ethyl α-formyl-4-fluorophenylacetate | 104920-79-8

• 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 α-formyl-4-fluorophenylacetate
• 英文别名: ethyl 2-(4-fluorophenyl)-3-oxopropanoate；Ethyl 2-(4-fluorophenyl)-3-oxopropanoate
• CAS: 104920-79-8
• 化学式: C₁₁H₁₁FO₃
• 分子量: 210.205
• InChiKey: XYXSXSSTNGMQFV-UHFFFAOYSA-N

物化性质

• 沸点：
  280.9±30.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl α-formyl-4-fluorophenylacetate 在 吡啶 、 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 0
  参考文献：
  名称：

  Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones

  摘要：

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.047
• 作为产物：
  描述：

  甲酸乙酯 、 对氟苯乙酸乙酯 在 sodium 作用下， 以 甲苯 为溶剂， 反应 17.5h， 以68.2%的产率得到ethyl α-formyl-4-fluorophenylacetate
  参考文献：
  名称：

  α-取代芳基乙酸酯衍生物的合成及生物活性研究

  摘要：

  从山药中分离出山iso碱，用于治疗胃肠道平滑肌痉挛，感染性中毒性休克和有机磷中毒。但是没有关于山an碱具有α-葡糖苷酶抑制活性的报道。为了找到新颖的α-葡萄糖苷酶抑制剂，已经基于山an胺的活性单元合成了一系列α-取代的芳基乙酸酯衍生物。在α-葡萄糖苷酶测定中，席夫碱形式的化合物9和酯形式的化合物22显示出对α-葡萄糖苷酶的强烈抑制作用，IC 50值分别为46.81μM和83.76μM。化合物9和22表现出与市售药物格列美脲相当的良好的抗糖尿病活性。另外，α-取代的芳基乙酸酯的席夫碱显示出对人癌细胞系的抗肿瘤活性，其中具有硫脲部分的化合物9表现出最佳的抗肿瘤活性。我们预计我们的研究将为抗糖尿病药物设计提供潜在的候选支架。

  DOI：

  10.1016/j.bmcl.2016.02.055

文献信息

• Lewis Base Catalyzed Asymmetric Hydrosilylation of α-Substituted β-Enamino Esters: Facile Access to Enantioenriched β2-Amino Esters via Dynamic Kinetic Resolution
  作者：Xiao-Mei Zhang、Chang Shu、Xiao-Yan Hu、Shuai-Shuai Li、Wei-Cheng Yuan

  DOI：10.1055/s-0034-1378323

  日期：——

  A chiral Lewis base organocatalyzed asymmetric hydrosilylation of α-substituted β-enamino esters is presented. The reactions proceeded through dynamic kinetic resolution to afford various enantioenriched β2-amino esters with high yields (up to 98%) in moderate enantioselectivities (up to 77% ee).

  介绍了手性路易斯碱有机催化的 α-取代 β-烯氨基酯的不对称氢化硅烷化。反应通过动态动力学拆分进行，以中等对映选择性（高达 77% ee）以高产率（高达 98%）提供各种富含对映体的 β2-氨基酯。
• Discovery of isoxazolinone antibacterial agents. Nitrogen as a replacement for the stereogenic center found in oxazolidinone antibacterials
  作者：Lawrence B. Snyder、Zhaoxing Meng、Robert Mate、Stanley V. D’Andrea、Anne Marinier、Claude A. Quesnelle、Patrice Gill、Kenneth L. DenBleyker、Joan C. Fung-Tomc、MaryBeth Frosco、Alain Martel、John F. Barrett、Joanne J. Bronson

  DOI：10.1016/j.bmcl.2004.06.076

  日期：2004.9

  A series of potential antimicrobial derivatives possessing bioisosteric replacements for the central oxazolidinone ring found in oxazolidinone antibacterials have been prepared. The design concept involved replacement of the requisite SP3-hybridized stereogenic center found at the 5-position of the oxazolidinone with a nitrogen atom. The synthesis and antibacterial activity of three such ring systems, the benzisoxazolinones, pyrroles, and isoxazolinones is described. (C) 2004 Elsevier Ltd. All rights reserved.
• da Settimo; Primofiore; Ferrarini, Farmaco, Edizione Scientifica, 1986, vol. 41, # 8, p. 577 - 585
  作者：da Settimo、Primofiore、Ferrarini、Mori、Martini、Pennacchi、Lucacchini

  DOI：——

  日期：——
• Study on the synthesis and biological activities of α-substituted arylacetates derivatives
  作者：Jinbing Liu、Changhong Chen、Fengyan Wu、Junyuan Tang

  DOI：10.1016/j.bmcl.2016.02.055

  日期：2016.4

  α-glucosidase with IC50 value of 46.81 μM and 83.76 μM, respectively. Compounds 9 and 22 exhibit comparable good antidiabetic activities as commercial drug Glimepiride. In addition, Schiff bases of α-substituted arylacetates show antitumor activities against human cancer cell lines, where compound 9 with thiourea moiety performs the best antitumor activity. We anticipate that our research will provide potential

  从山药中分离出山iso碱，用于治疗胃肠道平滑肌痉挛，感染性中毒性休克和有机磷中毒。但是没有关于山an碱具有α-葡糖苷酶抑制活性的报道。为了找到新颖的α-葡萄糖苷酶抑制剂，已经基于山an胺的活性单元合成了一系列α-取代的芳基乙酸酯衍生物。在α-葡萄糖苷酶测定中，席夫碱形式的化合物9和酯形式的化合物22显示出对α-葡萄糖苷酶的强烈抑制作用，IC 50值分别为46.81μM和83.76μM。化合物9和22表现出与市售药物格列美脲相当的良好的抗糖尿病活性。另外，α-取代的芳基乙酸酯的席夫碱显示出对人癌细胞系的抗肿瘤活性，其中具有硫脲部分的化合物9表现出最佳的抗肿瘤活性。我们预计我们的研究将为抗糖尿病药物设计提供潜在的候选支架。
• Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones
  作者：Santosh Rajput、Christopher R. Gardner、Timothy W. Failes、Greg M. Arndt、David StC. Black、Naresh Kumar

  DOI：10.1016/j.bmc.2013.11.047

  日期：2014.1

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.