6,6a-dihydro-2,3-diisopropoxy-4,6a-dimethyl-1(H)-pentalenone | 172484-21-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6,6a-dihydro-2,3-diisopropoxy-4,6a-dimethyl-1(H)-pentalenone
• 英文别名: 4,6a-dimethyl-2,3-di(propan-2-yloxy)-5,6-dihydropentalen-1-one
• CAS: 172484-21-8
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: PDOLYHVNWHQQMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,6a-dihydro-2,3-diisopropoxy-4,6a-dimethyl-1(H)-pentalenone 在 盐酸 、 甲醇 、 氢氧化钾 、 lithium aluminium tetrahydride 、 rochelle salt 作用下， 以 四氢呋喃 为溶剂， 反应 2.58h， 生成 (1R*,6aR*)-4,5,6,6a-tetrahydro-3-isopropoxy-1-methoxy-4,6a-dimethyl-2(1H)-pentalenone
  参考文献：
  名称：

  Mapping the Chemical Reactivity of Polyquinanes Produced by 2-fold Addition of Vinyl Anions to Squarate Esters. A Bicyclic Case Study

  摘要：

  A highly oxygenated diquinane representative of the product class obtained from the condensation of squarate esters with a pair of vinyl anions has been subjected to a battery of chemical reactions for the purpose of achieving utilitarian functional group transformations. Reduction with lithium aluminum hydride proceeds predominantly, but not exclusively, by 1,4-reduction. Dehydration of the gamma-hydroxy-alpha,beta-(bisalkoxy)cyclopentenone to extend conjugation into the B ring was achieved via chlorination and subsequent removal of HCl. Access to dienone 12 in this manner has opened the door to reductive removal of the gamma-hydroxyl substituent, to angular methylation, and to allied chemical changes. The global results disclose that the previously unknown functional group array present in 5 and its congeners is amenable to convenient modification, thereby providing the backdrop for more advanced annulation and structural elaboration. The prospects for utilization of the several new compound types as serviceable building blocks are considered to be numerous.

  DOI：

  10.1021/jo9516751
• 作为产物：
  描述：

  (3aR*,4S*,6aR*)-4,5,6,6a-tetrahydro-3a-hydroxy-2,3-diisopropoxy-4,6a-dimethyl-1(3aH)-pentalenone 在 lithium carbonate 、 甲基磺酰氯 、 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 6,6a-dihydro-2,3-diisopropoxy-4,6a-dimethyl-1(H)-pentalenone
  参考文献：
  名称：

  Mapping the Chemical Reactivity of Polyquinanes Produced by 2-fold Addition of Vinyl Anions to Squarate Esters. A Bicyclic Case Study

  摘要：

  A highly oxygenated diquinane representative of the product class obtained from the condensation of squarate esters with a pair of vinyl anions has been subjected to a battery of chemical reactions for the purpose of achieving utilitarian functional group transformations. Reduction with lithium aluminum hydride proceeds predominantly, but not exclusively, by 1,4-reduction. Dehydration of the gamma-hydroxy-alpha,beta-(bisalkoxy)cyclopentenone to extend conjugation into the B ring was achieved via chlorination and subsequent removal of HCl. Access to dienone 12 in this manner has opened the door to reductive removal of the gamma-hydroxyl substituent, to angular methylation, and to allied chemical changes. The global results disclose that the previously unknown functional group array present in 5 and its congeners is amenable to convenient modification, thereby providing the backdrop for more advanced annulation and structural elaboration. The prospects for utilization of the several new compound types as serviceable building blocks are considered to be numerous.

  DOI：

  10.1021/jo9516751