(+/-)-(1R,2R,3S,4S)-methyl 1,4-dimethyl-3-((phenoxycarbonothioyloxy)methyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylate

• 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: (+/-)-(1R,2R,3S,4S)-methyl 1,4-dimethyl-3-((phenoxycarbonothioyloxy)methyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylate
• 英文别名: methyl (1R,2R,3S,4S)-1,4-dimethyl-3-(phenoxycarbothioyloxymethyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylate
• 化学式: C₁₈H₂₂O₅S
• 分子量: 350.436
• InChiKey: YXKYAOSQQAOYEZ-IDCJVQTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (+/-)-(1R,2R,3S,4S)-methyl 3-(hydroxymethyl)-1,4-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylate 、 硫代氯甲酸苯酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到(+/-)-(1R,2R,3S,4S)-methyl 1,4-dimethyl-3-((phenoxycarbonothioyloxy)methyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylate
  参考文献：
  名称：

  Total Synthesis of Racemic Laurenditerpenol, an HIF-1 Inhibitor

  摘要：

  The convergent total synthesis of the HIF-1 inhibitor laurenditerpenol 1 and its diastereomer 1' is reported. The key step involves the Julia-Kocienski olefination-reduction process between the sulfone 55 and the aldehyde 54. The unusual trimethylated oxanorbornane sulfone 55 was successfully synthesized from the known exo Diels-Alder adduct 24 of 2,5-dimethylfuran 7 and maleic anhydride 23 in 8 steps. The aldehyde 54 was prepared by ring-opening and elaboration of lactone 41. In addition, four analogues of I were also successfully synthesized for biological testing.

  DOI：

  10.1021/jo902029x