methyl 2-(4-methylphenethyl)benzoate | 321534-83-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 2-(4-methylphenethyl)benzoate
• 英文别名: Methyl 2-[2-(4-methylphenyl)ethyl]benzoate
• CAS: 321534-83-2
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: ODENBCGUUYTWDP-UHFFFAOYSA-N

物化性质

• 沸点：
  362.8±21.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-methylphenethyl)benzoate 在 吡啶 、 sodium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 N-(4-Amino-2-methyl-quinolin-6-yl)-2-(2-p-tolyl-ethyl)-benzamide
  参考文献：
  名称：

  4-Aminoquinolines:  Novel Nociceptin Antagonists with Analgesic Activity

  摘要：

  Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure-activity relationships eventually led to the optimum compounds. One of the se compounds, N-(4-amino-2-methylquinolin-6-yl) -2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from mu -opioid agonists.

  DOI：

  10.1021/jm0002073
• 作为产物：
  描述：

  2-(三氟甲基磺酰氧基)苯甲酸甲酯 在 copper(l) iodide 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 四丁基碘化铵 、 三乙胺 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 37.0h， 生成 methyl 2-(4-methylphenethyl)benzoate
  参考文献：
  名称：

  Rapid Access to 3-Aryltetralin Skeleton via C(sp³)–H Bond Functionalization: Investigation on the Substituent Effect of Aromatic Ring Adjacent to C–H Bond in Hydride Shift/Cyclization Sequence

  摘要：

  通过氢转移介导的C–H键功能化成功构建了3-芳基四氢萘骨架。在这个过程中，苯基的[1,5]-氢转移顺利发生，生成了良好到优异化学产率的四氢萘衍生物。与C–H键相邻的芳香环的电子和立体性质显著影响了该转变的反应性。

  DOI：

  10.1246/cl.2011.1386

文献信息

• Concise Route to 3-Arylisoquinoline Skeleton by Lewis Acid Catalyzed C(sp³)–H Bond Functionalization and Its Application to Formal Synthesis of (±)-Tetrahydropalmatine
  作者：Keiji Mori、Taro Kawasaki、Takahiko Akiyama

  DOI：10.1021/ol300180w

  日期：2012.3.16

  An expeditious route to furnish an isoquinoline skeleton via hydride shift mediated C-H bond functionalization was developed. In this process, an unusual [1,5]-H shift without the assistance of the adjacent heteroatom took place to produce tetrahydroisoquinoline derivatives in good to excellent chemical yields. The formal synthesis of (+/-)-tetrahydropalmatine was achieved by exploiting this new transformation.