2-hexyl-2,3-dihydro-4H-pyran-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-hexyl-2,3-dihydro-4H-pyran-4-one
• 英文别名: 2-Hexyl-2,3-dihydropyran-4-one
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: YTWHNMVNJSXDNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• 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

• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 仲辛酮 在 C₅₂H₇₂ClCrN₂O₂S₂ 、 三氟乙酸 作用下， 以 甲基叔丁基醚 、 二氯甲烷 为溶剂， 反应 64.5h， 以100%的产率得到2-hexyl-2,3-dihydro-4H-pyran-4-one
  参考文献：
  名称：

  用于多相不对称 Hetero-Diels-Alder 反应的基于铬-噻吩-salen 的聚合物

  摘要：

  已经合成了新的手性噻吩-salen 配体，并且相应的铬配合物被证明是促进不对称杂 Diels-Alder 反应的有效催化剂，具有良好的活性和高对映选择性（高达 88% ee）。这些配合物被成功地电聚合得到手性聚合物，作为不溶性粉末用于不对称多相催化。当进行连续的异-Diels-Alder 反应时，他们以高产率和对映选择性提供了预期的产物，在长达 15 次循环中没有效率损失。手性铬-salen-噻吩聚合物也成功地用于多底物程序，在该程序中，每次重复使用时都会引入结构不同的新醛，以提供纯形式的所需吡喃酮。(© Wiley-VCH Verlag GmbH & Co. KGaA,

  DOI：

  10.1002/ejoc.200701218

文献信息

• Asymmetric hetero Diels–Alder reaction using chiral cationic metallosalen complexes as catalysts
  作者：Kohsuke Aikawa、Ryo Irie、Tsutomu Katsuki

  DOI：10.1016/s0040-4020(00)01048-6

  日期：2001.1

  –chromium(III) complexes served as the catalysts for asymmetric hetero Diels–Alder reaction of Danishefsky's diene with aldehydes, achieving high enantioselectivity (up to 97% ee at 0°C). The reactions of aldehydes bearing no precoordinating functional group were well effected by using (R,R)-complexes as catalysts, while those of aldehydes bearing a precoordinating functionality were better effected by

  手性阳离子（R，S）-或（R，R）-（salen）–锰（III）和–铬（III）配合物用作Danishefsky's二烯与醛的不对称杂Diels–Alder反应的催化剂，实现了高对映选择性（0°C时ee高达97％）。通过使用（R，R）络合物作为催化剂，不带有预配位官能团的醛的反应效果良好，而通过使用（R，S）络合物，带有预配位官能团的醛的反应效果更好。
• Highly asymmetric hetero-Diels–Alder reaction using helical silica-supported Mn(III)-salen catalysts
  作者：Le Li、Yu Li、Di Pang、Fei Liu、Aqun Zheng、Guangbin Zhang、Yang Sun

  DOI：10.1016/j.tet.2015.08.045

  日期：2015.10

  Helical silica were prepared and functionalized by Mn(III)-salen complexes in order to catalyze asymmetric hetero-Diels Alder reactions. Characterizations revealed doping of sodium lactate facilitated porosity, hydrolysis resistance and chiral configuration of silica matrix. Catalysis revealed the combination of Mn(III)-salen with helical silica had excellent chiral induction. Major product configuration was affected by temperature and solvent. Loading imidazolium ionic liquid as solvent improved both enantioselectivity and catalyst recycling. (C) 2015 Elsevier Ltd. All rights reserved.
• Silica-based helical rod supporting guanosine compounds catalyzed asymmetric hetero-Diels–Alder reaction
  作者：Le Li、Guangbin Zhang、Benhua Huang、Lin Ren、Aqun Zheng、Junjie Zhang、Yang Sun

  DOI：10.1016/j.catcom.2015.01.016

  日期：2015.4

  A series of silica-based helical rods were prepared and functionalized for immobilization of guanosine compounds in catalytic asymmetric hetero-Diels-Alder reaction. Nitrogen physisorption, electron microscopy and amino acid adsorption revealed that helical rod has a hierarchical structure including morphology and internal channels, and doping of sodium lactate facilitates porosity and internal chirality of synthetic rods. Catalysis revealed that guanosine derivatives were catalytically active, combination of guanosine with L-sodium lactate-doped rod was more enantioselective than that with zero- or D-sodium lactate-doped samples, and recycling of supported Schiff-base-guanosine was stable during six cycles. (C) 2015 Elsevier B.V. All rights reserved.