2-甲基-2-丙基[1-(2-甲氧基苯基)乙基]氨基甲酸酯 | 701939-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-甲基-2-丙基[1-(2-甲氧基苯基)乙基]氨基甲酸酯
• 英文名称: (S)-[1-(2-methoxyphenyl)ethyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl (S)-1-(2-methoxyphenyl)ethylcarbamate；Tert-butyl [(1S)-1-(2-methoxyphenyl)ethyl]carbamate；tert-butyl N-[(1S)-1-(2-methoxyphenyl)ethyl]carbamate
• CAS: 701939-01-7
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: GXUWQUDCOIALDO-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基[1-(2-甲氧基苯基)乙基]氨基甲酸酯 在 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 三氟乙酸 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 22.0h， 生成 (S)-1-(2-methoxy-5-morpholin-4-ylphenyl)ethylamine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of Acrylamides as KCNQ2 Potassium Channel Openers

  摘要：

  A new class of acrylamides was synthesized, and the effects of these analogues on outward potassium current were evaluated by using two electrode voltage clamp recordings from Xenopus laevis oocytes expressing cloned mKCNQ2 channels. SAR studies indicated that the pharmacophore of the acrylamide series includes the (S) absolute configuration at the (1-phenyl)ethyl moiety and the alpha,beta-unsaturated acrylamide functionality with a free NH. This study identified (S)-N-[1-(3-morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide ((S)-1) and (S)-N-[1-(4-fluoro-3morpholin-4-yl-phenyl)-ethyl]-3-(4-fluoro-phenyl)-acrylamide ((S)-2) as KCNQ2 openers for further electrophysiological evaluations. These two acrylamides demonstrated significant activity in the cortical spreading depression model of migraine as we reported previously.

  DOI：

  10.1021/jm0305826
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (S)-1-(2-甲氧苯基)乙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-甲基-2-丙基[1-(2-甲氧基苯基)乙基]氨基甲酸酯
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of Acrylamides as KCNQ2 Potassium Channel Openers

  摘要：

  A new class of acrylamides was synthesized, and the effects of these analogues on outward potassium current were evaluated by using two electrode voltage clamp recordings from Xenopus laevis oocytes expressing cloned mKCNQ2 channels. SAR studies indicated that the pharmacophore of the acrylamide series includes the (S) absolute configuration at the (1-phenyl)ethyl moiety and the alpha,beta-unsaturated acrylamide functionality with a free NH. This study identified (S)-N-[1-(3-morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide ((S)-1) and (S)-N-[1-(4-fluoro-3morpholin-4-yl-phenyl)-ethyl]-3-(4-fluoro-phenyl)-acrylamide ((S)-2) as KCNQ2 openers for further electrophysiological evaluations. These two acrylamides demonstrated significant activity in the cortical spreading depression model of migraine as we reported previously.

  DOI：

  10.1021/jm0305826

文献信息

• N-Octanoyldimethylglycine Trifluoroethyl Ester, an Acyl Donor Leading to Highly Enantioselective Protease-Catalysed Kinetic Resolution of Amines
  作者：Severine Queyroy、Nicolas Vanthuyne、Stéphane Gastaldi、Michèle P. Bertrand、Gérard Gil

  DOI：10.1002/adsc.201100993

  日期：2012.6.18

  The use of N‐octanoyldimethylglycine trifluoroethyl ester as acyl donor in the kinetic resolution of aliphatic amines catalysed by proteases led to enantiomeric ratios >200 in most cases. The resolutions mediated by Protex 6L were shown to be much faster than the resolutions achieved with the most efficient commercially available serine proteases, i.e., alkaline protease, Properase 1600L, and Subtilisin

  在大多数情况下，在蛋白酶催化的脂肪族胺的动力学拆分中，使用N-辛酰基二甲基甘氨酸三氟乙基酯作为酰基供体会导致对映体比率> 200。已证明，由Protex 6L介导的分辨率比使用最有效的市售丝氨酸蛋白酶（即碱性蛋白酶，Properase 1600L和枯草杆菌蛋白酶）获得的分辨率快得多。