6-(tert-butyl)-4,8-dimethylazulene | 13347-57-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 6-(tert-butyl)-4,8-dimethylazulene
• 英文别名: 6-t-butyl-4,8-dimethylazulene；6-tert-butyl-4,8-dimethyl-azulene；6-tert-Butyl-4,8-dimethyl-azulen；4.8-Dimethyl-6-tert-butyl-azulen；6-Tert.-butyl-4,8-dimethylazulene；6-tert-butyl-4,8-dimethylazulene
• CAS: 13347-57-4
• 化学式: C₁₆H₂₀
• 分子量: 212.335
• InChiKey: OTVQGUCHBOCKBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6-(tert-butyl)-4,8-dimethylazulene 在 sodium tetrahydroborate 、 正丁基锂 、 二异丙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 6-(tert-butyl)-1,8-dimethyl-4-[(methylthio)methyl]azulene
  参考文献：
  名称：

  Synthesis of 6-Styrylheptalenes

  摘要：

  4-Methylazulenes 3, 15, and 23 were transformed into 4-[(methylthio)methyl]azulene 4, and azulene-4-carbaldehyde dimethyl dithioacetals 16 and 24, respectively. Vilsmeier formylation of 4 and 16, and subsequent reduction led to the I-methyl derivatives 6 and 18, respectively. The thermal reaction of azulenes 6, 18, and 24 with dimethyl acetylenedicarboxylate (ADM) in toluene afforded heptalenes with a (methylthio)methyl group or a [bis(methylthio)]methyl group at C(6). Chlorination of [(methylthio)methyl]heptalene 7, followed by treatment with HgO and BF3. OEt2 in aqueous tetrahydrofuran (THF), led to 6-formylheptalene-dicarboxylate 12 in excellent yield. Similarly. hydrolysis of 18 and 24 by HgO and BF3. OEt2 in aqueous THF afforded the 6-formyl derivatives 21 and 27, respectively. Wittig reaction of the 6-formyl-substituted heptalenes and phosphonium salts 13a-e in the two-phase system CH2CI2/2N aqueous NaOH resulted in the formation of 6-styryl-substituted heptalenes.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1690::aid-hlca1690>3.0.co;2-d
• 作为产物：
  描述：

  2,6-二甲基-4-吡喃酮 在 四氢呋喃 、 高氯酸 、 乙醚 、 苯甲醚 作用下， 生成 6-(tert-butyl)-4,8-dimethylazulene
  参考文献：
  名称：

  Hafner; Kaiser, Justus Liebigs Annalen der Chemie, 1958, vol. 618, p. 140,148

  摘要：

  DOI：

文献信息

• 1-Phenylselanylazulenes: synthesis and selenium atom oxidation
  作者：Alexandru C. Razus、Liviu Birzan、Anamaria Hanganu、Mihaela Cristea、Eleonora-Mihaela Ungureanu、Maria-Laura Soare、George-Octavian Buica

  DOI：10.1007/s00706-014-1297-3

  日期：2014.12

  phenylselanylation of azulene with PhSeCl or PhSeBr was reported. Clean electrophilic substitution of azulene in positions 1 and/or 3 occurred with the first reagent whereas with PhSeBr a complex mixture of products was generated suggesting a radicalic mechanism. The influence on the reaction route of the substituent attached at position 1 of azulene, or of the alkyl positions in alkylated azulenes was investigated

  摘要据报道，用PhSeCl或PhSeBr将z烯的苯基硒基化。第一种和第二种试剂在位置1和/或3上进行了纯净的亲电取代，而用PhSeBr生成了复杂的产物混合物，表明存在自由基机理。研究了连接在a基1位上的取代基或烷基化的zu烯中烷基位置对反应路线的影响。使用偏高碘酸钠氧化1-苯基杂戊基氮杂烯和1,3-双（苯基杂戊基）氮杂。氧化发生在硒原子上，得到被PhSe（O）和/或PhSe（O 2）取代的天青烯）在位置1和/或3的基团上进行了记录。记录了所得产物的磁谱和电子谱以及电化学氧化和还原电势，并简要讨论了结果。 图形概要 。
• An Improved and Simplified Synthesis of 4-Styrylazulenes
  作者：Jianfeng Song、Hans-Jürgen Hansen

  DOI：10.1002/(sici)1522-2675(19990310)82:3<309::aid-hlca309>3.0.co;2-h

  日期：1999.3.10
• Synthesis of 6-Styrylheptalenes
  作者：Jianfeng Song、Hans-Jürgen Hansen

  DOI：10.1002/(sici)1522-2675(19991006)82:10<1690::aid-hlca1690>3.0.co;2-d

  日期：1999.10.6

  4-Methylazulenes 3, 15, and 23 were transformed into 4-[(methylthio)methyl]azulene 4, and azulene-4-carbaldehyde dimethyl dithioacetals 16 and 24, respectively. Vilsmeier formylation of 4 and 16, and subsequent reduction led to the I-methyl derivatives 6 and 18, respectively. The thermal reaction of azulenes 6, 18, and 24 with dimethyl acetylenedicarboxylate (ADM) in toluene afforded heptalenes with a (methylthio)methyl group or a [bis(methylthio)]methyl group at C(6). Chlorination of [(methylthio)methyl]heptalene 7, followed by treatment with HgO and BF3. OEt2 in aqueous tetrahydrofuran (THF), led to 6-formylheptalene-dicarboxylate 12 in excellent yield. Similarly. hydrolysis of 18 and 24 by HgO and BF3. OEt2 in aqueous THF afforded the 6-formyl derivatives 21 and 27, respectively. Wittig reaction of the 6-formyl-substituted heptalenes and phosphonium salts 13a-e in the two-phase system CH2CI2/2N aqueous NaOH resulted in the formation of 6-styryl-substituted heptalenes.
• Hafner; Kaiser, Justus Liebigs Annalen der Chemie, 1958, vol. 618, p. 140,148
  作者：Hafner、Kaiser

  DOI：——

  日期：——