elisabatin B | 237749-85-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: elisabatin B
• 英文别名: 1H-Phenalen-1-one, 2-hydroxy-3,6,9-trimethyl-4-(2-methyl-1-propenyl)-；2-hydroxy-3,6,9-trimethyl-4-(2-methylprop-1-enyl)phenalen-1-one
• CAS: 237749-85-8
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: QPEDAMHNYYMCLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  pseudopterosin Y aglycone 在 盐酸羟胺 、 溶剂黄146 作用下， 反应 15.0h， 生成 elisabatin B
  参考文献：
  名称：

  Rapid structural diversification of pseudopterosins: sulfuric acid promoted dehydro-aromatization yielding 14,15-dihydro-elisabatin B

  摘要：

  Herein, we report a one-pot, sulfuric acid promoted, dehydro-aromatization reaction to rapidly convert pseudopterosins into 14,15-dihydro-elisabatin B. We propose a mechanism invoking redox cycling between the substrate catechol and ortho-quinone moieties. We also provide full spectroscopic characterization of two novel 5,6-dihydro-1H-phenalen-2(4H)-one derivatives, which are minor products of the reaction. This work opens up a unique route to rapidly provide libraries of novel marine natural product derivatives for drug discovery. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.03.013

文献信息

• Structurally Diverse Terpenoids from the Sea Whip Pseudopterogorgia elisabethae (Bayer)
  作者：A Rodríguez

  DOI：10.1016/s0040-4020(00)00754-7

  日期：2000.11.10

  The extraction of a specimen of Pseudopterogorgia elisabethae from Colombia afforded three new diterpenes 1-3, a norditerpene 4, and a tetrisnorditerpene 5. Metabolites 4 and 5 contain unusual carbon skeletons that are previously undescribed and therefore constitute new classes of C-19 and C-16 rearranged terpenes, respectively. Full details of the isolation and structure elucidation of 1-5, which were established by spectroscopic methods including comprehensive 2D NMR measurements, are provided herein. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Rapid structural diversification of pseudopterosins: sulfuric acid promoted dehydro-aromatization yielding 14,15-dihydro-elisabatin B
  作者：Malcolm W.B. McCulloch、Russell G. Kerr

  DOI：10.1016/j.tetlet.2015.03.013

  日期：2015.4

  Herein, we report a one-pot, sulfuric acid promoted, dehydro-aromatization reaction to rapidly convert pseudopterosins into 14,15-dihydro-elisabatin B. We propose a mechanism invoking redox cycling between the substrate catechol and ortho-quinone moieties. We also provide full spectroscopic characterization of two novel 5,6-dihydro-1H-phenalen-2(4H)-one derivatives, which are minor products of the reaction. This work opens up a unique route to rapidly provide libraries of novel marine natural product derivatives for drug discovery. (C) 2015 Elsevier Ltd. All rights reserved.