(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 | 1108203-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• 英文别名: [(E,1R)-3-(2,2-dimethyl-6-oxo-1,3-dioxin-4-yl)-1-[(1R,2S,4R)-2-[(1E,3E)-hexa-1,3,5-trienyl]-4-methylcyclohexyl]prop-2-enyl] methyl carbonate
• CAS: 1108203-34-4
• 化学式: C₂₄H₃₂O₆
• 分子量: 416.514
• InChiKey: NZIAATNXWVKSCD-XHDFYOGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (R,E)-3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-1-((1R,2R,4R)-2-formyl-4-methylcyclohexyl)allyl methyl carbonate 、 2,4-pentadienyl triphenyl phosphonium bromide 在 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 反应 0.75h， 以66%的产率得到(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
  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.