tert-butyl ((2S,3R,S)-4,4,4-trifluoro-3-hydroxy-2-butanyl)carbamate | 1009606-40-9

• 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: tert-butyl ((2S,3R,S)-4,4,4-trifluoro-3-hydroxy-2-butanyl)carbamate
• 英文别名: tert-butyl (2S,3R)-4,4,4-trifluoro-3-hydroxybutan-2-ylcarbamate
• CAS: 1009606-40-9
• 化学式: C₉H₁₆F₃NO₃
• 分子量: 243.226
• InChiKey: HIVJJBUFQGEXBV-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((2S,3R,S)-4,4,4-trifluoro-3-hydroxy-2-butanyl)carbamate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以81%的产率得到(4S,5R)-4-methyl-5-(trifluoromethyl)oxazolidin-2-one
  参考文献：
  名称：

  An Efficient Entry to Optically Active anti- and syn-β-Amino-α-trifluoromethyl Alcohols

  摘要：

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.

  DOI：

  10.1021/ol702947n
• 作为产物：
  描述：

  (2R,3S)-3-(benzyl((R)-2-hydroxy-1-phenylethyl)amino)-1,1,1-trifluorobutan-2-ol 、 二碳酸二叔丁酯 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以58%的产率得到tert-butyl ((2S,3R,S)-4,4,4-trifluoro-3-hydroxy-2-butanyl)carbamate
  参考文献：
  名称：

  An Efficient Entry to Optically Active anti- and syn-β-Amino-α-trifluoromethyl Alcohols

  摘要：

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.

  DOI：

  10.1021/ol702947n

文献信息

• Plasmodium falciparum subtilisin-like protease 1: discovery of potent difluorostatone-based inhibitors
  作者：Simone Giovani、Maria Penzo、Stefania Butini、Margherita Brindisi、Sandra Gemma、Ettore Novellino、Giuseppe Campiani、Michael J. Blackman、Simone Brogi

  DOI：10.1039/c5ra01170a

  日期：——

  available drugs to treat malaria are often ineffective due to the acquisition of drug resistance. In this context, drugs with innovative modes of action and no liability to cross-resistance are urgently needed. Recently, subtilisin-like protease 1, a P. falciparum serine protease involved in merozoite egress from red blood cells and invasion, has been identified as potential drug target. We describe

  由于获得抗药性，目前可用于治疗疟疾的药物通常无效。在这种情况下，迫切需要具有创新作用方式且对交叉耐药性不承担责任的药物。最近，枯草杆菌蛋白酶样蛋白酶1，一种恶性疟原虫丝氨酸蛋白酶，参与了裂殖子从红细胞中逸出并侵入，已被确定为潜在的药物靶标。我们在本文中描述了一系列有效的PfSUB1抑制剂的开发。结合简单的合成方法，深入的结构活性研究和计算机模拟研究，我们确定了迄今为止已知的最有效的抑制剂，其特征在于与原型肽相比，具有更高的酶抑制能力和降低的肽特性。