3-benzyl-2,3-dihydro-4-pyranone | 135695-92-0

• 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-2,3-dihydro-4-pyranone
• 英文别名: 3-Benzyl-2H-pyran-4(3H)-one；3-benzyl-2,3-dihydropyran-4-one
• CAS: 135695-92-0
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: JBMCBJCKVXBGLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-2,3-dihydro-4-pyranone 在 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 3-Benzyl-4-methyl-2,3-dihydropyran-6-one
  参考文献：
  名称：

  二氢-α-吡喃酮到二氢-α-吡喃酮的烷基羰基转座

  摘要：

  二氢α吡喃酮（2）由β羟基酮（制备1）。二氢吡喃酮（2）通过烷基化的1，3-羰基转座转化为不饱和δ-内酯（4）。

  DOI：

  10.1016/s0040-4039(00)77655-6
• 作为产物：
  描述：

  2-苄基-1-羟基-3-丁酮 、 原甲酸三乙酯 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到3-benzyl-2,3-dihydro-4-pyranone
  参考文献：
  名称：

  二氢-α-吡喃酮到二氢-α-吡喃酮的烷基羰基转座

  摘要：

  二氢α吡喃酮（2）由β羟基酮（制备1）。二氢吡喃酮（2）通过烷基化的1，3-羰基转座转化为不饱和δ-内酯（4）。

  DOI：

  10.1016/s0040-4039(00)77655-6

文献信息

• Chemistry of dioxenium cations. Synthetic and mechanistic studies on the stereocontrolled formation of tetrahydropyrans from homoallylic alcohols and ortho esters
  作者：Francoise Perron-Sierra、Michele A. Promo、Van A. Martin、Kim F. Albizati

  DOI：10.1021/jo00021a043

  日期：1991.10

  Despite their long history, dioxenium cations are underutilized reactive synthetic intermediates. It was found that ortho esters and homoallylic alcohols in the presence of Lewis acids provide 4-heterosubstituted pyranosides in a stereoselective manner. The mechanistic course of events was supported by control experiments and synthesis of a putative mixed ortho ester intermediate which exhibited identical reactivity. A transition state for termination of the dioxenium cation-olefin cyclization is proposed, involving intramolecular delivery of chloride by a coordinated tin species. Structure-reactivity relationships indicate that a cation-stabilizing substituent (alkyl or alkoxy) at the internal position of the olefin is required for cyclization. A variety of 3-alkyl-substituted homoallylic alcohols cyclize cleanly to substituted 2-alkoxytetrahydropyrans in good yield. beta-silyloxy silyl enol ethers were found to smoothly provide 4-oxotetrahydropyranosides when subjected to the same reaction conditions. For these substrates, the course of the cyclization proceeds in a different manner involving a rapid intermolecular Mukaiyama aldol condensation followed by transacetalization.
• Alkylative carbonyl transposition of dihydro-α-pyrones to dihydro-α-pyrones
  作者：A. Nangia、P.Bheema Rao

  DOI：10.1016/s0040-4039(00)77655-6

  日期：1993.4

  Dihydro-α-pyrones (2) are prepared from β-hydroxy ketones (1). Dihydropyrones (2) are transformed to unsaturated δ-lactones (4) via an alkylative 1,3-carbonyl transposition.

  二氢α吡喃酮（2）由β羟基酮（制备1）。二氢吡喃酮（2）通过烷基化的1，3-羰基转座转化为不饱和δ-内酯（4）。