5-oxo-5-(phenylthio)pentanoic acid | 1247948-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: 5-oxo-5-(phenylthio)pentanoic acid
• 英文别名: 5-Oxo-5-phenylsulfanylpentanoic acid；5-oxo-5-phenylsulfanylpentanoic acid
• CAS: 1247948-34-0
• 化学式: C₁₁H₁₂O₃S
• 分子量: 224.28
• InChiKey: NPRYBOYGKBZZSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-oxo-5-(phenylthio)pentanoic acid 、 microgonotropen 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 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 3.0h， 以49%的产率得到N-[3-(dimethylamine)propyl]-1-methyl-4-[(1-{3-(5-oxo-5-[phenylthio]pentanamido)propyl}-4-{[1-methyl-4-(methylcarboxamido)-1H-2-pyrrolyl]carboxamido}-1H-2-pyrrolyl)carboxamido]-1H-2-pyrrolecarboxamide
  参考文献：
  名称：

  Toward encoding reactivity using double-stranded DNA. Sequence-dependent native chemical ligation of DNA binding polyamides

  摘要：

  The coupling reaction between distamycin-related polyamides equipped with cysteine and thioester groups can be accelerated in the presence of double-stranded (ds) oligonucleotides with selected sequences. While the coupling reaction of reactive partners containing three pyrrole units is accelerated by dsDNAs containing ATTTTA or ATGTTA sites, the heterodimeric coupling between a tripyrrole and a polyamide equipped with two pyrroles and one imidazole, is accelerated by the latter DNA, but not by the other containing the A/T rich tract. These differences can be exploited for selecting preferred coupling pairs from a mixture of reactive monomers; therefore the reaction outcome depends on the instructions provided by the dsDNA sequence. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.126
• 作为产物：
  描述：

  戊二酸酐 、 二苯二硫醚 在 水 、 rongalite 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 以80%的产率得到5-oxo-5-(phenylthio)pentanoic acid
  参考文献：
  名称：

  A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite®

  摘要：

  Rongalite (R) promotes cleavage of diaryl disulfides generating chalcogenolate anions that then undergo facile acylation with anhydrides in the presence of CsF to afford thioesters (3) with good to excellent yields. By using the present protocol, 5-arylthio-5-oxopentanoic acid (4) can be facilely prepared. The important features of the methodology are broad substrate scope, simple operation, and no requirement for metal catalysts. It is noteworthy that acylations of diphenyl diselane with anhydrides are also conducted smoothly to afford selenoesters (5) in good yields under the standard conditions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.023