2,3-二氢-6-甲基-4H-吡喃-4-酮 | 22697-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2,3-二氢-6-甲基-4H-吡喃-4-酮
• 英文名称: 2-methyl-5,6-dihydro-4-pyrone
• 英文别名: 6-methyl-2H-pyran-4(3H)-one；6-methyl-2,3-dihydro-pyran-4-one；6-methyl-2,3-dihydropyran-4-one
• CAS: 22697-33-2
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: OXQAUABVOFKUNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2,3-二氢-6-甲基-4H-吡喃-4-酮 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 丙酮 、 乙腈 为溶剂， 反应 7.33h， 生成 3α-tert-butyl-14,14-dicarbethoxy-6β,7β-dihydro-2,4,11-trioxa-5,8-dioxo-13β,15β-tetracyclo[4.9.0.0^1,12.0^7,12]pentadecane
  参考文献：
  名称：

  Enantioselective Synthesis of Spiro Ethers and Spiro Ketals via Photoaddition of Dihydro-4-pyrones to Chiral 1,3-Dioxin-4-ones

  摘要：

  A versatile and highly stereoselective synthesis of spiro ethers and spiro ketals is presented. The key step in the developed synthetic sequence is based on diastereoselective intramolecular photoaddition of dihydro-4-pyrones to chiral 1,3-dioxin-4-ones. Subsequent fragmentation of the produced four-membered ring provides spiro ether structures. The spiro ethers can be transformed to their corresponding spiro ketals, with retention of configuration at the spiro center, via Baeyer-Villager oxidation. The configuration of the spiro center is defined by the facial selectivity at the photocycloaddition step. Two examples of complete stereofacial selectivity were achieved. The unique and important application of the developed sequence was demonstrated in enantioselective synthesis of a less thermodynamically stable spiro ketal 43.

  DOI：

  10.1021/jo970816r
• 作为产物：
  描述：

  4-hydroxy-1-(2-methyl-1,3-dioxolan-2-yl)butan-2-one 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到2,3-二氢-6-甲基-4H-吡喃-4-酮
  参考文献：
  名称：

  A convenient route to 2,6-dialkyl-2,3-dihydro-4H-pyran-4-ones via oxidative cleavage of protected 1-(2-oxoalkyl)-cyclopropanols. Synthesis of (±)-hepialone and its natural congener

  摘要：

  An efficient strategy for the synthesis of 2,6-dialkyl-2,3-dihydro-4H-pyran-4-ones has been developed, the key steps of which are oxidative cleavage of the three-membered rings of 1-(2-oxoalkyl)-cyclopropanols and acid-promoted cyclization of the resulting beta-hydroxyketones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.042

文献信息

• Palladium-Catalyzed Asymmetric Quaternary Stereocenter Formation
  作者：Aditya L. Gottumukkala、Kiran Matcha、Martin Lutz、Johannes G. de Vries、Adriaan J. Minnaard

  DOI：10.1002/chem.201200694

  日期：2012.5.29

  An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β‐disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (−)‐α‐cuparenone

  通过将芳基硼酸共轭加成到各种β，β-二取代的碳环，杂环和无环烯酮上，提出了一种有效的钯催化剂，用于形成苄基季立体中心。该催化剂易于由PdCl 2，PhBOX和AgSbF 6制备，并以高达99％的对映体过量提供产物。基于此策略，仅需两个步骤即可制备（-）-α-cuparenone。
• Non-linear optically active molecules, their synthesis, and use
  申请人：McGinniss D. Vincent

  公开号：US20080004415A1

  公开（公告）日：2008-01-03

  In one aspect, the present invention provides a hyperpolarizable organic chromophore. The chromophore is a nonlinear optically active compound that includes a π-donor conjugated to a π-acceptor through a π-electron conjugated bridge. In other aspects of the invention, donor structures and acceptor structures are provided. In another aspect of the invention, a chromophore-containing polymer is provided. In one embodiment, the chromophore is physically incorporated into the polymer to provide a composite. In another embodiment, the chromophore is covalently bonded to the polymer, either as a side chain polymer or through crosslinking into the polymer. In other aspects, the present invention also provides a method for making the chromophore, a method for making the chromophore-containing polymer, and methods for using the chromophore and chromophore-containing polymer.

  在一个方面，本发明提供了一种高极化有机色团。该色团是一种非线性光学活性化合物，包括一个π-给体通过一个π-电子共轭桥连接到一个π-受体上。在本发明的其他方面，提供了给体结构和受体结构。在发明的另一个方面，提供了含有色团的聚合物。在一种实施例中，色团被物理地并入聚合物中以提供复合材料。在另一种实施例中，色团通过侧链聚合物或交联到聚合物中与聚合物共价键合。在其他方面，本发明还提供了制备色团的方法、制备含有色团的聚合物的方法以及使用色团和含有色团的聚合物的方法。
• Hydration of allenylacetylenic alcohols ? New route to 6-methyl-2,3-dihydro-4-pyranones
  作者：A. P. Khrimyan、A. V. Karapetyan、Sh. O. Badanyan

  DOI：10.1007/bf00514299

  日期：1984.5
• Melikyan, G. G.; Tosunyan, A. A.; Babayan, E. V., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 10, p. 1802 - 1807
  作者：Melikyan, G. G.、Tosunyan, A. A.、Babayan, E. V.、Atanesyan, K. A.、Badanyan, Sh. O.

  DOI：——

  日期：——
• DESHAYES C.; GELIN S., J. HETEROCYCL. CHEM., 1979, 16, NO 4, 657-660
  作者：DESHAYES C.、 GELIN S.

  DOI：——

  日期：——

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