5-(hexyloxy)-3,4-dihydronaphthalen-1(2H)-one | 1429325-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-(hexyloxy)-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 5-hexoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 1429325-80-3
• 化学式: C₁₆H₂₂O₂
• mdl: MFCD21530241
• 分子量: 246.349
• InChiKey: RYSSKKMXTGOKGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.562
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(hexyloxy)-3,4-dihydronaphthalen-1(2H)-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以92%的产率得到5-hexyloxy-1,2,3,4-tetrahydronaphthalen-1-ol
  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
• 作为产物：
  描述：

  1,5-二羟基萘 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 sodium hydroxide 作用下， 以 水 、 异丙醇 、 丙酮 为溶剂， 70.0~80.0 ℃ 、600.01 kPa 条件下， 反应 21.5h， 生成 5-(hexyloxy)-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Altertoxin I 框架的合成

  摘要：

  苝醌衍生的霉菌毒素 I 的核心是由 3-羟基苯乙酮或 1,5-二羟基萘合成的，其中 Suzuki 偶联、Ullmann 偶联、McMurry 烯化和 Friedel-Crafts 乙酰化是各自合成中的关键步骤。

  DOI：

  10.1002/ejoc.202301052

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.
• Synthesis of the Altertoxin I Framework
  作者：Maximilian Gutsche、Dominik Pfaff、Joachim Podlech

  DOI：10.1002/ejoc.202301052

  日期：2024.1.15

  The core of the perylenequinone-derived mycotoxin altertoxin I was synthesized either from 3-hydroxyacetophenone or from 1,5-dihydroxynaphthalene, where Suzuki couplings, Ullmann couplings, McMurry olefinations, and Friedel-Crafts acetylation were key steps in the respective syntheses.

  苝醌衍生的霉菌毒素 I 的核心是由 3-羟基苯乙酮或 1,5-二羟基萘合成的，其中 Suzuki 偶联、Ullmann 偶联、McMurry 烯化和 Friedel-Crafts 乙酰化是各自合成中的关键步骤。