(S)-5-acetyl-4-(4-chlorophenyl)-6-methyl-3,4-dihydro-2H-pyran-2-one | 1352755-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (S)-5-acetyl-4-(4-chlorophenyl)-6-methyl-3,4-dihydro-2H-pyran-2-one
• 英文别名: (4S)-5-acetyl-4-(4-chlorophenyl)-6-methyl-3,4-dihydropyran-2-one
• CAS: 1352755-83-9
• 化学式: C₁₄H₁₃ClO₃
• 分子量: 264.708
• InChiKey: HRKVANGEVJZWGG-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2E)-3-(4-氯苯基)丙烯酰氯 在 C₂₇H₃₁N₂O₂⁽¹⁺⁾*Br^(1-) 、 potassium carbonate 、 三乙胺 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (R)-5-acetyl-4-(4-chlorophenyl)-6-methyl-3,4-dihydro-2H-pyran-2-one 、 (S)-5-acetyl-4-(4-chlorophenyl)-6-methyl-3,4-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of 3,4-Dihydropyran-2-ones via Phase-Transfer-Catalyzed Addition–Cyclization of Acetylacetone to Cinnamic Thioesters

  摘要：

  Herein, we present the first example of synthesis of 3,4-dihydropyran-2-ones from cinnamic thioesters via a stereoselective phase-transfer-catalyzed domino Michael-cyclization reaction with acetylacetone. The reaction proceeded under the catalysis of Cinchona-derived quaternary ammonium phenoxide that, in combination with inorganic bases, provided 3,4-dihydropyran-2-ones in yields of up to 93% and enantioselectivities of up to 88% enantiomeric excess.

  DOI：

  10.1021/acs.joc.9b03216

文献信息

• N-Heterocyclic Carbene-Catalyzed Enantioselective Annulation of Bromoenal and 1,3-Dicarbonyl Compounds
  作者：Fang-Gang Sun、Li-Hui Sun、Song Ye

  DOI：10.1002/adsc.201100622

  日期：2011.11

  Highly enantioselective [3+3] annulation reactions of bromoenals and 1,3-dicarbonyl compounds are reported. In addition, both enantiomers of the resultant dihydropyranone could be easily obtained by choosing N-heterocyclic carbenes (NHCs) with the same stereocenter but different substituents under the optimized reaction conditions.

  报道了溴烯和1，3-二羰基化合物的高度对映选择性[3 + 3]环化反应。另外，通过在优化的反应条件下选择具有相同立体中心但具有不同取代基的N-杂环卡宾（NHC），可以轻松获得所得二氢吡喃酮的两种对映体。
• Asymmetric aerobic oxidative NHC-catalysed synthesis of dihydropyranones utilising a system of electron transfer mediators
  作者：A. Axelsson、E. Hammarvid、L. Ta、H. Sundén

  DOI：10.1039/c6cc06060a

  日期：——

  Enantioselective synthesis of dihydropyranones via aerobic multistep electron transfer NHC catalysis. Selective introduction of O2 as the terminal oxidant.

  通过好氧多步电子转移NHC催化对映选择性合成二氢吡喃酮。选择性引入O 2作为末端氧化剂。
• Enantioselective N-Heterocyclic Carbene-Catalyzed Annulations of 2-Bromoenals with 1,3-Dicarbonyl Compounds and Enamines<i>via</i>Chiral α,β-Unsaturated Acylazoliums
  作者：Santhivardhana Reddy Yetra、Anup Bhunia、Atanu Patra、Manoj V. Mane、Kumar Vanka、Akkattu T. Biju

  DOI：10.1002/adsc.201300219

  日期：2013.4.15

  The N‐heterocyclic carbene (NHC)‐catalyzed generation of chiral α,β‐unsaturated acylazoliums from 2‐bromoenals followed by their interception with 1,3‐dicarbonyl compounds or enamines, the formal [3+3] annulation reaction, is reported. The reaction results in the enantioselective synthesis of synthetically and medicinally important dihydropyranones and dihydropyridinones, and tolerates a wide range

  据报道，N-杂环卡宾（NHC）催化了从2-溴烯醛中生成手性α，β-不饱和酰基la，然后被1,3-二羰基化合物或烯胺截获，这是正式的[3 + 3]环化反应。该反应导致合成上和医学上重要的二氢吡喃酮和二氢吡啶并酮的对映选择性合成，并具有宽泛的官能团。值得注意的是，该反应在温和的反应条件下利用相对较低的催化剂负载量进行。此外，基于DFT计算，提出了一种机制方案，涉及亲核试剂从α，β-不饱和酰基环的平面下方攻击，以及对映体诱导的模式。
• Enantioselective <i>N</i>-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants
  作者：Jing Cao、Rachel Gillard、Azar Jahanbakhsh、Martin Breugst、David W. Lupton

  DOI：10.1021/acscatal.0c02705

  日期：2020.10.16

  An approach to the α,β-unsaturated acyl azolium has been developed that exploits N-heterocyclic carbenes (NHCs) and acyl fluorides, without additional oxidants, bases, or preactivated pro-nucleophiles. These conditions have been applied in four classes of NHC-catalyzed reaction. In all cases, the expected products were produced with high yield and enantioselectivity, using two sets of closely related

  已经开发出一种α，β-不饱和酰基偶氮的方法，该方法利用了N-杂环卡宾（NHC）和酰基氟，而无需使用其他氧化剂，碱或预活化的亲核试剂。这些条件已应用于四类NHC催化的反应中。在所有情况下，使用两组紧密相关的反应条件无需额外优化即可生产出预期的产物，具有高收率和对映选择性。