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 | 1108203-30-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 6-[(E,3R)-3-[(1R,2R,4R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methylcyclohexyl]-3-hydroxyprop-1-enyl]-2,2-dimethyl-1,3-dioxin-4-one
• CAS: 1108203-30-0
• 化学式: C₂₃H₄₀O₅Si
• 分子量: 424.653
• InChiKey: RDPKKDHGXCBIKM-AYEAEKMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  、 2,2-(dimethyl)-6-[(triphenylphosphoranylidene)methyl]-4H-1,3-dioxin-4-one 以 二氯甲烷 、 乙腈 为溶剂， 生成 6-((S,E)-3-((1R,2R,4R)-2-((tert-butyldimethylsilyloxy)methyl)-4-methylcyclohexyl)-3-hydroxyprop-1-enyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 、 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
  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.