3-(4-cyano-phenyl)-naphthalene-1-carboxylic acid methyl ester | 1033204-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(4-cyano-phenyl)-naphthalene-1-carboxylic acid methyl ester
• 英文别名: Methyl 3-(4-cyanophenyl)naphthalene-1-carboxylate；methyl 3-(4-cyanophenyl)naphthalene-1-carboxylate
• CAS: 1033204-03-3
• 化学式: C₁₉H₁₃NO₂
• 分子量: 287.318
• InChiKey: MERRUHZLWOJXFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴萘-1-羧酸甲酯 、 4-(4,4,5,5-四甲基-1,3,2-二恶硼)苯甲腈 在 palladium diacetate potassium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 0.12h， 以85%的产率得到3-(4-cyano-phenyl)-naphthalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Comparison of monomode and multimode microwave equipment in Suzuki–Miyaura reactions—en route to high throughput parallel synthesis under microwave conditions

  摘要：

  The microwave heated Suzuki-Miyaura cross-coupling reaction of boronic acids, boronic esters and organotrifluoroborates served as a model reaction in a singlemode equipment. The reaction conditions were optimized with respect to temperature and reaction time and were transferred to multimode equipment which is well suited for multiparallel synthesis in a larger scale. The source of the Pd species chosen included immobilized Pd complexes and Pd particles. In fact the increased time to reach the required reaction time in multimode chambers suitable for 48 parallel reactions has to be taken into account. The nature of the boronic acid has no impact on the efficiency of the catalytic process. However, heterogenized Pd species perform less well in multimode chambers with larger vial volumes, which we ascribe to diffusion phenomena. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.094

文献信息

• Comparison of monomode and multimode microwave equipment in Suzuki–Miyaura reactions—en route to high throughput parallel synthesis under microwave conditions
  作者：Uwe Schön、Josef Messinger、Simone Eichner、Andreas Kirschning

  DOI：10.1016/j.tetlet.2008.03.094

  日期：2008.5

  The microwave heated Suzuki-Miyaura cross-coupling reaction of boronic acids, boronic esters and organotrifluoroborates served as a model reaction in a singlemode equipment. The reaction conditions were optimized with respect to temperature and reaction time and were transferred to multimode equipment which is well suited for multiparallel synthesis in a larger scale. The source of the Pd species chosen included immobilized Pd complexes and Pd particles. In fact the increased time to reach the required reaction time in multimode chambers suitable for 48 parallel reactions has to be taken into account. The nature of the boronic acid has no impact on the efficiency of the catalytic process. However, heterogenized Pd species perform less well in multimode chambers with larger vial volumes, which we ascribe to diffusion phenomena. (c) 2008 Elsevier Ltd. All rights reserved.