5-methyl-2[(2-propynyl)thio]methylfuran | 1197850-44-4

• 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: 5-methyl-2[(2-propynyl)thio]methylfuran
• 英文别名: 2-Methyl-5-(prop-2-ynylsulfanylmethyl)furan
• CAS: 1197850-44-4
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: GMNDBIFCRNUQBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 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：
  38.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-2[(2-propynyl)thio]methylfuran 在 potassium tert-butylate 、 氯化铵 作用下， 以 叔丁醇 、 乙醚 、 水 为溶剂， 反应 0.67h， 以79%的产率得到2-methyl-5-(propa-1,2-dienylthiomethyl)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
• 作为产物：
  描述：

  3-溴丙炔 、 5-methyl-2-(acetylthio)methylfuran 在 potassium tert-butylate 、 氯化铵 作用下， 以 叔丁醇 、 乙醚 、 水 为溶剂， 反应 0.33h， 以62%的产率得到5-methyl-2[(2-propynyl)thio]methylfuran
  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