(+)-(S)-2,3-二氢-2-(2-甲氧基苯基)-4H-吡喃-4-酮 | 333749-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (+)-(S)-2,3-二氢-2-(2-甲氧基苯基)-4H-吡喃-4-酮
• 英文名称: 2-(2-methoxyphenyl)-2,3-dihydro-4H-pyran-4-one
• 英文别名: (2S)-2-(2-Methoxyphenyl)-2,3-dihydro-4H-pyran-4-one；(2S)-2-(2-methoxyphenyl)-2,3-dihydropyran-4-one
• CAS: 333749-07-8
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: USXRDWKUDRMMPX-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  甲醇 、 (+)-(S)-2,3-二氢-2-(2-甲氧基苯基)-4H-吡喃-4-酮 在 三甲基氯硅烷 作用下， 反应 2.0h， 生成 (R)-2,4,4-trimethoxy-6-(o-methoxyphenyl)tetrahydropyran 、 (S)-2,4,4-trimethoxy-6-(o-methoxyphenyl)tetrahydropyran
  参考文献：
  名称：

  Mihara, Jun; Aikawa, Kohsuke; Uchida, Tatsuya, Heterocycles, 2001, vol. 54, # 1, p. 395 - 404

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 air 作用下， 以 二氯甲烷 为溶剂， 生成 (+)-(S)-2,3-二氢-2-(2-甲氧基苯基)-4H-吡喃-4-酮
  参考文献：
  名称：

  Stereoselective hetero Diels–Alder reactions of chiral tricarbonyl (η6-benzaldehyde)chromium complexes

  摘要：

  The ZnCl2-promoted cycloaddition of a series of enantiopure ortho-substituted benzaldehyde-Cr(CO), complexes and Danishefsky's diene gave the corresponding 2-aryl pyranones in good yields and complete enantio specificity. Some of the mechanistic aspects of the cycloaddition were investigated and the reaction extended to different dienes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00347-0

文献信息

• Chiral Chromium Salen@rGO as Multipurpose and Recyclable Heterogeneous Catalyst
  作者：Mariam Abd El Sater、Mohamed Mellah、Diana Dragoe、Emilie Kolodziej、Nada Jaber、Emmanuelle Schulz

  DOI：10.1002/chem.202101003

  日期：2021.6.25

  to promote asymmetric catalysis in repeated cycles, without loss of activity or enantioselectivity. This specific behavior was demonstrated in two different catalytic reactions (up to ten reuses) promoted by chromium salen complexes, the cyclohexene oxide ring-opening reaction and the hetero-Diels-Alder cycloaddition between various aldehydes and Danishefsky's diene. Furthermore, the chiral chromium

  描述了通过 π-π 非共价相互作用在还原氧化石墨烯 (rGO) 上首次固定芘标记的铬萨伦复合物。获得了非常强大的负载催化系统，以促进重复循环中的不对称催化，而不会损失活性或对映选择性。这种特殊行为在由铬盐络合物促进的两种不同催化反应（最多十次重复使用）中得到证明，即氧化环己烯开环反应和各种醛与丹麦谢夫斯基二烯之间的杂-Diels-Alder 环加成反应。此外，已发现手性铬 salen@rGO 与多底物类型的使用兼容，其中每次重复使用催化剂时都会修改所涉及的底物结构。
• A Highly Enantioselective Hetero-Diels−Alder Reaction of Aldehydes with Danishefsky's Diene Catalyzed by Chiral Titanium(IV) 5,5‘,6,6‘,7,7‘,8,8‘-Octahydro-1,1‘-bi-2-naphthol Complexes
  作者：Bin Wang、Xiaoming Feng、Yaozong Huang、Hui Liu、Xin Cui、Yaozhong Jiang

  DOI：10.1021/jo016240u

  日期：2002.4.1

  products with very high enantioselectivity (up to 99% ee) and yield (92%). The hetero-Diels-Alder reaction of other aldehydes with 1 under the catalysis of TiHBOL is a general reaction which proceeds well with very high enantioselectivity and isolated yield for various aldehydes at 0 degrees C to room temperature. Based on the experimental results, the proposed mechanism of the hetero-Diels-Alder reaction

