1-hydroxy-6,6-dimethyl-6H-naphtho[1,2-c]furan-3,9-(1H,6H)-dione | 915026-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 1-hydroxy-6,6-dimethyl-6H-naphtho[1,2-c]furan-3,9-(1H,6H)-dione
• 英文别名: 1-hydroxy-6,6-dimethyl-1H-benzo[e][2]benzofuran-3,9-dione
• CAS: 915026-96-9
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: JSKMNBRQJOBKOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-hydroxy-6,6-dimethyl-6H-naphtho[1,2-c]furan-3,9-(1H,6H)-dione 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 生成 6,6-dimethyl-6H-naphtho[1,2-c]furan-1,3,9-trione
  参考文献：
  名称：

  Total Synthesis of (±)-Hyphodermins A and D

  摘要：

  An efficient formal synthesis of (+/-)-hyphodermins A and D, metabolites of Hyphoderma radula, has been completed in 12 and 11 steps, respectively. The tricyclic carbon skeleton of enone 6 was rapidly assembled from diester 11 via an alpha brominationn-elimination sequence followed by anhydride formation. Regioselective reduction of the lactone group of enone 6 with LiAlH(t-BUO)(3) gave lactol 15. Lactol 15 was converted in two steps to (+/-)-hyphodermin D, without the need for complex protection-deprotection strategies. Lactol 15 was converted in three steps to (+/-)-hyphodermin A, via the key step of epoxidation of an enone in the presence of a THP lactol. A combination of NMR and ab initio studies suggests that the structures of hyphodermin C and D should be interchanged.

  DOI：

  10.1021/jo800227p
• 作为产物：
  描述：

  6,6-dimethyl-6H-naphtho[1,2-c]furan-1,3,9-trione 在 lithium tri(tert-butoxy)alumiunum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以112 mg的产率得到1-hydroxy-6,6-dimethyl-6H-naphtho[1,2-c]furan-3,9-(1H,6H)-dione
  参考文献：
  名称：

  Total Synthesis of (±)-Hyphodermins A and D

  摘要：

  An efficient formal synthesis of (+/-)-hyphodermins A and D, metabolites of Hyphoderma radula, has been completed in 12 and 11 steps, respectively. The tricyclic carbon skeleton of enone 6 was rapidly assembled from diester 11 via an alpha brominationn-elimination sequence followed by anhydride formation. Regioselective reduction of the lactone group of enone 6 with LiAlH(t-BUO)(3) gave lactol 15. Lactol 15 was converted in two steps to (+/-)-hyphodermin D, without the need for complex protection-deprotection strategies. Lactol 15 was converted in three steps to (+/-)-hyphodermin A, via the key step of epoxidation of an enone in the presence of a THP lactol. A combination of NMR and ab initio studies suggests that the structures of hyphodermin C and D should be interchanged.

  DOI：

  10.1021/jo800227p

文献信息

• Total Synthesis of (±)-Hyphodermins A and D
  作者：Wendy A. Loughlin、Ian D. Jenkins、Luke C. Henderson、Marc R. Campitelli、Peter C. Healy

  DOI：10.1021/jo800227p

  日期：2008.5.1

  An efficient formal synthesis of (+/-)-hyphodermins A and D, metabolites of Hyphoderma radula, has been completed in 12 and 11 steps, respectively. The tricyclic carbon skeleton of enone 6 was rapidly assembled from diester 11 via an alpha brominationn-elimination sequence followed by anhydride formation. Regioselective reduction of the lactone group of enone 6 with LiAlH(t-BUO)(3) gave lactol 15. Lactol 15 was converted in two steps to (+/-)-hyphodermin D, without the need for complex protection-deprotection strategies. Lactol 15 was converted in three steps to (+/-)-hyphodermin A, via the key step of epoxidation of an enone in the presence of a THP lactol. A combination of NMR and ab initio studies suggests that the structures of hyphodermin C and D should be interchanged.