2-tert-butyldimethylsilyloxy-3-(1H-indol-3-yl)-N-methoxy-N-methylpropanamide | 157163-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-tert-butyldimethylsilyloxy-3-(1H-indol-3-yl)-N-methoxy-N-methylpropanamide
• 英文别名: N-Methoxy-N-methyl-2-t-butyldimethylsilyloxy-3-(3-indolyl)propionamide；2-[tert-butyl(dimethyl)silyl]oxy-3-(1H-indol-3-yl)-N-methoxy-N-methylpropanamide
• CAS: 157163-62-7
• 化学式: C₁₉H₃₀N₂O₃Si
• 分子量: 362.544
• InChiKey: ICXORUNVPRXPLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 2-hydroxy-3-(1H-indol-3-yl)-N-methoxy-N-methylpropanamide 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以81%的产率得到2-tert-butyldimethylsilyloxy-3-(1H-indol-3-yl)-N-methoxy-N-methylpropanamide
  参考文献：
  名称：

  A concise, total synthesis and antibacterial evaluation of 2-hydroxy-1-(1H-indol-3-yl)-4-methylpentan-3-one

  摘要：

  Treatment of racemic 2-hydroxy-3-(1H-indol-3yl)propionic acid methyl ester (5) with isopropyl magnesium chloride provided the title compound 1 and its isomer, 3-hydroxy-1-(indol-3-yl)-4-methylpentan-2-one (9). Both enantiomers (>96% ee) of each component were obtained via semi-preparative chiral supercritical fluid chromatography (SFC). In contrast to previous reports, these compounds, as well as their acetate derivatives, were not active or very weakly active against 16 bacterial strains, including Escherichia coli, Bacillus subtilis and Staphylococcus aureus. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.003

文献信息

• Imidazolinone derivatives as tachykinin receptor antagonists
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US05612362A1

  公开（公告）日：1997-03-18

  Compounds of formula (I) and salts and prodrugs wherein Q.sup.1 is a specified aryl group, the dotted line is an optional double bond, Z is O or NR.sup.3, R.sup.1 and R.sup.3 are H or specified optionally substituted alkyl or other substituents and R.sup.2 is an optionally substituted phenyl or group are tachykinin receptor antagonists useful in medicine.

  化合物的公式(I)及其盐和前药，其中Q.sup.1是特定的芳基基团，点线是可选的双键，Z是O或NR.sup.3，R.sup.1和R.sup.3是H或特定的可选择取代烷基或其他取代基，而R.sup.2是可选择取代的苯基或基团，是在医学上有用的Tachykinin受体拮抗剂。