12b-methyl-2,3-dihydro-8,9,11-trimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one | 328267-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 12b-methyl-2,3-dihydro-8,9,11-trimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one
• CAS: 328267-98-7
• 化学式: C₂₃H₂₂O₅
• 分子量: 378.425
• InChiKey: XXHUYMGSFLKXEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.9
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  12b-methyl-2,3-dihydro-8,9,11-trimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 以60%的产率得到(+/-)-9-methoxyxestoquinone
  参考文献：
  名称：

  Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives

  摘要：

  Syntheses of (+/-)-xestoquinone, (+/-)-9-methoxyxestoquinone and (+/-)-10-methoxyxestoquinone are described. A convergent CD plus ABE plan using the appropriate isobenzofuran (CD) and naphthofuranone (ABE) has been implemented to provide these marine metabolites in overall yields of 18.3, 9.5 and 8.5%, respectively. The latter pair of compounds, previously evaluated as inhibitors of Topoisomerase II as an inseparable mixture, are now available separate and pure for the first time. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00938-8
• 作为产物：
  描述：

  1,2,4-三甲氧基苯 在 palladium on activated charcoal 氢气 、 溴 、 四氯苯醌 、 3,6-二-2-吡啶基-1,2,4,5-四嗪 、 sodium hydride 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 乙酸乙酯 、 xylene 为溶剂， 55.0 ℃ 、101.33 kPa 条件下， 反应 97.25h， 生成 12b-methyl-2,3-dihydro-8,9,11-trimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one
  参考文献：
  名称：

  Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives

  摘要：

  Syntheses of (+/-)-xestoquinone, (+/-)-9-methoxyxestoquinone and (+/-)-10-methoxyxestoquinone are described. A convergent CD plus ABE plan using the appropriate isobenzofuran (CD) and naphthofuranone (ABE) has been implemented to provide these marine metabolites in overall yields of 18.3, 9.5 and 8.5%, respectively. The latter pair of compounds, previously evaluated as inhibitors of Topoisomerase II as an inseparable mixture, are now available separate and pure for the first time. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00938-8

文献信息

• Isobenzofurans and ortho-benzoquinone monoketals in syntheses of xestoquinone and its 9- and 10-methoxy derivatives
  作者：Hamish S Sutherland、Kerianne C Higgs、Nicholas J Taylor、Russell Rodrigo

  DOI：10.1016/s0040-4020(00)00938-8

  日期：2001.1

  Syntheses of (+/-)-xestoquinone, (+/-)-9-methoxyxestoquinone and (+/-)-10-methoxyxestoquinone are described. A convergent CD plus ABE plan using the appropriate isobenzofuran (CD) and naphthofuranone (ABE) has been implemented to provide these marine metabolites in overall yields of 18.3, 9.5 and 8.5%, respectively. The latter pair of compounds, previously evaluated as inhibitors of Topoisomerase II as an inseparable mixture, are now available separate and pure for the first time. (C) 2000 Elsevier Science Ltd. All rights reserved.