tert-butyl(((1R,2R,5R)-2-((E)-2-methoxyvinyl)-5-methylcyclohexyl)methoxy)dimethylsilane | 1108203-29-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl(((1R,2R,5R)-2-((E)-2-methoxyvinyl)-5-methylcyclohexyl)methoxy)dimethylsilane
• 英文别名: tert-butyl-[[(1R,2R,5R)-2-[(E)-2-methoxyethenyl]-5-methylcyclohexyl]methoxy]-dimethylsilane
• CAS: 1108203-29-7
• 化学式: C₁₇H₃₄O₂Si
• 分子量: 298.541
• InChiKey: IWTNDXFBJWWVKW-WHVDOQMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,2R,4R)-2-((tert-butyldimethylsilyloxy)methyl)-4-methylcyclohexanecarbaldehyde 、 甲氧基甲基三苯基氯化膦 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 tert-butyl(((1R,2R,5R)-2-((Z)-2-methoxyvinyl)-5-methylcyclohexyl)methoxy)dimethylsilane 、 tert-butyl(((1R,2R,5R)-2-((E)-2-methoxyvinyl)-5-methylcyclohexyl)methoxy)dimethylsilane
  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.