ethyl 2-acetyl-4-(3,6-dimethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)butanoate | 1418210-03-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-acetyl-4-(3,6-dimethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)butanoate
• CAS: 1418210-03-3
• 化学式: C₂₃H₃₀O₆
• 分子量: 402.488
• InChiKey: OLDRXJZVEPTFRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  5-甲基环己烷-1,3-二酮 、 ethyl 2-butoxy-6-methyl-3,4-dihydro-2H-pyran-5-carboxylate 在 葡糖酸 作用下， 以 水 为溶剂， 反应 11.0h， 以85%的产率得到ethyl 2-acetyl-4-(3,6-dimethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)butanoate
  参考文献：
  名称：

  Gluconic acid aqueous solution: a task-specific bio-based solvent for ring-opening reactions of dihydropyrans

  摘要：

  Gluconic acid aqueous solution (GAAS) that is a largely available bio-based chemical was proved to be an effective task-specific medium for ring-opening reactions of dihydropyrans. In the presence of nucleophiles, such as indoles, 1,3-cyclohexanediones, N,N-dimethylaniline, N-methylaniline, 2-naphthol, and resorcin, a series of 2-substituted 1, 3-dicarbonyl compounds were synthesized in good to excellent yields. The first example of ring-opening of oxa-Pictet-Spengler product with nucleophiles was also described. These results not only demonstrate the feasibility of using GAAS as a sustainable solvent, but also offer an effective way for the ring-opening reactions of dihydropyrans with nucleophiles. Because these reactions proceeded with excellent atom-economy in a sustainable bio-based solvent, the present method was thus characterized by many properties of green chemistry, such as green solvent, atom-economy, and utilization of bio-based chemicals. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.076