ethyl 2-(4-(benzylamino)phenyl)acetate | 57960-76-6

• 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: ethyl 2-(4-(benzylamino)phenyl)acetate
• 英文别名: ethyl 2-(4-benzylaminophenyl)acetate；4-benzilamminofenilacetato d'etile；ethyl 4-benzylaminophenylacetate；(4-benzylamino-phenyl)-acetic acid ethyl ester；(4-Benzylamino-phenyl)-essigsaeure-aethylester；Ethyl 2-[4-(benzylamino)phenyl]acetate
• CAS: 57960-76-6
• 化学式: C₁₇H₁₉NO₂
• mdl: MFCD03019351
• 分子量: 269.343
• InChiKey: STWRUFUDZZDORZ-UHFFFAOYSA-N

物化性质

• 沸点：
  401.0±33.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-(benzylamino)phenyl)acetate 在 盐酸 、 aluminum (III) chloride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 硝基苯 为溶剂， 反应 7.0h， 生成 吲哚布芬
  参考文献：
  名称：

  마이크로 플로우 리액터를 이용한 인도부펜의 제조방법

  摘要：

  本发明涉及一种以商业上可购买的商业上可购买的乙基2-(4-氨基苯基)乙酸乙酯为起始物质制备对乙酰氨基酚的方法以及将其应用于微流反应器的方法。根据本发明，通过使用微流反应器制备对乙酰氨基酚，可以提高对乙酰氨基酚的产率和纯度，缩短整个制造过程所需的时间，并可以安全地使用在制造过程中使用的有害化合物。

  公开号：

  KR101778331B1
• 作为产物：
  描述：

  (4-benzylidenamino-phenyl)-acetic acid ethyl ester 在 镍 、 乙酸乙酯 作用下， 生成 ethyl 2-(4-(benzylamino)phenyl)acetate
  参考文献：
  名称：

  Drefahl; Ulbricht, Justus Liebigs Annalen der Chemie, 1955, vol. 598, p. 174,183

  摘要：

  DOI：

文献信息

• Visible light-mediated oxidative decarboxylation of arylacetic acids into benzyl radicals: addition to electron-deficient alkenes by using photoredox catalysts
  作者：Yoshihiro Miyake、Kazunari Nakajima、Yoshiaki Nishibayashi

  DOI：10.1039/c3cc44438d

  日期：——

  arylacetic acids bearing an amino group at the para-position in the benzene ring with alkenes in the presence of a catalytic amount of transition metal polypyridyl complexes as photocatalysts under visible light illumination proceed smoothly to give the corresponding benzylated products via oxidative decarboxylation in good to high yields.

  在可见光照射下，在催化量的过渡金属聚吡啶基配合物作为光催化剂的存在下，苯环对位带有氨基的芳酸与烯烃的反应顺利进行，通过氧化脱羧得到相应的苄基化产物高产。
• Direct N-Alkylation of Aromatic Amines Using a Microflow Reactor: Enhancement of Selectivity and Reactivity
  作者：Jin-Hyun Jeong、Yong-Sung Choi、Yoon-Jung Kim、Liu-Lan Shen、Yong Lee

  DOI：10.1055/s-0034-1379895

  日期：——

  A simple and highly atom-economical method for the direct N-alkylation of aromatic amines by using a microflow reactor was developed to overcome the problem of over-alkylation. In the developed method, high-yield conversion (up to 100%) was achieved in a relatively short reaction time. The ratio of mono- to di-benzylated products (3.57:1) was higher than that achieved with batch reactions conducted in a 1L scale flask (0.87:1). The structural features of the microflow reactor meant that short-chain alkyl halides could be converted into products with high reactivity and selectivity under superheating conditions, although their boiling point was much lower than the reaction temperature. This method was successfully applied to the synthesis of a range of secondary amines including an intermediate of indobufen synthesis.
• Structural optimization and in vitro profiling of N-phenylbenzamide-based farnesoid X receptor antagonists
  作者：Jurema Schmidt、Simone Schierle、Leonie Gellrich、Astrid Kaiser、Daniel Merk

  DOI：10.1016/j.bmc.2018.07.017

  日期：2018.8

  Activation of the nuclear farnesoid X receptor (FXR) which acts as cellular bile acid sensor has been validated as therapeutic strategy to counter liver disorders such as non-alcoholic steatohepatitis by the clinical efficacy of obeticholic acid. FXR antagonism, in contrast, is less well studied and potent small molecule FXR antagonists are rare. Here we report the systematic optimization of a novel class of FXR antagonists towards low nanomolar potency. The most optimized compound antagonizes baseline and agonist induced FXR activity in a full length FXR reporter gene assay and represses intrinsic expression of FXR regulated genes in hepatoma cells. With this activity and a favorable toxicity-, stability- and selectivity-profile it appears suitable to further study FXR antagonism in vitro and in vivo.
• Picciola; Ravenna; Carenini, Farmaco, Edizione Scientifica, 1981, vol. 36, # 1, p. 47 - 60
  作者：Picciola、Ravenna、Carenini、Manzardo、Gentili

  DOI：——

  日期：——
• PICCIOLA G.; RAVENNA F.; CARENINI G.; MANZARDO S.; GENTILI P., FARMACO. ED. SCI., 1981, 36, NO 1, 47-60
  作者：PICCIOLA G.、 RAVENNA F.、 CARENINI G.、 MANZARDO S.、 GENTILI P.

  DOI：——

  日期：——