  研究了手性路易斯酸对醛与Danishefsky's diene（1）之间的杂Diels-Alder反应的催化作用。作为苯甲醛和1之间杂Diels-Alder反应的催化剂，已研究了各种不同配体和路易斯酸的组合，并发现容易获得的Ti（IV）-H（8）-BINOL（TiHBOL配合物是反应的非常有效的催化剂，导致产物具有很高的对映选择性（高达99％ee）和产率（92％）。在TiHBOL催化下，其他醛与1的杂Diels-Alder反应是一种常规反应，在0℃至室温下，该反应进行得很好，具有很高的对映选择性并分离出各种醛。根据实验结果，
• Highly efficient enantioselective synthesis of optically active dihydropyrones by chiral titanium(iv) (5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-bi-2-naphthol) complexes
  作者：Bin Wang、Xiaoming Feng、Xin Cui、Hui Liu、Yaozhong Jiang

  DOI：10.1039/b004813p

  日期：——

  The asymmetric hetero-Diels–Alder reaction of Danishefsky’s diene and an aldehyde catalyzed by 20 mol% chiral H8-BINOL–Ti(IV) affords the corresponding 2-substitutent-2,3-dihydro-4H-pyran-4-one with ees of up to 99% under mild reaction conditions.

  由 20 mol% 手性 H8-BINOL-Ti(IV) 催化的 Danishefsky 的二烯和醛的不对称杂 Diels-Alder 反应得到相应的 2-substitutent-2,3-dihydro-4H-pyran-4-one 和 ees在温和的反应条件下高达 99%。
• Highly Active 3-Oxobutylideneaminatocobalt Complex Catalysts for an Enantioselective Hetero Diels–Alder Reaction
  作者：Satoko Kezuka、Tsuyoshi Mita、Natsuki Ohtsuki、Taketo Ikeno、Tohru Yamada

  DOI：10.1246/bcsj.74.1333

  日期：2001.7

  Optically active 3-oxobutylideneaminatocobalt(III) complexes were developed as effective catalysts for the enantioselective hetero Diels–Alder reaction of aromatic and aliphatic aldehydes with 3-(t-butyldimethylsilyloxy)-1-methoxy-1,3-butadiene. In the presence of the highly active cationic cobalt(III) complex, the hetero Diels–Alder reactions proceeded to afford the corresponding dihydropyran-4-ones

  光学活性 3-氧代丁叉氨基钴 (III) 配合物被开发为芳香族和脂肪族醛与 3-(叔丁基二甲基甲硅烷氧基)-1-甲氧基-1,3-丁二烯的对映选择性杂 Diels-Alder 反应的有效催化剂。在高活性阳离子钴 (III) 配合物的存在下，杂 Diels-Alder 反应进行以提供相应的具有高性能和高对映选择性的二氢吡喃-4-酮。与邻位配位基团取代的芳香醛反应进行得更顺利。
• Discovery of Exceptionally Efficient Catalysts for Solvent-Free Enantioselective Hetero-Diels−Alder Reaction
  作者：Jiang Long、Jieyu Hu、Xiaoqiang Shen、Baoming Ji、Kuiling Ding

  DOI：10.1021/ja0172518

  日期：2002.1.1

  Combinatorial coordination chemistry strategy combined with high-throughput screening techniques has been successfully applied to engineering practical enantioselective catalysts for asymmetric hetero-Diels-Alder reaction. The reaction of Danishefsky's diene with a variety of aldehydes can be carried out with 0.1-0.005 mol % of H4-BINOL/Ti/H4-BINOL or H4-BINOL/Ti/H8-BINOL catalysts at room temperature under solvent- and MS-free conditions to afford dihydropyrone derivatives with up to quantitative yield and 99.8% ee.