(1R*,11S*,12R*,16S*)-1-(methoxycarbonyl)-12-propyl-18-oxatricyclo<9.5.1.1^12,16>octadecan-16-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1R*,11S*,12R*,16S*)-1-(methoxycarbonyl)-12-propyl-18-oxatricyclo<9.5.1.1^12,16>octadecan-16-one
• 英文别名: methyl (1R,11S,12R,16S)-17-oxo-12-propyl-18-oxatricyclo[9.5.1.112,16]octadecane-1-carboxylate
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: YXGPBHBDONXGKZ-GMQQQROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 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-氧代环十二烷-1-羧酸甲酯 在 triphenylmethylium hexachloroantimonate(V) 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (1R*,11S*,12R*,16S*)-1-(methoxycarbonyl)-12-propyl-18-oxatricyclo<9.5.1.1^12,16>octadecan-16-one
  参考文献：
  名称：

  Synthesis of Cyclic Bis(trimethysilyl) Enol Ethers and Their [3 + 4] and [3 + 5] Annulation Reactions with Dicarbonyl Electrophiles. Access to Highly Functionalized Tricyclic Ethers Possessing Trans Intrabridgehead Stereochemistry

  摘要：

  The synthesis of cyclic bis(trimethylsilyl) enol ethers from cycloalkanone carboxylates is described. The [3 + 4] and [3 + 5] annulation reactions of these bis(dinucleophilic), synthons with various 1,4- and 1,5-dicarbonyl electrophiles leads to the formation of tricyclic keto ethers with good regio- and stereochemical control. An interesting trans intrabridgehead stereochemistry is observed when using bis(trimethylsilyl) enol ethers derived from nine- to 12-membered ring beta-keto esters.

  DOI：

  10.1021/jo9902547

文献信息

• Synthesis of Cyclic Bis(trimethysilyl) Enol Ethers and Their [3 + 4] and [3 + 5] Annulation Reactions with Dicarbonyl Electrophiles. Access to Highly Functionalized Tricyclic Ethers Possessing Trans Intrabridgehead Stereochemistry
  作者：Gary A. Molander、Bernard Bessières、Paul R. Eastwood、Bruce C. Noll

  DOI：10.1021/jo9902547

  日期：1999.5.1

  The synthesis of cyclic bis(trimethylsilyl) enol ethers from cycloalkanone carboxylates is described. The [3 + 4] and [3 + 5] annulation reactions of these bis(dinucleophilic), synthons with various 1,4- and 1,5-dicarbonyl electrophiles leads to the formation of tricyclic keto ethers with good regio- and stereochemical control. An interesting trans intrabridgehead stereochemistry is observed when using bis(trimethylsilyl) enol ethers derived from nine- to 12-membered ring beta-keto esters.