(3aS,7aS)-6-methyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one | 1197850-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (3aS,7aS)-6-methyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one
• 英文别名: (3aS,7aS)-6-methyl-3a,4,5,7a-tetrahydro-3H-1-benzofuran-2-one
• CAS: 1197850-94-4
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: ROXSEEKHVHAOCP-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aS,7aS)-6-methyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one 、 碘甲烷 在 lithium diisopropyl amide 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 以28%的产率得到(3R,3aS,7aS)-3,6-dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one
  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：

  2-[(1RS,2S)-2-hydroxy-4-methylcyclohex-3-enyl]acetic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以150 mg的产率得到6-methyl-3a,4,5,7a-tetrahydrobenzofuran-2(3H)-one
  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

文献信息

• Total Synthesis of Racemic Laurenditerpenol, an HIF-1 Inhibitor
  作者：Michael E. Jung、G-Yoon Jamie Im

  DOI：10.1021/jo902029x

  日期：2009.11.20

  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.