1-guaiazuloyl bromide | 150985-87-8

• 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: 1-guaiazuloyl bromide
• 英文别名: 3,8-Dimethyl-5-propan-2-ylazulene-1-carbonyl bromide
• CAS: 150985-87-8
• 化学式: C₁₆H₁₇BrO
• 分子量: 305.214
• InChiKey: VLCSMJBESZCXCD-UHFFFAOYSA-N

物化性质

• 沸点：
  407.5±24.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	bis(3,8-dimethyl-5-isopropyl-1-azulenyl) ketone	10487-58-8	C31H34O	422.61
  愈创奥	7-isopropyl-1,4-dimethyl-azulene	489-84-9	C15H18	198.308

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	ethyl 3,8-dimethyl-5-isopropylazulene-1-carboxylate	81920-91-4	C18H22O2	270.371
  ——	ethyl 3-formyl-5-isopropyl-8-methylazulene-1-carboxylate	174355-71-6	C18H20O3	284.355
  ——	1,4-dimethyl-3-(4-hydroxyl-1-carbophenoxy)-7-isopropylazulene	——	C22H22O3	334.415
  ——	1,4-dimethyl-3-(3-hydroxyl-1-carbophenoxy)-7-isopropylazulene	——	C22H22O3	334.415
  愈创奥	7-isopropyl-1,4-dimethyl-azulene	489-84-9	C15H18	198.308
  ——	1,4-dimethyl-3-(2-hydroxyl-1-carbophenoxy)-7-isopropylazulene	——	C22H22O3	334.415
  ——	1,4-dimethyl-3-(3-methyl-4-hydroxyl-1-carbophenoxy)-7-isopropylazulene	——	C23H24O3	348.442
  ——	1,4-dimethyl-3-(2-methyl-4-hydroxyl-1-carbophenoxy)-7-isopropylazulene	——	C23H24O3	348.442
  ——	1,4-dimethyl-3-(4-hydroxyl-3-tert-butyl-1-carbophenoxy)-7-isopropylazulene	——	C26H30O3	390.522
  ——	1,4-dimethyl-3-(2,3-dimethyl-4-hydroxyl-1-carbophenoxy)-7-isopropylazulene	——	C24H26O3	362.469

反应信息

• 作为反应物：
  描述：

  1-guaiazuloyl bromide 在 对甲苯磺酸 作用下， 反应 1.0h， 生成 愈创奥
  参考文献：
  名称：

  Acid-catalyzed ethanolysis of di-l-azulenyl ketones

  摘要：

  Substituted di-1-azulenyl ketones composed of 3,8-dimethyl-5-isopropyl-1-azulenyl and/or 4,6,8-trimethyl-1-azulenyl group were refluxed in ethanol in the presence of p-toluenesulfonic acid to give substituted azulenes and ethyl-1-carboxylates derived from the cleavage of either of C-CO bonds of di-1-azulenyl ketones. The facility and the product distributions of the ethanolysis were affected markedly by the substituents.

  DOI：

  10.1016/s0040-4039(00)73636-7
• 作为产物：
  描述：

  bis(3,8-dimethyl-5-isopropyl-1-azulenyl) ketone 在 对甲苯磺酸 作用下， 反应 0.17h， 生成 1-guaiazuloyl bromide
  参考文献：
  名称：

  Acid-catalyzed ethanolysis of di-l-azulenyl ketones

  摘要：

  Substituted di-1-azulenyl ketones composed of 3,8-dimethyl-5-isopropyl-1-azulenyl and/or 4,6,8-trimethyl-1-azulenyl group were refluxed in ethanol in the presence of p-toluenesulfonic acid to give substituted azulenes and ethyl-1-carboxylates derived from the cleavage of either of C-CO bonds of di-1-azulenyl ketones. The facility and the product distributions of the ethanolysis were affected markedly by the substituents.

  DOI：

  10.1016/s0040-4039(00)73636-7

文献信息

• Guaiazulene-based phenolic radical scavengers: synthesis, properties, and EPR studies of their reaction with oxygen-centred radicals
  作者：Emanuela Franchi、Giovanni Ingrosso、Fabio Marchetti、Calogero Pinzino

  DOI：10.1016/s0040-4020(03)00737-3

  日期：2003.6

  starting from guaiazulene. Compounds 4 react with oxygen-centred radicals exhibiting chromotropic behaviour. The radical scavenging power of these compounds was evaluated by different methods. Compounds 4 are less efficient than some of the most common radical scavengers but show quite selective behaviour towards different oxygen-centred radicals. A correlation is found between the antioxidant activity of

  从愈创木烯开始制备了各种带有愈创木烯部分的酚类衍生物4。化合物4与以氧为中心的自由基反应，表现出变色行为。这些化合物的自由基清除能力通过不同的方法进行了评估。化合物4的效率不如某些最常见的自由基清除剂，但对不同的以氧为中心的自由基表现出相当高的选择性。发现化合物4的抗氧化活性与相应的酚O-H键离解能之间存在相关性。EPR和DFT研究阐明了化合物4与以氧为中心的自由基反应的某些方面。
• Solvent effect in molecular recognition: Determining binding constants in different solvents following an extraction based protocol
  作者：Uday Maitra、Photon Rao、Kumar P. Vijay、R. Balasubramanian、Lizamma Mathew

  DOI：10.1016/s0040-4039(98)00463-8

  日期：1998.5

  Semi-rigid molecular tweezers 1, 3 and 4 bind picric acid with more than tenfold increment in tetrachloromethane as compared to chloroform.

  与氯仿相比，半刚性分子镊子1、3和4以在四氯甲烷中十倍以上的增量结合苦味酸。
• Highly Sensitive Colorimetric Detection and Facile Isolation of Diamagnetic Free Radical Adducts of Novel Chromotropic Nitrone Spin Trapping Agents Readily Derived from Guaiazulene
  作者：David A. Becker

  DOI：10.1021/ja952895z

  日期：1996.1.1
• Bile Acid-Derived Molecular Tweezers:  Study of Solvent Effects in Binding, and Determination of Thermodynamic Parameters by an Extraction-Based Protocol
  作者：Vijay Kumar Potluri、Uday Maitra

  DOI：10.1021/jo000704r

  日期：2000.11.1

  A family of bile acid-based molecular tweezers (1-3) were synthesized, and their binding affinities with picric acid in different solvents were evaluated using a simple extraction-based protocol. The binding affinities increased in nonpolar solvents. The size of the solvent molecule did not affect the binding constant. Thermodynamic parameters for the binding of picric acid in CCl4 were also determined by this method. Binding constants of these tweezers with trinitrofluorenone in CDCl3 were determined by NMR titration.
• Acid-catalyzed ethanolysis of di-l-azulenyl ketones
  作者：Masaki Saitoh、Keitaro Hashimoto、Tomoo Nakazawa、Yoshikazu Sugihara

  DOI：10.1016/s0040-4039(00)73636-7

  日期：1993.5

  Substituted di-1-azulenyl ketones composed of 3,8-dimethyl-5-isopropyl-1-azulenyl and/or 4,6,8-trimethyl-1-azulenyl group were refluxed in ethanol in the presence of p-toluenesulfonic acid to give substituted azulenes and ethyl-1-carboxylates derived from the cleavage of either of C-CO bonds of di-1-azulenyl ketones. The facility and the product distributions of the ethanolysis were affected markedly by the substituents.