Prehalenaquinone | 158786-75-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Prehalenaquinone
• 英文别名: (1S,16S,17S)-17-hydroxy-1-methyl-14-oxapentacyclo[11.6.1.02,11.04,9.016,20]icosa-2(11),3,6,9,13(20)-pentaene-5,8,12-trione
• CAS: 158786-75-5
• 化学式: C₂₀H₁₆O₅
• 分子量: 336.344
• InChiKey: MYMGNUKZCJPHIG-APXLUKDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Prehalenaquinone 在 sodium dithionite 作用下， 以 丙酮 为溶剂， 反应 0.75h， 以100%的产率得到Prehalenaquinol
  参考文献：
  名称：

  Total Synthesis, Absolute Configuration, and Later Isolation of (-)-Prehalenaquinone, a Putative Biosynthetic Precursor to the Marine Natural Products: Halenaquinone and Xestoquinone

  摘要：

  As part of the total syntheses of halenaquinone (1) and xestoquinone (4), cardiotonic and cytotoxic marine natural products isolated from tropical marine sponges, we have found a new reaction pathway of the DMSO/DCC/PPTS or PTFA reagent that is useful for constructing a dihydrofuran ring system. By application of the reaction, we prepared synthetic intermediate (3S,3aS,12bS)-(-)-8 with a dihydrofuran ring moiety, from which both (+)-halenaquinone (1) and (+)-xestoquinone (4) were synthesized; DMSO/DCC/PPTS oxidation of dihydrofuran-alcohol 8 led to 1, while acid-catalyzed dehydration led to 4. The mechanism of the new DMSO/DCC/PPTS or PTFA reaction was clarified by use of O-18 labeling. We postulated that these synthetic routes might simulate the biosyntheses of 1 and 4 in marine sponges, and putative biosynthetic precursor (3S,3aS,12bS)-(-)-7, named prehalenaquinone, was synthesized. Later, we succeeded in isolating (-)-7 from an Okinawan marine sponge, Xestospongia sapra.

  DOI：

  10.1021/jo00101a019
• 作为产物：
  描述：

  (3S,4S,12bS)-1,2,3,4-tetrahydro-3,5-dihydroxy-4-(hydroxymethyl)-8,11-dimethoxy-12b-methyl-6(12bH)-benzoanthracenone 在 ammonium cerium(IV) nitrate 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 2.58h， 生成 Prehalenaquinone
  参考文献：
  名称：

  Total Synthesis, Absolute Configuration, and Later Isolation of (-)-Prehalenaquinone, a Putative Biosynthetic Precursor to the Marine Natural Products: Halenaquinone and Xestoquinone

  摘要：

  As part of the total syntheses of halenaquinone (1) and xestoquinone (4), cardiotonic and cytotoxic marine natural products isolated from tropical marine sponges, we have found a new reaction pathway of the DMSO/DCC/PPTS or PTFA reagent that is useful for constructing a dihydrofuran ring system. By application of the reaction, we prepared synthetic intermediate (3S,3aS,12bS)-(-)-8 with a dihydrofuran ring moiety, from which both (+)-halenaquinone (1) and (+)-xestoquinone (4) were synthesized; DMSO/DCC/PPTS oxidation of dihydrofuran-alcohol 8 led to 1, while acid-catalyzed dehydration led to 4. The mechanism of the new DMSO/DCC/PPTS or PTFA reaction was clarified by use of O-18 labeling. We postulated that these synthetic routes might simulate the biosyntheses of 1 and 4 in marine sponges, and putative biosynthetic precursor (3S,3aS,12bS)-(-)-7, named prehalenaquinone, was synthesized. Later, we succeeded in isolating (-)-7 from an Okinawan marine sponge, Xestospongia sapra.

  DOI：

  10.1021/jo00101a019

文献信息

• Total Synthesis, Absolute Configuration, and Later Isolation of (-)-Prehalenaquinone, a Putative Biosynthetic Precursor to the Marine Natural Products: Halenaquinone and Xestoquinone
  作者：Nobuyuki Harada、Tatsuo Sugioka、Hisashi Uda、Takeo Kuriki、Motomasa Kobayashi、Isao Kitagawa

  DOI：10.1021/jo00101a019

  日期：1994.11

  As part of the total syntheses of halenaquinone (1) and xestoquinone (4), cardiotonic and cytotoxic marine natural products isolated from tropical marine sponges, we have found a new reaction pathway of the DMSO/DCC/PPTS or PTFA reagent that is useful for constructing a dihydrofuran ring system. By application of the reaction, we prepared synthetic intermediate (3S,3aS,12bS)-(-)-8 with a dihydrofuran ring moiety, from which both (+)-halenaquinone (1) and (+)-xestoquinone (4) were synthesized; DMSO/DCC/PPTS oxidation of dihydrofuran-alcohol 8 led to 1, while acid-catalyzed dehydration led to 4. The mechanism of the new DMSO/DCC/PPTS or PTFA reaction was clarified by use of O-18 labeling. We postulated that these synthetic routes might simulate the biosyntheses of 1 and 4 in marine sponges, and putative biosynthetic precursor (3S,3aS,12bS)-(-)-7, named prehalenaquinone, was synthesized. Later, we succeeded in isolating (-)-7 from an Okinawan marine sponge, Xestospongia sapra.