6-((R,E)-3-hydroxy-3-((1R,2R,4R)-2-(hydroxymethyl)-4-methylcyclohexyl)prop-1-enyl)-2,2-dimethyl-4H-1,3-dioxin-4-one | 1108203-46-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-((R,E)-3-hydroxy-3-((1R,2R,4R)-2-(hydroxymethyl)-4-methylcyclohexyl)prop-1-enyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
• CAS: 1108203-46-8
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: GWNKXXYKWBOCLX-QYOMFVPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  三光气 、 6-((R,E)-3-hydroxy-3-((1R,2R,4R)-2-(hydroxymethyl)-4-methylcyclohexyl)prop-1-enyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(1S,5aR,7R,9aR)-1-((E)-2-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)vinyl)-7-methyloctahydrobenzo[e][1,3]dioxepin-3-one
  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：

  6-((R,E)-3-((1R,2R,4R)-2-((tert-butyldimethylsilyloxy)methyl)-4-methylcyclohexyl)-3-hydroxyprop-1-enyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 以92%的产率得到6-((R,E)-3-hydroxy-3-((1R,2R,4R)-2-(hydroxymethyl)-4-methylcyclohexyl)prop-1-enyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
  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