2-萘-1-基-2,3-二氢吡喃-4-酮 | 871918-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-萘-1-基-2,3-二氢吡喃-4-酮
• 英文名称: 2-(1-naphthyl)-2,3-dihydro-4H-pyran-4-one
• 英文别名: 2-naphthalen-1-yl-2,3-dihydropyran-4-one；2-(naphthalen-1-yl)-2,3-dihydro-4H-pyran-4-one
• CAS: 871918-59-1
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: VSSCOMPJVNFZIE-UHFFFAOYSA-N

物化性质

• 沸点：
  395.7±37.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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-萘-1-基-2,3-二氢吡喃-4-酮 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 生成 2-(naphthalen-1-yl)-3,4-dihydro-2H-pyran-4-ol
  参考文献：
  名称：

  通过钯催化的脱羧烯丙基化可轻松获得顺式2,6-二取代的四氢吡喃：（±）-环草碱和（+）-去细胞肽A和B的总合成

  摘要：

  顺式-2,6-四氢吡喃是生物活性天然产物的重要结构骨架。顺式-2,6-二取代-3,6-二氢吡喃前体作为顺式-2,6-四氢吡喃前体的简便合成方法具有很高的区域选择性和立体选择性，且收率很高。该反应涉及各种3,4-dihydro-2 H-吡喃底物的钯催化脱羧烯丙基化。将此反应扩展至1,2-不饱和碳水化合物可实现具有挑战性的β-C-糖基化。基于此方法，只需简单的步骤即可完成（±）-中心叶lob碱和（+）-去细胞肽A和B的总合成。

  DOI：

  10.1002/chem.201303328
• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 1-萘甲醛 在 C₆₅H₄₅BO₄ 作用下， 以 二氯甲烷 为溶剂， 反应 45.0h， 以98%的产率得到2-萘-1-基-2,3-二氢吡喃-4-酮
  参考文献：
  名称：

  笼形C3对称硼路易斯酸，用于手性分子识别和不对称催化

  摘要：

  手性路易斯酸在各种类型的手性分子的精确构建中起着重要作用。在这里，设计并合成了笼形硼酸盐2，它是一种手性路易斯酸，具有独特的C 3对称结构，该结构由三个同手性双萘基部分组成。X射线晶体学分析清楚地阐明了具有手性的2的高度对称结构。2 THF独特的手性环境表现出一些简单的胺和亚砜的手性识别。而且，应用2⋅THF作为手性路易斯酸催化剂的杂Diels-Alder反应提供了对映体选择性产物，该产物是根据对光收率和反应温度之间关系的分析，通过熵控制途径获得的。尤其是，尽管要求高温，但2 THFTHF的强大手性反应场还是第一个使用简单的二烯进行不对称杂Diels-Alder反应的例子。

  DOI：

  10.1002/chem.201605712

文献信息

• A Lewis Base-catalyzed Hetero Diels–Alder Reaction between Aldehydes and the Danishefsky’s Diene
  作者：Teruaki Mukaiyama、Takayuki Kitazawa、Hidehiko Fujisawa

  DOI：10.1246/cl.2006.328

  日期：2006.3

  A lithium methoxide-catalyzed hetero Diels–Alder reaction of aromatic and aliphatic aldehydes with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (Danishefsky’s diene) is described. It proceeds through the Mukaiyama-Aldol reaction pathway and affords the corresponding 2,3-dihydropyran-4-one skeletons in good to excellent yields.

  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。
• Axially Chiral Biaryl Diols Catalyze Highly Enantioselective Hetero-Diels−Alder Reactions through Hydrogen Bonding
  作者：Aditya K. Unni、Norito Takenaka、Hisashi Yamamoto、Viresh H. Rawal

  DOI：10.1021/ja044076x

  日期：2005.2.1

  Axially chiral 1,1'-biaryl-2,2'-dimethanol (3, BAMOL) family of diols are highly effective catalysts for enantioselective hetero-Diels-Alder reactions between aminosiloxydiene 1 and a wide variety of unactivated aldehydes. The reactions proceed in useful yields and excellent enantioselectivities. The diols function in the same capacity as Lewis acids, by activating the aldehyde carbonyl group through

  轴向手性 1,1'-联芳基-2,2'-二甲醇 (3, BAMOL) 二醇家族是氨基甲硅烷氧基二烯 1 和多种未活化醛之间的对映选择性杂 Diels-Alder 反应的高效催化剂。反应以有用的产率和优异的对映选择性进行。二醇的功能与路易斯酸相同，通过氢键活化醛羰基。
• 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.
• Dramatically Synergetic Effect of Carboxylic Acid Additive on Tridentate Titanium Catalyzed Enantioselective Hetero-Diels–Alder Reaction: Additive Acceleration and Nonlinear Effect
  作者：Yu Yuan、Jiang Long、Jie Sun、Kuiling Ding

  DOI：10.1002/1521-3765(20021104)8:21<5033::aid-chem5033>3.0.co;2-t

  日期：2002.11.4

  This paper describes the successful development of a group of highly, efficient chiral tridentate titanium catalysts for hetero-Diels - Alder reaction of Danishefsky's diene and a variety of aldehydes through ligand and additive diversity. Dramatically synergetic effect of carboxylic acid additives and influence of substituent in chiral Schiff base ligands on the enantioselectivities of the reaction are reported. It was found that a chiral drug Naproxen (A21) was a highly efficient additive for Ti-catalyzed HDA reaction, affording 2-substituted 2,3-dihydro-4H-pyran-4-one in up to 97% ee and > 99% yields. Quantitative study of the effect of chiral carboxylic acid A21 revealed that the reaction could be accelerated by one order of magnitude. Another interesting feature of present catalytic system is the existence of significant positive nonlinear effect. which indicates that the heterochiral Schiff base-titanium complexes may have higher stability than their homochiral counterparts. As a result. the homochiral Schiff base - titanium complexes with higher ee than that of starting ligand will react with carboxylic acid additive to form the more active species and predominate the catalytic process. The isolation and characterization of stable heterochiral ((+/-)-L1)(2)Ti complex has also been successful, which strongly supported the explanation for positive nonlinear effect observed in the catalytic system.
• 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：——