4-Phenylmethoxy-1-(1,4,5-trimethoxynaphthalen-2-yl)butan-2-ol | 251938-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-Phenylmethoxy-1-(1,4,5-trimethoxynaphthalen-2-yl)butan-2-ol
• 英文别名: 4-phenylmethoxy-1-(1,4,5-trimethoxynaphthalen-2-yl)butan-2-ol
• CAS: 251938-83-7
• 化学式: C₂₄H₂₈O₅
• 分子量: 396.483
• InChiKey: HOVDSXDVKJPOSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Phenylmethoxy-1-(1,4,5-trimethoxynaphthalen-2-yl)butan-2-ol 在 palladium on activated charcoal chromium(VI) oxide 、 4 A molecular sieve 、 硫酸 、 三氟化硼乙醚 、 氢气 、 lithium perchlorate 、 三溴化硼 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 59.23h， 生成 trans-methyl <9-hydroxy-1-propyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-naphtho<2,3-c>pyran-3-yl>acetate
  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 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以85%的产率得到4-Phenylmethoxy-1-(1,4,5-trimethoxynaphthalen-2-yl)butan-2-ol
  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.