4,10-bis(hexyloxy)-1,2,3,6b,7,8,9,12b-octahydroperylene | 1429325-82-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 4,10-bis(hexyloxy)-1,2,3,6b,7,8,9,12b-octahydroperylene
• 英文别名: 4,10-Dihexoxy-1,2,3,6b,7,8,9,12b-octahydroperylene；4,10-dihexoxy-1,2,3,6b,7,8,9,12b-octahydroperylene
• CAS: 1429325-82-5
• 化学式: C₃₂H₄₄O₂
• 分子量: 460.7
• InChiKey: TWFGHLYCXMJUNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-羟基-1-四氢萘酮 在 sodium tetrahydroborate 、 hafnium tetrakis(trifluoromethanesulfonate) 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 、 乙腈 为溶剂， 反应 28.17h， 生成 4,10-bis(hexyloxy)-1,2,3,6b,7,8,9,12b-octahydroperylene
  参考文献：
  名称：

  Synthesis of the altertoxin III framework

  摘要：

  The framework of altertoxin III, a mycotoxin produced by Alternaria fungi investing food and feed, has been synthesised for the first time. Synthetic schemes including Diels-Alder reactions of anthracene derivatives turned out to be not successful due to an aromatisation of key intermediates. This aromatisation was further investigated by DFT calculations, which showed that the aromatisation tendency is dependant from the electronic characteristics of attached substituents. A Friedel-Crafts-type hafnium triflate-catalysed dimerisation of dihydroxytetralins with subsequent benzylic oxidation furnished the target compound, which should be a suitable precursor for the synthesis of altertoxin III and related natural products. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.013

文献信息

• Synthesis of the altertoxin III framework
  作者：Oliver Geiseler、Monika Müller、Joachim Podlech

  DOI：10.1016/j.tet.2013.03.013

  日期：2013.5

  The framework of altertoxin III, a mycotoxin produced by Alternaria fungi investing food and feed, has been synthesised for the first time. Synthetic schemes including Diels-Alder reactions of anthracene derivatives turned out to be not successful due to an aromatisation of key intermediates. This aromatisation was further investigated by DFT calculations, which showed that the aromatisation tendency is dependant from the electronic characteristics of attached substituents. A Friedel-Crafts-type hafnium triflate-catalysed dimerisation of dihydroxytetralins with subsequent benzylic oxidation furnished the target compound, which should be a suitable precursor for the synthesis of altertoxin III and related natural products. (C) 2013 Elsevier Ltd. All rights reserved.