3-苯基-1-萘甲酸甲酯 | 1033204-01-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-苯基-1-萘甲酸甲酯
• 英文名称: 3-phenyl-1-naphthalene carboxylic acid methyl ester
• 英文别名: 3-phenyl-naphthalene-1-carboxylic acid methyl ester；Methyl 3-phenylnaphthalene-1-carboxylate；methyl 3-phenylnaphthalene-1-carboxylate
• CAS: 1033204-01-1
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: UIWVJPYWPIHFPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴萘-1-羧酸甲酯 、 苯硼酸频哪醇酯 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90%的产率得到3-苯基-1-萘甲酸甲酯
  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

• Regioselective palladium-catalyzed ring-opening reactions of C₁-substituted oxabenzonorbornadienes
  作者：Mohammed Abdul Raheem、Michael Edmunds、William Tam

  DOI：10.1139/cjc-2014-0217

  日期：2014.9

  The effect of ethyl and methoxycarbonyl substitution on the C₁ position of oxabenzonorbornadienes undergoing palladium-catalyzed nucleophilic ring opening was investigated with a variety of aryl iodide nucleophiles. Electron-withdrawing groups in the C₁ position or on the aryl iodide afforded lower yields and led to aromatization of products. The presence of an electron-donating group in either position provided high yields in all cases. Despite variances in electronic nature, all trials produced a single regioisomeric product resulting from addition of the aryl group to the olefin carbon farthest from the C₁ substituent. Based on these findings, a mechanism has also been proposed.

  对氧苯并[2.2.1]辛二烯在钯催化的亲核开环反应中进行乙基和甲氧羰基取代对C₁位置的影响进行了研究，使用各种芳基碘亲核试剂。C₁位置或芳基碘中的电子吸引基团导致产率降低并使产物芳构化。在任一位置存在电子给予基团均提供高产率。尽管电子性质有所不同，所有实验均产生了一个单一的区域异构产物，该产物是芳基与离C₁取代基最远的烯烃碳的加成结果。基于这些发现，还提出了一个机理。
• 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.