(4aS,8aS)-5,8a-Dimethyl-hexahydro-naphthalene-1,6-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,8aS)-5,8a-Dimethyl-hexahydro-naphthalene-1,6-dione
• 英文别名: (4aS,8aS)-5,8a-dimethyl-3,4,4a,5,7,8-hexahydro-2H-naphthalene-1,6-dione
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: BAPYGQXRXLEUKO-XSSOSWMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,8a-二甲基-3,4,8,8a-四氢-1,6-(2H,7H)-萘二酮 在 Lindlar's catalyst 氢气 作用下， 以 吡啶 为溶剂， 反应 48.0h， 生成 (4aS,8aS)-5,8a-Dimethyl-hexahydro-naphthalene-1,6-dione 、 (1β,6β,7α)-1,7-Dimethylbicyclo<4.4.0>decane-2,8-dione 、 (1β,6β,7β)-1,7-Dimethylbicyclo<4.4.0>decane-2,8-dione
  参考文献：
  名称：

  Effect of C-9 Substituents on the Regioselectivity of A-Ring Reactions in Derivatives of the Wieland-Miescher Ketone

  摘要：

  The nature of C-9 substituents Was found to have a significant influence on the regio- and stereochemistry of A-ring reactions in a variety of Wieland-Miescher ketone derivatives. For example, Pd-catalyzed hydrogenation of the C-9 dioxolanes resulted in much better selectivity for the cis-funded products vis-a-vis the corresponding C-9 ketone, with the parent Wieland-Miescher ketone itself and both C-4 methyl and C-4 carboalkoxy substituted analogues. In addition, methylation and acylation of A-ring enolates favored the C-2 isomer when a C-9 dioxolane group was present, but the C-4 substituted isomer was predominant with the corresponding C-9 ketone. These differences in regiochemistry may allow selective elaboration of cis-fused decalins during preparation of complex natural products.

  DOI：

  10.1021/jo00100a037