3-benzyl-4,6-dimethyl-5-methoxycarbonyl-2H-pyran-2-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: 3-benzyl-4,6-dimethyl-5-methoxycarbonyl-2H-pyran-2-one
• 英文别名: Methyl 5-benzyl-2,4-dimethyl-6-oxopyran-3-carboxylate；methyl 5-benzyl-2,4-dimethyl-6-oxopyran-3-carboxylate
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: OIOVDYKSHYKYEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-benzyl-3-oxo-butyric acid methyl ester 、 2-丁炔酸甲酯 在 五羰基溴铼(I) 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以35%的产率得到3-benzyl-4,6-dimethyl-5-methoxycarbonyl-2H-pyran-2-one
  参考文献：
  名称：

  ReBr(CO)5-catalyzed sequential addition–cyclization of 1,3-dicarbonyl compounds with electron-deficient internal alkynes affording trisubstituted 2H-pyran-2-ones

  摘要：

  The reaction of 1,3-dicarbonyl compounds such as acetoacetate, acetylacetone, dibenzoylmethane, and benzoylacetate with electron-deficient internal alkynes in the presence of catalytic amount of ReBr( CO) 5 in toluene under neutral conditions resulted in the formation of 4,5,6-trisubstituted 2H-pyran-2-ones in moderate to high yield. The reaction took place via a two-step sequence including the rhenium(I)-catalyzed addition of the activated methylenes to alkynes to give enolic 2-alkenyl derivatives, and subsequently dealcoholic cyclization to form 2H-pyran-2-one derivatives. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.038

文献信息

• ReBr(CO)5-catalyzed sequential addition–cyclization of 1,3-dicarbonyl compounds with electron-deficient internal alkynes affording trisubstituted 2H-pyran-2-ones
  作者：Wen-Guo Zhao、Ruimao Hua

  DOI：10.1016/j.tet.2007.09.038

  日期：2007.11

  The reaction of 1,3-dicarbonyl compounds such as acetoacetate, acetylacetone, dibenzoylmethane, and benzoylacetate with electron-deficient internal alkynes in the presence of catalytic amount of ReBr( CO) 5 in toluene under neutral conditions resulted in the formation of 4,5,6-trisubstituted 2H-pyran-2-ones in moderate to high yield. The reaction took place via a two-step sequence including the rhenium(I)-catalyzed addition of the activated methylenes to alkynes to give enolic 2-alkenyl derivatives, and subsequently dealcoholic cyclization to form 2H-pyran-2-one derivatives. (c) 2007 Elsevier Ltd. All rights reserved.