2-methyl-5-[(2-propynylsulfonyl)methyl]furan | 1197850-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-methyl-5-[(2-propynylsulfonyl)methyl]furan
• 英文别名: 2-Methyl-5-(prop-2-ynylsulfonylmethyl)furan
• CAS: 1197850-47-7
• 化学式: C₉H₁₀O₃S
• 分子量: 198.243
• InChiKey: XVLLWPUNBQCCFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-5-[(2-propynylsulfonyl)methyl]furan 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成
  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
• 作为产物：
  描述：

  5-methyl-2[(2-propynyl)thio]methylfuran 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以36%的产率得到2-methyl-5-[(2-propynylsulfonyl)methyl]furan
  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