ethyl 2-(2-tert-butylanilino)-2-oxo-acetate | 959508-79-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(2-tert-butylanilino)-2-oxo-acetate
• 英文别名: Oxanilic acid, 2-tert-butyl-, ethyl ester；ethyl 2-(2-tert-butylanilino)-2-oxoacetate
• CAS: 959508-79-3
• 化学式: C₁₄H₁₉NO₃
• mdl: MFCD10018352
• 分子量: 249.31
• InChiKey: DPFZZLSEANVIOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-tert-butylanilino)-2-oxo-acetate 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 14.17h， 生成 3-(2-tert-butyl-phenyl)-1-((1S)-1-hydroxymethyl-2-methyl-propyl)-4,5-dihydro-3H-imidazol-1-ium hexafluorophosphate
  参考文献：
  名称：

  Design and synthesis of new bidentate alkoxy-NHC ligands for enantioselective copper-catalyzed conjugate addition

  摘要：

  A new family of chiral alkoxy-N-heterocyclic carbene (NHC) ligands has been designed for the enantioselective copper-catalyzed conjugate addition of dialkylzincs to enones. These new bidentate NHC ligands were synthesized in high overall yields using a five-step procedure starting from commercially available beta-aminoalcohols. Influence of the temperature, base, solvent and copper source were studied in order to optimize the stereoselectivity of the addition. High reactivity and excellent enantioselectivity were obtained at ambient temperature with a range of cyclic enones and dialkylzinc. Addition to acyclic enones has also been studied. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.04.027
• 作为产物：
  描述：

  2-叔丁基苯胺 、 草酰氯单乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.25h， 生成 ethyl 2-(2-tert-butylanilino)-2-oxo-acetate
  参考文献：
  名称：

  一系列含有γ-氨基酸部分的胱天蛋白酶抑制剂治疗胆汁淤积性肝病的构效关系研究

  摘要：

  已经合成了一系列含有γ-氨基酸部分的胱天蛋白酶抑制剂。对其抗凋亡细胞活性的构效关系进行了系统的研究。这些努力导致了化合物20o作为有效的半胱天冬酶抑制剂的发现，证明了临床前改善总胆红素功效并显着改善了药代动力学。

  DOI：

  10.1016/j.bmcl.2018.04.002

文献信息

• Structure-activity relationship study of a series of caspase inhibitors containing γ-amino acid moiety for treatment of cholestatic liver disease
  作者：Jianfeng Mou、Songliang Wu、Zhi Luo、Fengying Guo、Haiying He、Jianhua Wang、Fusen Lin、Fengxun Guo、Jianping Sun、Liang Shen、Minggao Zeng、Chuan Wang、Deming Xu、Zhengxian Gu、Xin Tian、Aiming Zhang、Hongjiang Xu、Ling Yang、Xiquan Zhang、Jian Li、Shuhui Chen

  DOI：10.1016/j.bmcl.2018.04.002

  日期：2018.6

  A series of caspase inhibitors containing γ-amino acid moiety have been synthesized. A systemic study on their structure-activity relationship of anti-apoptotic cellular activity is presented. These efforts led to the discovery of compound 20o as a potent caspase inhibitor, which demonstrated preclinical ameliorating total bilirubin efficacy with a significantly improved pharmacokinetic profile.

  已经合成了一系列含有γ-氨基酸部分的胱天蛋白酶抑制剂。对其抗凋亡细胞活性的构效关系进行了系统的研究。这些努力导致了化合物20o作为有效的半胱天冬酶抑制剂的发现，证明了临床前改善总胆红素功效并显着改善了药代动力学。
• Design and synthesis of new bidentate alkoxy-NHC ligands for enantioselective copper-catalyzed conjugate addition
  作者：Hervé Clavier、Ludovic Coutable、Loïc Toupet、Jean-Claude Guillemin、Marc Mauduit

  DOI：10.1016/j.jorganchem.2005.04.027

  日期：2005.11

  A new family of chiral alkoxy-N-heterocyclic carbene (NHC) ligands has been designed for the enantioselective copper-catalyzed conjugate addition of dialkylzincs to enones. These new bidentate NHC ligands were synthesized in high overall yields using a five-step procedure starting from commercially available beta-aminoalcohols. Influence of the temperature, base, solvent and copper source were studied in order to optimize the stereoselectivity of the addition. High reactivity and excellent enantioselectivity were obtained at ambient temperature with a range of cyclic enones and dialkylzinc. Addition to acyclic enones has also been studied. (c) 2005 Elsevier B.V. All rights reserved.