6-Acetyl-5-hydroxy-4-methoxy-9-methyl-9,10-dihydro-8H-benzo[b]naphtho[2,1-d]furan-7-one | 326803-11-6

• 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: 6-Acetyl-5-hydroxy-4-methoxy-9-methyl-9,10-dihydro-8H-benzo[b]naphtho[2,1-d]furan-7-one
• 英文别名: 6-acetyl-5-hydroxy-4-methoxy-9-methyl-9,10-dihydro-8H-naphtho[1,2-b][1]benzofuran-7-one
• CAS: 326803-11-6
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: SZMRHSLQTIFTON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-Acetyl-5-hydroxy-4-methoxy-9-methyl-9,10-dihydro-8H-benzo[b]naphtho[2,1-d]furan-7-one 在 sodium hydroxide 、 三氯化铝 、 palladium diacetate 、 三乙胺 、 乙硫醇 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 31.5h， 生成 dehydrorabelomycin
  参考文献：
  名称：

  A General Approach to Angucyclines: Synthesis of Hatomarubigin A, Rubiginone B2, Antibiotic X-1488E, 6-Hydroxytetrangulol, and Tetrangulol

  摘要：

  Hatomarubigin A was prepared in 41% yield in a single procedure from acyl naphthoquinone 15 and 5-methylcyclohexane-1,3-dione (16). The net reaction consists of Michael addition to an acyl quinone followed by intramolecular aldol condensation. Hatomarubigin A then served as a common intermediate in syntheses of the angucyclinone antibiotics rubiginone B2, antibiotic X-1488E, 6-hydroxy-tetrangulol, and tetrangulol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00869-3
• 作为产物：
  描述：

  5-甲基环己烷-1,3-二酮 、 3-acetyl-5-methoxy-1,4-naphthoquinone 在 乙醇 、 sodium hydride 、 potassium carbonate 、 碘甲烷 作用下， 以 丙酮 为溶剂， 反应 3.5h， 以76%的产率得到6-Acetyl-5-hydroxy-4-methoxy-9-methyl-9,10-dihydro-8H-benzo[b]naphtho[2,1-d]furan-7-one
  参考文献：
  名称：

  A General Approach to Angucyclines: Synthesis of Hatomarubigin A, Rubiginone B2, Antibiotic X-1488E, 6-Hydroxytetrangulol, and Tetrangulol

  摘要：

  Hatomarubigin A was prepared in 41% yield in a single procedure from acyl naphthoquinone 15 and 5-methylcyclohexane-1,3-dione (16). The net reaction consists of Michael addition to an acyl quinone followed by intramolecular aldol condensation. Hatomarubigin A then served as a common intermediate in syntheses of the angucyclinone antibiotics rubiginone B2, antibiotic X-1488E, 6-hydroxy-tetrangulol, and tetrangulol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00869-3

文献信息

• A General Approach to Angucyclines: Synthesis of Hatomarubigin A, Rubiginone B2, Antibiotic X-1488E, 6-Hydroxytetrangulol, and Tetrangulol
  作者：Kathlyn A Parker、Qing-jie Ding

  DOI：10.1016/s0040-4020(00)00869-3

  日期：2000.12

  Hatomarubigin A was prepared in 41% yield in a single procedure from acyl naphthoquinone 15 and 5-methylcyclohexane-1,3-dione (16). The net reaction consists of Michael addition to an acyl quinone followed by intramolecular aldol condensation. Hatomarubigin A then served as a common intermediate in syntheses of the angucyclinone antibiotics rubiginone B2, antibiotic X-1488E, 6-hydroxy-tetrangulol, and tetrangulol. (C) 2000 Elsevier Science Ltd. All rights reserved.