methyl 2-(2-phenylethyl)benzoate | 194605-53-3

• 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-(2-phenylethyl)benzoate
• 英文别名: methyl 2-phenethylbenzoate；bibenzyl-2-carboxylic acid methyl ester；Bibenzyl-2-carbonsaeure-methylester
• CAS: 194605-53-3
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: IYHWVFNWCXRGBE-UHFFFAOYSA-N

物化性质

• 沸点：
  346.2±21.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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-(2-phenylethyl)benzoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以70%的产率得到2-苯乙基苯甲醇
  参考文献：
  名称：

  Carrara, Maria; Zampiron, Stefano; Pittarello, Demetrio, Arzneimittel-Forschung/Drug Research, 1997, vol. 47, # 7, p. 803 - 809

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-methyl 2-styrylbenzoate 在 5percent Pd/C 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、250.0 kPa 条件下， 反应 0.67h， 生成 methyl 2-(2-phenylethyl)benzoate
  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

文献信息

• One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp²–Sp³ Cross-Coupling
  作者：Takaoki Koyanagi、Ananda Herath、Ashley Chong、Maxim Ratnikov、Andrew Valiere、Jim Chang、Valentina Molteni、Jon Loren

  DOI：10.1021/acs.orglett.8b04090

  日期：2019.2.1

  been developed using redox-active esters prepared in situ from alkyl carboxylates and N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (PITU). This undivided cell one-pot method enables C–C bond formation using inexpensive, benchtop-stable reagents with isolated yields up to 95% with good functional group tolerance, which includes nitrile, ketone, ester, alkene and selectivity over other aromatic

  使用由烷基羧酸盐和N-羟基邻苯二甲酰亚胺四甲基脲六氟磷酸盐（PITU）原位制备的氧化还原活性酯，开发了一种一锅式电化学镍催化的脱羧sp 2 -sp 3交叉偶联反应 。这种无分隔的单元一锅法可使用廉价的台式稳定剂实现C-C键的形成，分离出的收率高达95％，具有良好的官能团耐受性，其中包括腈，酮，酯，烯烃和对其他芳香族卤素的选择性。
• Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold
  作者：Giulia Rotondi、Paolo Guglielmi、Simone Carradori、Daniela Secci、Celeste De Monte、Barbara De Filippis、Cristina Maccallini、Rosa Amoroso、Roberto Cirilli、Atilla Akdemir、Andrea Angeli、Claudiu T. Supuran

  DOI：10.1080/14756366.2019.1651315

  日期：2019.1.1

  Abstract A large library of derivatives based on the scaffold of 2-(benzylsulfinyl)benzoic acid were synthesised and tested as atypical inhibitors against four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). The exploration of the chemical space around the main functional groups led to the discovery of selective hCA IX inhibitors in the micromolar/nanomolar range

  抽象的 合成了大量基于2-（苄基亚磺酰基）苯甲酸支架的衍生物库，并作为针对人碳酸酐酶的四种不同同工型的非典型抑制剂进行了测试（hCA I，II，IX和XII，EC 4.2.1.1）。对主要官能团周围的化学空间的探索导致发现了微摩尔/纳摩尔范围内的选择性hCA IX抑制剂，从而在这种多功能支架内建立了稳固的结构-活性关系。进行了一些选定手性化合物的HPLC分离和相应对映异构体的生物学评估，并对活性最高的衍生物进行了分子建模研究。
• Modulators of melanocortin receptor
  申请人：Vos J. Tricia

  公开号：US20070293498A1

  公开（公告）日：2007-12-20

  This invention provides compounds and methods for treating melanocortin receptor associated disorders, such as weight loss disorders including cachexia resulting from cancer and other chronic illnesses. The compounds are represented by formula I: wherein X is oxygen or sulfur; G is G1 or G2: L 1 , L 2 , L 3 and Q are linker groups, and Rings A, B and C, and R 1 -R 14 are described in the specification. The compounds are antagonists of melanocortin receptors.

  本发明提供了化合物和方法，用于治疗黑色素皮质素受体相关疾病，如由癌症和其他慢性疾病引起的消瘦症等减重疾病。化合物由公式I表示：其中X是氧或硫；G是G1或G2：L1，L2，L3和Q是连接基，环A，B和C以及R1-R14在说明书中描述。化合物是黑色素皮质素受体的拮抗剂。
• 10.1039/d4gc03057e
  作者：Huang, Tao、Liu, Can、Yuan, Pan-Feng、Wang, Tao、Yang, Biao、Ma, Yao、Liu, Qiang

  DOI：10.1039/d4gc03057e

  日期：——

  The γ C–H amination of carboxylic acid presents a promising and sustainable strategy for synthesizing high-value pharmaceutical chemicals. Radical reaction pathways initiated by aroyloxy radical-involved hydrogen atom transfer (HAT) provide diverse but challenging opportunities for remote C–H functionalization. In this report, the first example of intramolecular γ C–H amination of carboxylic acids

  羧酸的γC-H胺化为合成高价值医药化学品提供了一种有前途且可持续的策略。由芳酰氧基参与的氢原子转移（HAT）引发的自由基反应途径为远程C-H官能化提供了多样化但具有挑战性的机会。在本报告中，实现了使用市售肟助剂对羧酸进行分子内 γ C-H 胺化的第一个例子。这种创新方法采用自由基中继分子伴侣，通过1,5-HAT/自由基交叉偶联促进选择性 C-H 官能化，并实现氨在羧酸的 γ 碳上的净结合。此外，该方案还可以回收副产物二苯甲酮，并且产物分离和副产物回收均无需硅胶。该反应具有高化学和区域选择性，在温和的反应条件下进行，具有广泛的底物范围，表现出良好的官能团兼容性，并且易于扩展。
• Schlenk; Bergmann, Justus Liebigs Annalen der Chemie, 1928, vol. 463, p. 208
  作者：Schlenk、Bergmann

  DOI：——

  日期：——