediate for atom economical synthesis of organic compounds
  作者：Dhanaji R. Naikwadi、Balasaheb D. Bankar、Krishnan Ravi、Ankush V. Biradar

  DOI：10.1007/s11164-021-04499-3

  日期：2021.9

  enol ethers and aryl acetals through oxonium intermediate under solvent-free conditions using heterogeneous solid acid catalysts. Among studied solid acid catalysts, Amberlyst-15 gave excellent yields (35–85%) of alkylated products. The catalyst showed broader substrate scope, and a recyclable catalytic cost-efficient approach of the alkylation was examined on the different types of cyclic enol ethers

  在目前的工作中，我们报告了活性亚甲基化合物与环烯醇醚和芳基缩醛在无溶剂条件下使用多相固体酸催化剂通过氧鎓中间体的催化反应。在研究的固体酸催化剂中，Amberlyst-15 的烷基化产物产率极好（35-85%）。该催化剂显示出更广泛的底物范围，并且在不同类型的环烯醇醚和芳基缩醛上研究了一种可回收的、具有成本效益的烷基化催化方法。
• Design, diversity-oriented synthesis and structure activity relationship studies of quinolinyl heterocycles as antimycobacterial agents
  作者：Venkatesham Rachakonda、Manjula Alla、Sudha Sravanti Kotipalli、Ramesh Ummani

  DOI：10.1016/j.ejmech.2013.10.034

  日期：2013.12

  heterocyclic frameworks thus obtained were evaluated for their antimycobacterial activity. The active scaffolds were further explored by a parallel library generation in order to establish SAR. Further, low cytotoxicity against A549 cell line enhances the potential of the synthesized molecules as promising antimycobacterial agents.

  当前的研究报道了以共同的2-甲基，C-4未取代的喹啉部分为中心关键杂环的新型双杂环的设计和面向多样性的合成。采用基于试剂的骨骼多样性方法；已经完成了在喹啉部分的C-3位具有不同杂环的双杂环的简便合成。评价由此获得的广泛范围的杂环框架的抗分枝杆菌活性。通过建立平行文库进一步研究活性支架以建立SAR。此外，针对A549细胞系的低细胞毒性增强了合成分子作为有前景的抗分枝杆菌剂的潜力。
• FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins
  作者：Christophe Dal Zotto、Julien Michaux、Araceli Zarate-Ruiz、Eric Gayon、David Virieux、Jean-Marc Campagne、Vincent Terrasson、Grégory Pieters、Anne Gaucher、Damien Prim

  DOI：10.1016/j.jorganchem.2010.09.031

  日期：2011.1

  A direct intermolecular addition of nitrogen and 1,3-dicarbonyl nucleophiles to stabilized double bonds (styrenes, 1,3-dienes, enol-ethers, sugars..) in the presence of green and inexpensive FeCl3 catalyst is described. (C) 2010 Elsevier B.V. All rights reserved.
• Oxonium ions in organic synthesis: condensation of 2,3-dihydrofuran and 3,4-dihydro-2H-pyran with 1,3-dicarbonyl compounds
  作者：Ron Bihovsky、Mudubagilu Udaya Kumar、Shuji Ding、Arun Goyal

  DOI：10.1021/jo00279a012

  日期：1989.9