8-hydroxy-3,4-dihydro-2H-anthracene-1,9,10-trione | 37802-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 8-hydroxy-3,4-dihydro-2H-anthracene-1,9,10-trione
• 英文别名: 8-Hydroxy-3,4-dihydro-2H-anthracen-1,9,10-trion；8-Hydroxy-2,3-dihydro-1,9,10(2H)-anthracentrion；8-hydroxy-3,4-dihydro-2H-anthracene-1,9,10-trione
• CAS: 37802-99-6
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: UMUBXPULDVHYRY-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：
  0.21
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-hydroxy-3,4-dihydro-2H-anthracene-1,9,10-trione 反应 730.5h， 以86%的产率得到3a,3b,4,5-tetrahydro-1,7,8,17-tetrahydroxy-2H-dibenzo[c,mn]naphtho[2,3-g]xanthene-6,13,18(3H)-trione
  参考文献：
  名称：

  Efficient Syntheses of Rugulosin Analogues

  摘要：

  [GRAPHICS]Oxidation of 3b or 14c,d with Pb(OAc)(4) in AcOH for 20 min at 25 degrees C and 1 h at 75 degrees C gave flavoskyrin-type dimers 6b and 15c,d in 53-86% yield. Heating a solution of 6b or 15c,d in pyridine under air for 1 h at 75-80 degrees C and then for 1-2 h at 110 degrees C afforded rugulosin-type dimers 10b and 17c,d in 61-88% yield. This two-step sequence provides a practical route to this unusual natural product skeleton.

  DOI：

  10.1021/jo0508898
• 作为产物：
  描述：

  1,8-二羟基蒽醌 在 palladium on activated charcoal lead(IV) acetate 、 sodium hydroxide 、 氢气 、 溶剂黄146 作用下， 以 水 为溶剂， 25.0 ℃ 、344.74 kPa 条件下， 反应 25.33h， 生成 8-hydroxy-3,4-dihydro-2H-anthracene-1,9,10-trione
  参考文献：
  名称：

  Efficient Syntheses of Rugulosin Analogues

  摘要：

  [GRAPHICS]Oxidation of 3b or 14c,d with Pb(OAc)(4) in AcOH for 20 min at 25 degrees C and 1 h at 75 degrees C gave flavoskyrin-type dimers 6b and 15c,d in 53-86% yield. Heating a solution of 6b or 15c,d in pyridine under air for 1 h at 75-80 degrees C and then for 1-2 h at 110 degrees C afforded rugulosin-type dimers 10b and 17c,d in 61-88% yield. This two-step sequence provides a practical route to this unusual natural product skeleton.

  DOI：

  10.1021/jo0508898

文献信息

• Shibata et al., Pharmaceutical Bulletin, 1956, vol. 4, p. 303,308
  作者：Shibata et al.

  DOI：——

  日期：——
• Shibata,S.; Kitagawa,I., Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 884 - 888
  作者：Shibata,S.、Kitagawa,I.

  DOI：——

  日期：——
• Efficient Syntheses of Rugulosin Analogues
  作者：Barry B. Snider、Xiaolei Gao

  DOI：10.1021/jo0508898

  日期：2005.8.1

  [GRAPHICS]Oxidation of 3b or 14c,d with Pb(OAc)(4) in AcOH for 20 min at 25 degrees C and 1 h at 75 degrees C gave flavoskyrin-type dimers 6b and 15c,d in 53-86% yield. Heating a solution of 6b or 15c,d in pyridine under air for 1 h at 75-80 degrees C and then for 1-2 h at 110 degrees C afforded rugulosin-type dimers 10b and 17c,d in 61-88% yield. This two-step sequence provides a practical route to this unusual natural product skeleton.