methyl (7E)-7-(tert-butyl-2',2'-dimethyl-4'-oxo-3'aβ,5',6'α,6'aβ-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-ylidene)heptanoate | 133230-24-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (7E)-7-(tert-butyl-2',2'-dimethyl-4'-oxo-3'aβ,5',6'α,6'aβ-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-ylidene)heptanoate
• CAS: 133230-24-7
• 化学式: C₂₀H₃₂O₅
• 分子量: 352.471
• InChiKey: QHVLTMVGOJHFBA-SOANQCLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 生成 methyl (7E)-7-(tert-butyl-2',2'-dimethyl-4'-oxo-3'aβ,5',6'α,6'aβ-tetrahydro-4'H-cyclopenta-1',3'-dioxol-5'-ylidene)heptanoate
  参考文献：
  名称：

  Development of a triply convergent aldol approach to prostanoids

  摘要：

  Various organocopper-mediated methods for the conjugate addition of alkyl and alkenyl groups to enone 1 to provide cyclopentanones 4 were studied. A variety of aldol-based procedures for the production of ketones 3 was evaluated, including a two-pot procedure involving generation of lithium enolates from 4, one-pot conjugate additions/aldol condensations methods, and methods involving the intermediate production of silyl enol ethers. The most promising procedure was found to be that involving trapping of the initial enolates from 1 as enol acetates and regeneration of enolates with methyllithium followed by aldol and dehydration reactions.

  DOI：

  10.1021/jo00010a031