5,7,12-Trioxapentacyclo[11.7.0.02,10.04,8.014,19]icosa-1(13),2,4(8),9,14,16,18-heptaene-11,20-dione | 884902-27-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 5,7,12-Trioxapentacyclo[11.7.0.02,10.04,8.014,19]icosa-1(13),2,4(8),9,14,16,18-heptaene-11,20-dione
• CAS: 884902-27-6
• 化学式: C₁₇H₈O₅
• 分子量: 292.248
• InChiKey: NRVCNIXENHXRFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7,12-Trioxapentacyclo[11.7.0.02,10.04,8.014,19]icosa-1(13),2,4(8),9,14,16,18-heptaene-11,20-dione 、 N,N-二甲基-1,3-二氨基丙烷 以 氯仿 为溶剂， 反应 16.0h， 以45%的产率得到6-(3-Dimethylamino-propyl)-3-nitro-6H-indeno[1,2-c]isoquinoline-5,11-dione
  参考文献：
  名称：

  Synthesis of benz[d]indeno[1,2-b]pyran-5,11-diones: Versatile intermediates for the design and synthesis of topoisomerase I inhibitors

  摘要：

  A method has been developed that relies on a two-step, one-pot condensation between phthalide and 2-carboxybenzaldehydes to provide benz[a]indeno[ 1,2-h]pyran-5,11-diones in a multi-gram fashion. Treatment of these compounds with a primary amine allows rapid access to various N-substituted indenoisoquinolines, whose in vitro anticancer activity and topoisomerase I inhibition have been evaluated. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.008
• 作为产物：
  描述：

  4,5-methylendioxyphtalaldehydic acid 在 盐酸 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙酸乙酯 、 苯 为溶剂， 反应 25.0h， 生成 5,7,12-Trioxapentacyclo[11.7.0.02,10.04,8.014,19]icosa-1(13),2,4(8),9,14,16,18-heptaene-11,20-dione
  参考文献：
  名称：

  Synthesis of benz[d]indeno[1,2-b]pyran-5,11-diones: Versatile intermediates for the design and synthesis of topoisomerase I inhibitors

  摘要：

  A method has been developed that relies on a two-step, one-pot condensation between phthalide and 2-carboxybenzaldehydes to provide benz[a]indeno[ 1,2-h]pyran-5,11-diones in a multi-gram fashion. Treatment of these compounds with a primary amine allows rapid access to various N-substituted indenoisoquinolines, whose in vitro anticancer activity and topoisomerase I inhibition have been evaluated. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.008

文献信息

• Synthesis of benz[d]indeno[1,2-b]pyran-5,11-diones: Versatile intermediates for the design and synthesis of topoisomerase I inhibitors
  作者：Andrew Morrell、Smitha Antony、Glenda Kohlhagen、Yves Pommier、Mark Cushman

  DOI：10.1016/j.bmcl.2006.01.008

  日期：2006.4

  A method has been developed that relies on a two-step, one-pot condensation between phthalide and 2-carboxybenzaldehydes to provide benz[a]indeno[ 1,2-h]pyran-5,11-diones in a multi-gram fashion. Treatment of these compounds with a primary amine allows rapid access to various N-substituted indenoisoquinolines, whose in vitro anticancer activity and topoisomerase I inhibition have been evaluated. (C) 2006 Elsevier Ltd. All rights reserved.