12,12a-dihydro-1,7-dihydroxy-5a-methyl-5H-dibenzo[b,h]fluorene-5,6,11,13(5aH)-tetrone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 12,12a-dihydro-1,7-dihydroxy-5a-methyl-5H-dibenzo[b,h]fluorene-5,6,11,13(5aH)-tetrone
• 英文别名: (±)-zeylanone；(2R,11R)-8,19-dihydroxy-2-methylpentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(13),4(9),5,7,15(20),16,18-heptaene-3,10,14,21-tetrone
• 化学式: C₂₂H₁₄O₆
• 分子量: 374.35
• InChiKey: XVMQJJJRMHQCGD-AMXDTQDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  12,12a-dihydro-1,7-dihydroxy-5a-methyl-5H-dibenzo[b,h]fluorene-5,6,11,13(5aH)-tetrone 在 盐酸 、 水 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 50.5h， 生成 zeylanone
  参考文献：
  名称：

  Biomimetic Synthesis of Zeylanone and Zeylanone Epoxide by Dimerization of 2-Methyl-1,4-naphthoquinone

  摘要：

  A biomimetic synthesis of zeylanone and zeylanone epoxide, which are natural dimeric naphthoquinones, has been accomplished starting from plumbagin, a natural monomeric naphthoquinone. The key features of our synthesis are cascade intermolecular and intramolecular Michael reactions, followed by epoxidation of the resultant hydroquinone with molecular oxygen.

  DOI：

  10.1021/ol400335s
• 作为产物：
  描述：

  兰雪醌 在 氧气 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 paraffin oil 为溶剂， 反应 53.58h， 生成 12,12a-dihydro-1,7-dihydroxy-5a-methyl-5H-dibenzo[b,h]fluorene-5,6,11,13(5aH)-tetrone
  参考文献：
  名称：

  Biomimetic Synthesis of Zeylanone and Zeylanone Epoxide by Dimerization of 2-Methyl-1,4-naphthoquinone

  摘要：

  A biomimetic synthesis of zeylanone and zeylanone epoxide, which are natural dimeric naphthoquinones, has been accomplished starting from plumbagin, a natural monomeric naphthoquinone. The key features of our synthesis are cascade intermolecular and intramolecular Michael reactions, followed by epoxidation of the resultant hydroquinone with molecular oxygen.

  DOI：

  10.1021/ol400335s

文献信息

• Biomimetic Synthesis of Zeylanone and Zeylanone Epoxide by Dimerization of 2-Methyl-1,4-naphthoquinone
  作者：Sayako Maruo、Kazuyuki Nishio、Takahiro Sasamori、Norihiro Tokitoh、Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1021/ol400335s

  日期：2013.4.5

  A biomimetic synthesis of zeylanone and zeylanone epoxide, which are natural dimeric naphthoquinones, has been accomplished starting from plumbagin, a natural monomeric naphthoquinone. The key features of our synthesis are cascade intermolecular and intramolecular Michael reactions, followed by epoxidation of the resultant hydroquinone with molecular oxygen.