ethyl 2-(3-bromopropylimino)-2-(4-fluorophenyl)acetate | 1080671-46-0

• 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-(3-bromopropylimino)-2-(4-fluorophenyl)acetate
• CAS: 1080671-46-0
• 化学式: C₁₃H₁₅BrFNO₂
• 分子量: 316.17
• InChiKey: BAQKLVAUQMFZCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-bromopropylimino)-2-(4-fluorophenyl)acetate 在 sodium tetrahydroborate 、 potassium tert-butylate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.5h， 生成 (S,E)-3-(4-fluorophenyl)-8-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)-3-(methoxymethyl)-5,6,7,8-tetrahydro-3H-[1,2,4]oxadiazolo[4,3-a]pyridine
  参考文献：
  名称：

  Cyclic Hydroxyamidines as Amide Isosteres: Discovery of Oxadiazolines and Oxadiazines as Potent and Highly Efficacious γ-Secretase Modulators in Vivo

  摘要：

  Cyclic hydroxyamidines were designed and validated as isosteric replacements of the amide functionality. Compounds with these structural motifs were found to be metabolically stable and to possess highly desirable pharmacokinetic profiles. These designs were applied in the identification of gamma-secretase modulators leading to highly efficacious agents for reduction of central nervous system A beta(42) in various animal models.

  DOI：

  10.1021/jm201407j
• 作为产物：
  描述：

  4-氟苯基乙醛酸乙酯 、 3-溴-N,N-双(三甲基甲硅烷基)丙烷-1-胺 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以332 g的产率得到ethyl 2-(3-bromopropylimino)-2-(4-fluorophenyl)acetate
  参考文献：
  名称：

  Cyclic Hydroxyamidines as Amide Isosteres: Discovery of Oxadiazolines and Oxadiazines as Potent and Highly Efficacious γ-Secretase Modulators in Vivo

  摘要：

  Cyclic hydroxyamidines were designed and validated as isosteric replacements of the amide functionality. Compounds with these structural motifs were found to be metabolically stable and to possess highly desirable pharmacokinetic profiles. These designs were applied in the identification of gamma-secretase modulators leading to highly efficacious agents for reduction of central nervous system A beta(42) in various animal models.

  DOI：

  10.1021/jm201407j

文献信息

• WO2008/137139
  申请人：——

  公开号：——

  公开（公告）日：——
• Cyclic Hydroxyamidines as Amide Isosteres: Discovery of Oxadiazolines and Oxadiazines as Potent and Highly Efficacious γ-Secretase Modulators in Vivo
  作者：Zhong-Yue Sun、Theodros Asberom、Thomas Bara、Chad Bennett、Duane Burnett、Inhou Chu、John Clader、Mary Cohen-Williams、David Cole、Michael Czarniecki、James Durkin、Gioconda Gallo、William Greenlee、Hubert Josien、Xianhai Huang、Lynn Hyde、Nicholas Jones、Irina Kazakevich、Hongmei Li、Xiaoxiang Liu、Julie Lee、Malcolm MacCoss、Mihir B. Mandal、Troy McCracken、Amin Nomeir、Robert Mazzola、Anandan Palani、Eric M. Parker、Dmitri A. Pissarnitski、Jun Qin、Lixin Song、Giuseppe Terracina、Monica Vicarel、Johannes Voigt、Ruo Xu、Lili Zhang、Qi Zhang、Zhiqiang Zhao、Xiaohong Zhu、Zhaoning Zhu

  DOI：10.1021/jm201407j

  日期：2012.1.12

  Cyclic hydroxyamidines were designed and validated as isosteric replacements of the amide functionality. Compounds with these structural motifs were found to be metabolically stable and to possess highly desirable pharmacokinetic profiles. These designs were applied in the identification of gamma-secretase modulators leading to highly efficacious agents for reduction of central nervous system A beta(42) in various animal models.