12b-methyl-2,3-dihydro-8,11-dimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one | 188648-37-5

• 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-8,11-dimethoxy-1H-benzo[6,7]phenanthro[10,1-bc]furan-6-(12bH)-one
• 英文别名: (+/-)-xestoquinol dimethyl ether；5,8-Dimethoxy-1-methyl-14-oxapentacyclo[11.6.1.02,11.04,9.016,20]icosa-2,4,6,8,10,13(20),15-heptaen-12-one
• CAS: 188648-37-5
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: IPVMJHCYMXESQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12b-methyl-2,3-dihydro-8,11-dimethoxy-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63%的产率得到(+/-)-xestoquinone
  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：

  4,7-dimethoxybenzofuran 在 palladium on activated charcoal 氢气 、 sodium 、 四氯苯醌 、 碳酸氢钠 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 xylene 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 98.75h， 生成 12b-methyl-2,3-dihydro-8,11-dimethoxy-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

• Formal total synthesis of xestoquinone via furan ring transfer reaction strategy
  作者：Ken Kanematsu、Seizo Soejima、Guilin Wang

  DOI：10.1016/s0040-4039(00)92301-3

  日期：1991.1

  A formal total synthesis of the marine natural product xestoquinone (5) based upon FRT reaction strategy is accomplished by preparation of the pentacyclic furan 6, an advanced key intermediate in Harada's previous total synthesis of this target.

  基于FRT反应策略的海洋天然产物xestoquinone（5）的正式总合成是通过制备五环呋喃6来完成的，该五环呋喃是原田原先对该目标的总合成中的高级关键中间体。
• Intramolecular Diels−Alder and Cope Reactions of <i>o</i>-Quinonoid Monoketals and Their Adducts:  Efficient Syntheses of (±)-Xestoquinone and Heterocycles Related to Viridin
  作者：Rina Carlini、Kerianne Higgs、Christina Older、Sab Randhawa、Russell Rodrigo

  DOI：10.1021/jo970394l

  日期：1997.4.1
• 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.