(4AS,7R,7AS)-7-Methyl-3-oxooctahydrocyclopenta[C]pyran-1-YL acetate | 134906-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4AS,7R,7AS)-7-Methyl-3-oxooctahydrocyclopenta[C]pyran-1-YL acetate
• 英文别名: [(4aS,7R,7aS)-7-methyl-3-oxo-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-1-yl] acetate
• CAS: 134906-69-7；135027-51-9
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: SRCCTASIBNBMPD-SGVDYLPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (3aS*,4R*,6aS*)-1,3a,4,5,6,6a-hexahydro-4-methyl-2-<(trimethylsilyl)oxy>pentalene 在 二甲基硫 、 三氟化硼乙醚 、 臭氧 作用下， 反应 3.0h， 生成 (4AS,7R,7AS)-7-Methyl-3-oxooctahydrocyclopenta[C]pyran-1-YL acetate
  参考文献：
  名称：

  Cyclopentenyllithium additions to chiral aldehydes. Diastereofacial selectivity indicating the absence of a pronounced neighboring carboxylate anion effect

  摘要：

  The 1,2-addition of cyclopentenyllithium to a series of three five-membered aldehydo esters and their hemiacylals has been examined in order to assess the level and direction of facial selectivity surrounding nucleophilic attack at the aldehyde carbonyl and to clarify possible electronic and steric contributions stemming from neighboring functional groups. Neither methyl substitution of the acetic acid (ester) side chain nor the interchange of ester for carboxylate anion serve as important diastereocontrol elements. Instead, diastereofacial selectivity in these and related cyclic carboxaldehydes is governed by the inherent structural features of the ring system to which the functional group is attached. The convenient preparation of a complete subset of isomerically pure bicyclic lactones carrying five stereogenic centers is reported.

  DOI：

  10.1021/jo00012a013