5,9,10-trimethoxy-3-(2-phenylmethoxyethyl)-3,4-dihydro-1H-benzo[g]isochromene | 251938-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 5,9,10-trimethoxy-3-(2-phenylmethoxyethyl)-3,4-dihydro-1H-benzo[g]isochromene
• CAS: 251938-76-8
• 化学式: C₂₅H₂₈O₅
• 分子量: 408.494
• InChiKey: PAHKOSQTCDTEIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,9,10-trimethoxy-3-(2-phenylmethoxyethyl)-3,4-dihydro-1H-benzo[g]isochromene 在 palladium on activated charcoal chromium(VI) oxide 、 4 A molecular sieve 、 氢气 、 lithium perchlorate 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 51.9h， 生成
  参考文献：
  名称：

  Stereoselective, Oxidative C−C Bond Coupling of Naphthopyran Induced by DDQ:  Stereocontrolled Total Synthesis of Deoxyfrenolicin

  摘要：

  A formal total synthesis of pyranonaphthoquinone natural product deoxyfrenolicin 1 is described. The key step in the synthesis involves the use of stereoselective 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-induced C-C bond coupling of the naphthopyran 10 with allyltriphenyltin to give exclusively 1,3 trans naphthopyran derivative 23, The naphthopyran 10 was obtained via oxa-Pictet-Spengler cyclization of substituted naphthalene 22, which was derived by regioselective benzannulation of chromium carbene complex 12 with acetylene 18, This newly developed synthetic route employing a tandem benzannulation/oxa-Pictet-Spengler cyclization/DDQ-induced coupling strategy should also be applicable to the synthesis of other pyranonaphthoquinone natural products such as kalafungin 4 and nanaomycin 5.

  DOI：

  10.1021/ol9909738
• 作为产物：
  描述：

  [4-Phenylmethoxy-1-(1,4,5-trimethoxynaphthalen-2-yl)butan-2-yl] acetate 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 9.0h， 生成 5,9,10-trimethoxy-3-(2-phenylmethoxyethyl)-3,4-dihydro-1H-benzo[g]isochromene
  参考文献：
  名称：

  Stereoselective, Oxidative C−C Bond Coupling of Naphthopyran Induced by DDQ:  Stereocontrolled Total Synthesis of Deoxyfrenolicin

  摘要：

  A formal total synthesis of pyranonaphthoquinone natural product deoxyfrenolicin 1 is described. The key step in the synthesis involves the use of stereoselective 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-induced C-C bond coupling of the naphthopyran 10 with allyltriphenyltin to give exclusively 1,3 trans naphthopyran derivative 23, The naphthopyran 10 was obtained via oxa-Pictet-Spengler cyclization of substituted naphthalene 22, which was derived by regioselective benzannulation of chromium carbene complex 12 with acetylene 18, This newly developed synthetic route employing a tandem benzannulation/oxa-Pictet-Spengler cyclization/DDQ-induced coupling strategy should also be applicable to the synthesis of other pyranonaphthoquinone natural products such as kalafungin 4 and nanaomycin 5.

  DOI：

  10.1021/ol9909738

文献信息

• Stereoselective, Oxidative C−C Bond Coupling of Naphthopyran Induced by DDQ:  Stereocontrolled Total Synthesis of Deoxyfrenolicin
  作者：Yao-Chang Xu、Dan T. Kohlman、Sidney X. Liang、Chad Erikkson

  DOI：10.1021/ol9909738

  日期：1999.11.1

  A formal total synthesis of pyranonaphthoquinone natural product deoxyfrenolicin 1 is described. The key step in the synthesis involves the use of stereoselective 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-induced C-C bond coupling of the naphthopyran 10 with allyltriphenyltin to give exclusively 1,3 trans naphthopyran derivative 23, The naphthopyran 10 was obtained via oxa-Pictet-Spengler cyclization of substituted naphthalene 22, which was derived by regioselective benzannulation of chromium carbene complex 12 with acetylene 18, This newly developed synthetic route employing a tandem benzannulation/oxa-Pictet-Spengler cyclization/DDQ-induced coupling strategy should also be applicable to the synthesis of other pyranonaphthoquinone natural products such as kalafungin 4 and nanaomycin 5.