2,2',3',4'-tetramethoxydiphenyl-5-carbaldehyde | 283159-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2',3',4'-tetramethoxydiphenyl-5-carbaldehyde
• 英文别名: 4-Methoxy-3-(2,3,4-trimethoxyphenyl)benzaldehyde
• CAS: 283159-30-8
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: KXEODFKHCWQIKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2',3',4'-tetramethoxydiphenyl-5-carbaldehyde 在 氢氧化钾 、 三氟化硼乙醚 、 potassium iodide 三氯化铝 、 sodium cyanoborohydride 、 potassium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 硝基苯 、 丙酮 为溶剂， 反应 91.0h， 生成 4-benzyloxy-5-(4-cyanobutyl)-5'-(2-cyanoethyl)-2,2',3-trimethoxydiphenyl
  参考文献：
  名称：

  Isolation of Macrocyclic Metacyclophanes From the Attempted Synthesis of [7.0]Metacyclophanes of the Myricanone Series by Thorpe-Ziegler - Intramolecular Cyclization of Diaryls Substituted by ω-Cyanoalkyl Chains

  摘要：

  The syntheses of the diaryls 14 and 21, substituted by two omega-cyanoalkyl chains (one on each ring), are described. Treatment of the unsymmetrical diaryl 14 with NaN(Me)Ph in a Thorpe-Ziegler reaction failed to give any definite product. Under the same conditions the symmetrical diaryl 21 led to an isomeric mixture of dimeric enaminonitriles 24. Mild acidic hydrolysis of the latter yielded the isomeric beta-ketonitriles 25, whereas more drastic hydrolytic conditions led to the macrocyclic diketone 26.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1527::aid-ejoc1527>3.0.co;2-g
• 作为产物：
  描述：

  3-溴-4-甲氧基苯甲醛 、 2,3,4-三甲氧基苯硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 18.0h， 以98%的产率得到2,2',3',4'-tetramethoxydiphenyl-5-carbaldehyde
  参考文献：
  名称：

  Isolation of Macrocyclic Metacyclophanes From the Attempted Synthesis of [7.0]Metacyclophanes of the Myricanone Series by Thorpe-Ziegler - Intramolecular Cyclization of Diaryls Substituted by ω-Cyanoalkyl Chains

  摘要：

  The syntheses of the diaryls 14 and 21, substituted by two omega-cyanoalkyl chains (one on each ring), are described. Treatment of the unsymmetrical diaryl 14 with NaN(Me)Ph in a Thorpe-Ziegler reaction failed to give any definite product. Under the same conditions the symmetrical diaryl 21 led to an isomeric mixture of dimeric enaminonitriles 24. Mild acidic hydrolysis of the latter yielded the isomeric beta-ketonitriles 25, whereas more drastic hydrolytic conditions led to the macrocyclic diketone 26.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1527::aid-ejoc1527>3.0.co;2-g

文献信息

• Isolation of Macrocyclic Metacyclophanes From the Attempted Synthesis of [7.0]Metacyclophanes of the Myricanone Series by Thorpe-Ziegler - Intramolecular Cyclization of Diaryls Substituted by ω-Cyanoalkyl Chains
  作者：Bénédicte Dansou、Christophe Pichon、Robert Dhal、Eric Brown、Stéphane Mille

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1527::aid-ejoc1527>3.0.co;2-g

  日期：2000.4

  The syntheses of the diaryls 14 and 21, substituted by two omega-cyanoalkyl chains (one on each ring), are described. Treatment of the unsymmetrical diaryl 14 with NaN(Me)Ph in a Thorpe-Ziegler reaction failed to give any definite product. Under the same conditions the symmetrical diaryl 21 led to an isomeric mixture of dimeric enaminonitriles 24. Mild acidic hydrolysis of the latter yielded the isomeric beta-ketonitriles 25, whereas more drastic hydrolytic conditions led to the macrocyclic diketone 26.