2-cyclohexyl-2,3-dihydropyran-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-cyclohexyl-2,3-dihydropyran-4-one
• 英文别名: 2-cyclohexyl-2,3-dihydro-4H-pyran-4-one；(R)-2-Cyclohexyl-2,3-dihydro4H-pyran4-one
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: PBLCYUZJPYQMKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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-cyclohexyl-2,3-dihydropyran-4-one 、 丙烯酸丁酯 在 氧气 、 palladium diacetate 、 溶剂黄146 、 对苯醌 作用下， 以 二甲基亚砜 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以69%的产率得到(E)-butyl 3-(2-cyclohexyl-4-oxo-3,4-dihydro-2H-pyran-5-yl)acrylate
  参考文献：
  名称：

  Palladium(ii)-catalyzed direct alkenylation of dihydropyranones

  摘要：

  开发了一种钯催化的直接烯丙基化反应，用于二氢吡喃酮。

  DOI：

  10.1039/c5ob00432b
• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 环己烷基甲醛 在 lithium methanolate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到2-cyclohexyl-2,3-dihydropyran-4-one
  参考文献：
  名称：

  A Lewis Base-catalyzed Hetero Diels–Alder Reaction between Aldehydes and the Danishefsky’s Diene

  摘要：

  报道了由甲醇锂催化的芳香醛和脂肪醛与1-甲氧基-3-三甲基硅氧基-1,3-丁二烯（Danishefsky双烯）的杂Diels-Alder反应。该反应通过Mukaiyama-Aldol反应途径进行，并以优异的产率获得了相应的2,3-二氢吡喃-4-酮骨架。

  DOI：

  10.1246/cl.2006.328

文献信息

• Cage-Shaped Borate Esters with Tris(2-oxyphenyl)methane or -silane System Frameworks Bearing Multiple Tuning Factors: Geometric and Substituent Effects on Their Lewis Acid Properties
  作者：Makoto Yasuda、Hideto Nakajima、Ryosuke Takeda、Sachiko Yoshioka、Satoshi Yamasaki、Kouji Chiba、Akio Baba

  DOI：10.1002/chem.201002789

  日期：2011.3.28

  Boron complexes that contain new tridentate ligands, tris(o‐oxyaryl)methanes and ‐silanes, were prepared. These complexes had a cage‐shaped structure around a boron center and showed higher Lewis acidity and catalytic activity than open‐shaped boron compounds. The cage‐shaped ligands determined the properties of the borates by altering the geometry and were consistently bound to the metal center by

  制备了含有新的三齿配体，三（邻-氧芳基）甲烷和-硅烷的硼配合物。这些络合物在硼中心周围具有笼状结构，并且比开放型硼化合物具有更高的路易斯酸度和催化活性。笼状配体通过改变几何形状决定了硼酸盐的性质，并通过螯合作用始终与金属中心结合。合成的化合物是L⋅B（OC 6 H 4）3 CH，L⋅B（OC 6 H 4）3 SiMe及其衍生物（L = THF或吡啶作为外部配体）。理论计算表明，笼形硼酸盐具有较大的二面角（C ipso-O-B-O）与开放形状的硼酸盐相比。由于二面角的几何作用，意味着与开口形相比，笼形硼酸盐具有更高的路易斯酸度。在笼形框架的芳基部分引入吸电子基团增加了路易斯酸度。用桥头硅代替桥头C会降低硼配合物的路易斯酸度，因为大的硅原子会降低C ipso -B-O的二面角。对氟取代的化合物B（OC 6 H 3 F）3 CH和邻苯基取代的化合物B（OC 6 H 3 Ph）3的配体交换率CH小于未取代的硼酸盐B（OC
• Recognition of Aromatic Compounds by π Pocket within a Cage-Shaped Borate Catalyst
  作者：Hideto Nakajima、Makoto Yasuda、Ryosuke Takeda、Akio Baba

  DOI：10.1002/anie.201200346

  日期：2012.4.16

  Taking shape: The ability of a Lewis acid catalyst to distinguish between aromatic and aliphatic hydrocarbon moieties was accomplished by using cage‐shaped borate catalysts B(OC6H3Aryl)3CH (see picture) having a π pocket derived from aryl substituents surrounding the boron center. The catalyst predominantly activated aromatic aldehydes over aliphatic ones for reaction.

  成形：路易斯酸催化剂区分芳族和脂族烃部分的能力是通过使用笼形硼酸盐催化剂B（OC 6 H 3 Aryl）3 CH（参见图片）实现的，该催化剂的π口袋衍生自周围的芳基取代基硼中心。相比于脂肪族醛，该催化剂主要活化了芳香族醛进行反应。
• Asymmetric cycloaddition reactions
  申请人：——

  公开号：US20020004602A1

  公开（公告）日：2002-01-10

  The present invention relates to a process for stereoselective cycloaddition reactions which generally comprises a cycloaddition reaction between a pair of substrates, each either chiral or prochiral, that contain reactive &pgr;-systems, in the presence of a non-racemic chiral catalyst, to produce a stereoisomerically enriched product. The present invention also relates to novel asymmetric catalyst complexes comprising a metal and an asymmetric tridentate ligand.

  本发明涉及一种立体选择性环加成反应的过程，通常包括在非外消旋手性催化剂的存在下，在含有反应性π-系统的手性或前手性的一对底物之间进行环加成反应，以产生立体异构体富集的产物。本发明还涉及一种新型的不对称催化剂配合物，包括金属和不对称三齿配体。
• Hetero Diels-Alder Type Reactions Between Danishefsky’s Dienes in the Presence of Lewis Base Catalysts. An Efficient Method for the Synthesis of Substituted 2,3-Dihydropyran-4-ones
  作者：Teruaki Mukaiyama、Takayuki Kitazawa

  DOI：10.3987/com-06-s(o)52

  日期：——
• Methods of performing cycloadditions, reaction mixtures, and methods of performing asymmetric catalytic reactions
  申请人：Rawal Viresh H.

  公开号：US20100184999A1

  公开（公告）日：2010-07-22

  Methods of performing cycloadditions are described that include (a) combining a first reactant and a second reactant in a hydrogen bonding solvent to form a reaction mixture; and (b) reacting the first reactant and the second reactant to form a cycloadduct. Methods of performing asymmetric catalytic reactions are also described that include (a) combining a first reactant, a second reactant, and a catalytic amount of a chiral hydrogen-bond donor in a solvent to form a reaction mixture; and (b) reacting the first reactant and the second reactant to form an enantiomeric excess of a reaction product. Reaction mixtures corresponding to these methods are also described.