(R,E)-3-(4-(tert-butyldimethylsilyloxy)but-2-enoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one | 1108203-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,E)-3-(4-(tert-butyldimethylsilyloxy)but-2-enoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one
• 英文别名: (4R)-3-[(E)-4-[tert-butyl(dimethyl)silyl]oxybut-2-enoyl]-5,5-diphenyl-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 1108203-24-2
• 化学式: C₂₈H₃₇NO₄Si
• 分子量: 479.692
• InChiKey: NQFSDNFBLCSBCU-KOFSXRQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,E)-3-(4-(tert-butyldimethylsilyloxy)but-2-enoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one 、 天然橡胶 在 氯化二乙基铝 作用下， 以 正己烷 、 甲苯 为溶剂， 以94%的产率得到(R)-3-((1R,6R)-6-((tert-butyldimethylsilyloxy)methyl)-4-methylcyclohex-3-enecarbonyl)-4-isopropyl-5,5-diphenyloxazolidin-2-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：

  (E)-4-((tert-butyldimethylsilyl)oxy)but-2-enoic acid 、 (R)-4-异丙基-5,5-二苯基-2-恶唑烷酮 在 三甲基乙酰氯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 以19.59 g的产率得到(R,E)-3-(4-(tert-butyldimethylsilyloxy)but-2-enoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-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.