dimethyl 8-(tert-butyl)-6-formyl-1,10-dimethylheptalene-4,5-dicarboxylate | 253778-43-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 8-(tert-butyl)-6-formyl-1,10-dimethylheptalene-4,5-dicarboxylate
• 英文别名: Dimethyl 8-tert-butyl-10-formyl-5,6-dimethylheptalene-1,2-dicarboxylate
• CAS: 253778-43-7
• 化学式: C₂₃H₂₆O₅
• 分子量: 382.456
• InChiKey: MXVRKBDRXWLGGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 8-(tert-butyl)-6-formyl-1,10-dimethylheptalene-4,5-dicarboxylate 在 chromium dichloride 、 palladium diacetate 、 silver carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 dimethyl 8-(tert-butyl)-1,10-dimethyl-6-[(E,E)-4-phenylbuta-1,3-dienyl]heptalene-4,5-dicarboxylate
  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：

  6-(tert-butyl)-4,8-dimethylazulene 在 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 正丁基锂 、 三氟化硼乙醚 、 二异丙胺 、 三氟乙酸 、 mercury(II) oxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 37.0h， 生成 dimethyl 8-(tert-butyl)-6-formyl-1,10-dimethylheptalene-4,5-dicarboxylate
  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

文献信息

• 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.