lanciaquinone | 638203-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: lanciaquinone
• 英文别名: 3-[14-(2,5-dihydroxy-3,6-dioxo-1,4-cyclohexadien-1-yl)tetradecyl]-2-hydroxy-5-methylbenzo-1,4-quinone；3-[14-(2,5-Dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-2-hydroxy-5-methylcyclohexa-2,5-diene-1,4-dione；3-[14-(2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tetradecyl]-2-hydroxy-5-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 638203-08-4
• 化学式: C₂₇H₃₆O₇
• 分子量: 472.579
• InChiKey: LUTCDQOQIHCTDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 lanciaquinone 在 吡啶 作用下， 反应 24.0h， 以63%的产率得到4-(acetyloxy)-2-{14-[2-(acetyloxy)-5-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl]tetradecyl}-3,6-dioxo-1,4-cyclohexadien-1-yl acetate
  参考文献：
  名称：

  Synthesis of the Reported Structure of the Bisbenzoquinone Lanciaquinone, Isolated from Maesa lanceolata

  摘要：

  Lanciaquinone, isolated from Maesa lanceolata, was originally assigned as a bisbenzoquinone with a C-14-chain linking the two quinone rings. A synthesis of the reported structure, in which the key step is a double Claisen rearrangement, suggests that the structure of the natural product needs to be revised.

  DOI：

  10.1021/ol801697g
• 作为产物：
  描述：

  3-[14-(3,6-Dioxo-2,5-bis{[2-(trimethylsilyl)ethoxy]methoxy}-1,4-cyclohexadien-1-yl)tetradecyl]-5-methyl-2-{[2-(trimethylsilyl)ethoxy]methoxy}benzo-1,4-quinone 在 六氟合硅酸 作用下， 以 乙腈 为溶剂， 以81%的产率得到lanciaquinone
  参考文献：
  名称：

  Synthesis of the Reported Structure of the Bisbenzoquinone Lanciaquinone, Isolated from Maesa lanceolata

  摘要：

  Lanciaquinone, isolated from Maesa lanceolata, was originally assigned as a bisbenzoquinone with a C-14-chain linking the two quinone rings. A synthesis of the reported structure, in which the key step is a double Claisen rearrangement, suggests that the structure of the natural product needs to be revised.

  DOI：

  10.1021/ol801697g

文献信息

• Benzoquinone derivatives of Myrsine africana and Maesa lanceolata
  作者：Lawrence O. Arot Manguro、Jacob O. Midiwo、Wolfgang Kraus、Ivar Ugi

  DOI：10.1016/s0031-9422(03)00428-x

  日期：2003.10

  The fruits of Myrsine africana afforded two new benzoquinone derivatives, methylvilangin and methylanhydrovilangin. On the other hand, from the fruits of Maesa lanceolata two more novel compounds; 2,5-dihydroxy-3-(nonadec-14-enyl)-benzoquinone and lanciaquinone were isolated. Their structural elucidation was achieved by spectroscopic measurements including 2D NMR experiments. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of the Reported Structure of the Bisbenzoquinone Lanciaquinone, Isolated from <i>Maesa lanceolata</i>
  作者：Loic Guillonneau、David Taddei、Christopher J. Moody

  DOI：10.1021/ol801697g

  日期：2008.10.16

  Lanciaquinone, isolated from Maesa lanceolata, was originally assigned as a bisbenzoquinone with a C-14-chain linking the two quinone rings. A synthesis of the reported structure, in which the key step is a double Claisen rearrangement, suggests that the structure of the natural product needs to be revised.