2-(diphenylphosphaneyl)phenyl 4-cyano-4-(((dodecylthio)carbonothioyl)thio)pentanoate | 1292766-78-9

• 英文名称: 2-(diphenylphosphaneyl)phenyl 4-cyano-4-(((dodecylthio)carbonothioyl)thio)pentanoate
• CAS: 1292766-78-9
• 化学式: C₃₇H₄₆NO₂PS₃
• 分子量: 663.949
• InChiKey: BUFTUNTXFRUIBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.08
• 重原子数：
  44.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-氰基-4-[[(十二烷硫基)硫酮甲基]硫基]戊酸 、 (2-羟基苯基)二苯基膦 在 4-二甲氨基吡啶 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 2-(diphenylphosphaneyl)phenyl 4-cyano-4-(((dodecylthio)carbonothioyl)thio)pentanoate
  参考文献：
  名称：

  Combining RAFT and Staudinger Ligation: A Potentially New Synthetic Tool for Bioconjugate Formation

  摘要：

  We report a new route for biocompatible polymer end-group modification by means of the Staudinger ligation. This reaction allows the formation of a peptide bond in aqueous media between a phosphine-containing ester functionality and an azide group. Esterification of the two carboxylic acid-containing chain transfer agents (CTAs), 2-(dodecylsulfanylthiocarbonylsulfanyl)-2-methylpropionic acid (1) and 4-cyano-4-(dodecylsulfanylthiocarbonylsulfanyl)pentanoic acid (2), with different appropriate phosphines gave phosphine-containing CTAs. They allowed us to synthesize polystyrene of medium molecular weight via "reversible addition-fragmentation chain transfer" (RAFT) polymerization. 3,6,9-Trioxodecyl azide (TOD-N-3) was then used as model compound to study the Staudinger ligation with the corresponding polymers. Among all CTAs tested, the phosphine-functionalized CTA-4, prepared from 2 and P-borane-(diphenylphosphanyl)methanethiol (6), not only proved to be suitable for RAFT polymerization of styrene but the polymer-bound P-borane-(diphenylphosphanyl)methyl thioester group also showed the best performance in the subsequent polymer analogous Staudinger ligation.

  DOI：

  10.1021/ma2000724