6-(3-chlorophenyl)-4-isopropoxy-5,6-dihydro-2H-pyran-2-one | 1006691-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-(3-chlorophenyl)-4-isopropoxy-5,6-dihydro-2H-pyran-2-one
• 英文别名: 2-(3-Chlorophenyl)-4-propan-2-yloxy-2,3-dihydropyran-6-one
• CAS: 1006691-08-2
• 化学式: C₁₄H₁₅ClO₃
• 分子量: 266.724
• InChiKey: GVMKHNBYVAHWMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氯苯甲醛 、 异丙醇 、 isopropyl 2,3-butadienoate 在 三甲基膦 作用下， 以 氯仿 为溶剂， 生成 [(2S,6R)-2,6-Bis-(3-chloro-phenyl)-[1,3]dioxan-(4E)-ylidene]-acetic acid isopropyl ester 、 6-(3-chlorophenyl)-4-isopropoxy-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Alcohol-Assisted Phosphine Catalysis:  One-Step Syntheses of Dihydropyrones from Aldehydes and Allenoates

  摘要：

  This paper describes the phosphine-catalyzed annulation of methyl allenoate with various aromatic aldehydes to form 6-aryl-4-methoxy-5,6-dihydro-2-pyrones. In this reaction, the addition of an alcohol was necessary to induce dihydropyrone formation, with the optimal agent being methanol. Moreover, the addition of n-butyllithium suppressed the formation of the noncyclized product, leading to the exclusive isolation of the dihydropyrone. This method provides an efficient, one-step route toward disubstituted dihydropyrones from simple, stable starting materials.

  DOI：

  10.1021/ol702462w

文献信息

• Theory-guided design of Brønsted acid-assisted phosphine catalysis: synthesis of dihydropyrones from aldehydes and allenoates
  作者：Gardner S. Creech、Xue-Feng Zhu、Branden Fonovic、Travis Dudding、Ohyun Kwon

  DOI：10.1016/j.tet.2008.04.075

  日期：2008.7

  was also found for the first time to be a suitable catalyst for the synthesis of dihydropyrones. This method provides a one-step route toward functionalized dihydropyrones from simple, stable starting materials. In addition, new reaction pathways of phosphine-catalyzed allene annulations are unveiled, with the formation of dihydropyrones being the first example of dual activation in this sphere.

  膦催化的 2,3-丁二烯酸酯与醛的加成反应已扩展到双取代二氢-2-吡喃酮的形成。中间体两性离子β-鏻二烯醇盐向顺式中间体的必要平衡转变是通过使用布朗斯台德酸添加剂实现的，这破坏了顺式中间体中存在的有利库仑相互作用。通过一系列 DFT 计算分析了涉及布朗斯台德酸添加剂和膦参与形成 s-顺式 β-二烯酸鏻的协同相互作用的详细性质。与先前报道的醛与烯丙酸酯的环化不同，其中三烷基膦是最佳催化剂，在这项研究中，还首次发现三苯基膦是合成二氢吡喃酮的合适催化剂。该方法提供了一种从简单、稳定的起始材料制备功能化二氢吡喃酮的一步途径。此外，还揭示了膦催化丙二烯环化的新反应途径，其中二氢吡喃酮的形成是该领域双重活化的第一个例子。
• Alcohol-Assisted Phosphine Catalysis:  One-Step Syntheses of Dihydropyrones from Aldehydes and Allenoates
  作者：Gardner S. Creech、Ohyun Kwon

  DOI：10.1021/ol702462w

  日期：2008.2.1

  This paper describes the phosphine-catalyzed annulation of methyl allenoate with various aromatic aldehydes to form 6-aryl-4-methoxy-5,6-dihydro-2-pyrones. In this reaction, the addition of an alcohol was necessary to induce dihydropyrone formation, with the optimal agent being methanol. Moreover, the addition of n-butyllithium suppressed the formation of the noncyclized product, leading to the exclusive isolation of the dihydropyrone. This method provides an efficient, one-step route toward disubstituted dihydropyrones from simple, stable starting materials.