1-(2-hydroxyphenyl)-3,3-dimethoxy-1-propanone | 127841-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-hydroxyphenyl)-3,3-dimethoxy-1-propanone
• 英文别名: 1-(2-Hydroxyphenyl)-3,3-dimethoxypropan-1-one
• CAS: 127841-40-1
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: AZJHDAMEFHUARL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2'-羟基苯乙酮 在 四氯化锡 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 1-(2-hydroxyphenyl)-3,3-dimethoxy-1-propanone
  参考文献：
  名称：

  Chemistry of aldolate dianions. β-Silyloxy silyl enol ethers as bifunctional nucleophilic equivalents for oxygen heterocycle synthesis

  摘要：

  DOI：

  10.1016/s0040-4039(00)94538-6

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.
• MARTIN, VAN A.;PERRON, FRANCOISE;ALBIZATI, KIM F., TETRAHEDRON LETT., 31,(1990) N, C. 301-304
  作者：MARTIN, VAN A.、PERRON, FRANCOISE、ALBIZATI, KIM F.

  DOI：——

  日期：——