tert-butyl (S,E)-(4-fluoro-1-phenyl-4-(phenylsulfonyl)but-3-en-2-yl)carbamate | 1000699-48-8

• 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: tert-butyl (S,E)-(4-fluoro-1-phenyl-4-(phenylsulfonyl)but-3-en-2-yl)carbamate
• CAS: 1000699-48-8
• 化学式: C₂₁H₂₄FNO₄S
• 分子量: 405.49
• InChiKey: RTFISTIFURMPMP-BYFYWULKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S,E)-(4-fluoro-1-phenyl-4-(phenylsulfonyl)but-3-en-2-yl)carbamate 、 2-苯乙硫醇 在 三乙胺 作用下， 生成
  参考文献：
  名称：

  Dipeptidyl α-fluorovinyl Michael acceptors: Synthesis and activity against cysteine proteases

  摘要：

  The synthesis of novel dipeptidyl alpha-fluorovinyl sulfones using a Horner-Wadsworth-Emmons approach on N-Boc-L-phenylalaninal is described. Inhibitory assays against a Leishmania mexicana cysteine protease (CPB2.8 Delta CTE) revealed low biological activity. Relative rates of Michael additions of 2'-(phenethyl) thiol with vinyl sulfone and alpha-fluorovinyl sulfone were determined, and ab initio calculations on several Michael acceptor model structures were performed; both were in agreement with the biological testing results. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.075
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 、 氟代（苯磺酰）甲基膦酸二乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 tert-butyl (S,E)-(4-fluoro-1-phenyl-4-(phenylsulfonyl)but-3-en-2-yl)carbamate 、 tert-butyl (S,Z)-(4-fluoro-1-phenyl-4-(phenylsulfonyl)but-3-en-2-yl)carbamate
  参考文献：
  名称：

  Dipeptidyl α-fluorovinyl Michael acceptors: Synthesis and activity against cysteine proteases

  摘要：

  The synthesis of novel dipeptidyl alpha-fluorovinyl sulfones using a Horner-Wadsworth-Emmons approach on N-Boc-L-phenylalaninal is described. Inhibitory assays against a Leishmania mexicana cysteine protease (CPB2.8 Delta CTE) revealed low biological activity. Relative rates of Michael additions of 2'-(phenethyl) thiol with vinyl sulfone and alpha-fluorovinyl sulfone were determined, and ab initio calculations on several Michael acceptor model structures were performed; both were in agreement with the biological testing results. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.075