methyl 3-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-9-(methoxycarbonyloxy)-6-methyl-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-1-yl)-3-oxopropanoate | 1108203-35-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 3-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-9-(methoxycarbonyloxy)-6-methyl-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-1-yl)-3-oxopropanoate
• 英文别名: methyl 3-[(1S,2S,4aS,4bS,6R,8aR,9S,9aS)-2-ethenyl-9-methoxycarbonyloxy-6-methyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-1-yl]-3-oxopropanoate
• CAS: 1108203-35-5
• 化学式: C₂₂H₃₀O₆
• 分子量: 390.477
• InChiKey: GMFRSCYVNIYCKT-UZFUXEBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 (R,E)-3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-1-((1R,2S,4R)-2-((1E,3E)-hexa-1,3,5-trienyl)-4-methylcyclohexyl)allyl methyl carbonate 以 甲苯 为溶剂， 反应 1.5h， 以85%的产率得到methyl 3-((1S,2S,4aS,4bS,6R,8aR,9S,9aS)-9-(methoxycarbonyloxy)-6-methyl-2-vinyl-2,4a,4b,5,6,7,8,8a,9,9a-decahydro-1H-fluoren-1-yl)-3-oxopropanoate
  参考文献：
  名称：

  A Rapid, Asymmetric Synthesis of the Decahydrofluorene Core of the Hirsutellones

  摘要：

  A tandem ketene-trapping/Diels-Alder cyclization sequence was the pivotal transformation in an efficient, asymmetric synthesis of a decahydrofluorene tricyclic structure possessing eight stereogenic centers and key features of the hirsutellone class of antitubercular natural products. The hirsutellone-like beta-keto ester that was fashioned by this sequence (13 steps; 6% overall yield) demonstrated significant inhibitory activity against Mycobacterium tuberculosis. The mechanism of action of this antitubercular compound is not yet known.

  DOI：

  10.1021/ol802768p

文献信息

• A Rapid, Asymmetric Synthesis of the Decahydrofluorene Core of the Hirsutellones
  作者：S. David Tilley、Keith P. Reber、Erik J. Sorensen

  DOI：10.1021/ol802768p

  日期：2009.2.5

  A tandem ketene-trapping/Diels-Alder cyclization sequence was the pivotal transformation in an efficient, asymmetric synthesis of a decahydrofluorene tricyclic structure possessing eight stereogenic centers and key features of the hirsutellone class of antitubercular natural products. The hirsutellone-like beta-keto ester that was fashioned by this sequence (13 steps; 6% overall yield) demonstrated significant inhibitory activity against Mycobacterium tuberculosis. The mechanism of action of this antitubercular compound is not yet known.