1-(3-guaiazulenylmethyl)-4-methoxybenzene

• 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: 1-(3-guaiazulenylmethyl)-4-methoxybenzene
• 英文别名: (3-guaiazulenyl)(4-methoxyphenyl)methane；3-[(4-Methoxyphenyl)methyl]-1,4-dimethyl-7-propan-2-ylazulene；3-[(4-methoxyphenyl)methyl]-1,4-dimethyl-7-propan-2-ylazulene
• 化学式: C₂₃H₂₆O
• 分子量: 318.459
• InChiKey: DFEDNHXDSKVNGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (3-guaiazulenyl)(4-methoxyphenyl)methylium hexafluorophosphate 在 sodium tetrahydroborate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.5h， 以95%的产率得到1-(3-guaiazulenylmethyl)-4-methoxybenzene
  参考文献：
  名称：

  An efficient preparation, crystal structures, and properties of monocarbenium-ion compounds stabilized by 3-guaiazulenyl and anisyl groups

  摘要：

  Reaction of guaiazulene (1) with 2-methoxybenzaldehyde (2) in methanol in the presence of hexafluorophosphoric acid at 25 degrees C for 2 h gives (3-guaiazulenyl)(2-methoxyphenyl) methylium hexafluorophosphate (5a) in 93% yield. Similarly, reaction of 1 with 3-methoxy-benzaldehyde (3) or 4-methoxybenzaldehyde (4) under the same reaction conditions as for 2 affords (3-guaiazulenyl)(3-methoxyphenyl) methylium hexafluorophosphate (6) (91% yield) or (3-guaiazulenyl)(4-methoxyphenyl) methylium hexafluorophosphate (7) (97% yield). The crystal structures as well as the spectroscopic, electrochemical, and chemical properties of these monocarbenium-ion compounds, possessing interesting resonance forms, stabilized by the 3-guaiazulenyl and anisyl (i.e., 2-, 3-, or 4-methoxyphenyl) groups are reported. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.001

文献信息

• Preparation and Characterization of Aryl or Heteroaryl(3-indolyl)methylium <i>o</i>-Benzenedisulfonimides
  作者：Margherita Barbero、Silvano Cadamuro、Fabrizio Cauda、Stefano Dughera、Giuliana Gervasio、Paolo Venturello

  DOI：10.1021/jo300099y

  日期：2012.5.4

  An initial study has been accomplished into the synthetic feasibility of the preparation of diarylcarbenium salt via the direct coupling of aryl (or heteroaryl) aldehydes and arenes (or heteroaryl analogues) in the presence of a strong organic Brønsted acid. A number of stabilized aryl or heteroaryl(3-indolyl)carbenium ions, never previously prepared in the solid state, have been isolated in excellent

  在强有机布朗斯台德酸的存在下，通过芳基（或杂芳基）醛与芳烃（或杂芳基类似物）的直接偶联，制备二芳基碳鎓盐的合成可行性已完成了初步研究。以前从未以固态形式制备过的许多稳定的芳基或杂芳基（3-吲哚基）碳鎓离子已经以极高的收率分离为高度稳定的邻苯二磺酰亚胺盐，并已得到充分表征。通过光谱方法和用NaBH 4进行化学还原已证明了其纯度。已对其中一种产品进行了X射线晶体结构分析：氮杂富烯鎓物种显示为固态的排他性结构。
• An efficient preparation, crystal structures, and properties of monocarbenium-ion compounds stabilized by 3-guaiazulenyl and anisyl groups
  作者：Shin-ichi Takekuma、Masayuki Tamura、Toshie Minematsu、Hideko Takekuma

  DOI：10.1016/j.tet.2007.09.001

  日期：2007.11

  Reaction of guaiazulene (1) with 2-methoxybenzaldehyde (2) in methanol in the presence of hexafluorophosphoric acid at 25 degrees C for 2 h gives (3-guaiazulenyl)(2-methoxyphenyl) methylium hexafluorophosphate (5a) in 93% yield. Similarly, reaction of 1 with 3-methoxy-benzaldehyde (3) or 4-methoxybenzaldehyde (4) under the same reaction conditions as for 2 affords (3-guaiazulenyl)(3-methoxyphenyl) methylium hexafluorophosphate (6) (91% yield) or (3-guaiazulenyl)(4-methoxyphenyl) methylium hexafluorophosphate (7) (97% yield). The crystal structures as well as the spectroscopic, electrochemical, and chemical properties of these monocarbenium-ion compounds, possessing interesting resonance forms, stabilized by the 3-guaiazulenyl and anisyl (i.e., 2-, 3-, or 4-methoxyphenyl) groups are reported. (C) 2007 Elsevier Ltd. All rights reserved.