(1β,6β)-2,2-(1,2-Ethylenedioxy)-1-methyl-9-carbomethoxybicyclo<4.4.0>decan-8-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1β,6β)-2,2-(1,2-Ethylenedioxy)-1-methyl-9-carbomethoxybicyclo<4.4.0>decan-8-one
• 英文别名: methyl (4'aS,8'aR)-3'-hydroxy-8'a-methylspiro[1,3-dioxolane-2,8'-1,4,4a,5,6,7-hexahydronaphthalene]-2'-carboxylate
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: ADYVBNMSHQXQGS-IINYFYTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3',4',8',8'a-tetrahydro-8'a-methylspiro[1,3-dioxolane-2,1'(2'H)-naphthalen]-6'(7'H)-one 在 Lindlar's catalyst 氢气 、 sodium hydride 作用下， 以 吡啶 、 乙二醇二甲醚 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 51.0h， 生成 (1β,6β)-2,2-(1,2-Ethylenedioxy)-1-methyl-9-carbomethoxybicyclo<4.4.0>decan-8-one
  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

文献信息

• Effect of C-9 Substituents on the Regioselectivity of A-Ring Reactions in Derivatives of the Wieland-Miescher Ketone
  作者：Kwangyong Park、William J. Scott、David F. Wiemer

  DOI：10.1021/jo00100a037

  日期：1994.10

  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.