benzyl 2-(2-methyl-1,3-dioxolan-2-yl)ethyltrithiocarbonate | 1395347-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-(2-methyl-1,3-dioxolan-2-yl)ethyltrithiocarbonate
• 英文别名: Benzylsulfanyl-[2-(2-methyl-1,3-dioxolan-2-yl)ethylsulfanyl]methanethione；benzylsulfanyl-[2-(2-methyl-1,3-dioxolan-2-yl)ethylsulfanyl]methanethione
• CAS: 1395347-04-2
• 化学式: C₁₄H₁₈O₂S₃
• 分子量: 314.494
• InChiKey: IRDHAOVWWRPBMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2-(2-methyl-1,3-dioxolan-2-yl)ethyltrithiocarbonate 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-Benzylsulfanylcarbothioylsulfanylbutan-2-one
  参考文献：
  名称：

  Z-Group Ketone Chain Transfer Agents for RAFT Polymer Nanoparticle Modification via Hydrazone Conjugation

  摘要：

  A ketal-containing trithiocarbonyl compound has been synthesized and characterized as a chain transfer agent (CTA) in reversible addition fragmentation transfer (RAFT) polymerization. The ketal functionality does not interfere with RAFT polymerization of acrylate monomers, which proceeds as previously reported to yield macro-CTA polymers and block copolymers. Postpolymerization ketal cleavage revealed ketone functionality at the polar terminus of an amphiphilic block copolymer. Hydrazone formation was facile in both organic solution and aqueous buffer where polymer nanoparticle assemblies were formed, indicating a conjugation/end-functionalization yield of 40-50%. Conjugation was verified with fluorescein, biotin, and Gd-DOTA derivatives, and though the trithiocarbonate linkage is hydrolytically labile, we observed stable conjugation for several days at pH 7.4. and 37 degrees C. As expected, streptavidin binding to biotinylated polymer micelles was observed, and size-change-based relaxivity increases were observed when Gd-DOTA hydrazide was conjugated to polymer micelles. Cell uptake of fluorescently labeled polymer micelles was also readily tracked by FACS and fluorescence microscopy. These polymer derivatives demonstrate a range of potential theranostic/biotechnological applications for this conveniently accessible keto-CTA, which include ligand-based nanoparticle targeting and fluorescent/MR nanoparticle contrast agents.

  DOI：

  10.1021/ma301536f
• 作为产物：
  描述：

  S-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl] ethanethioate 、 溴甲苯 在 甲醇 、 水 、 sodium hydroxide 、 二硫化碳 、 碳酸氢钠 作用下， 反应 0.5h， 以78%的产率得到benzyl 2-(2-methyl-1,3-dioxolan-2-yl)ethyltrithiocarbonate
  参考文献：
  名称：

  Z-Group Ketone Chain Transfer Agents for RAFT Polymer Nanoparticle Modification via Hydrazone Conjugation

  摘要：

  A ketal-containing trithiocarbonyl compound has been synthesized and characterized as a chain transfer agent (CTA) in reversible addition fragmentation transfer (RAFT) polymerization. The ketal functionality does not interfere with RAFT polymerization of acrylate monomers, which proceeds as previously reported to yield macro-CTA polymers and block copolymers. Postpolymerization ketal cleavage revealed ketone functionality at the polar terminus of an amphiphilic block copolymer. Hydrazone formation was facile in both organic solution and aqueous buffer where polymer nanoparticle assemblies were formed, indicating a conjugation/end-functionalization yield of 40-50%. Conjugation was verified with fluorescein, biotin, and Gd-DOTA derivatives, and though the trithiocarbonate linkage is hydrolytically labile, we observed stable conjugation for several days at pH 7.4. and 37 degrees C. As expected, streptavidin binding to biotinylated polymer micelles was observed, and size-change-based relaxivity increases were observed when Gd-DOTA hydrazide was conjugated to polymer micelles. Cell uptake of fluorescently labeled polymer micelles was also readily tracked by FACS and fluorescence microscopy. These polymer derivatives demonstrate a range of potential theranostic/biotechnological applications for this conveniently accessible keto-CTA, which include ligand-based nanoparticle targeting and fluorescent/MR nanoparticle contrast agents.

  DOI：

  10.1021/ma301536f

文献信息

• Z-Group Ketone Chain Transfer Agents for RAFT Polymer Nanoparticle Modification via Hydrazone Conjugation
  作者：Saibal Bandyopadhyay、Xin Xia、Andrei Maiseiyeu、Georgeta Mihai、Sanjay Rajagopalan、Dennis Bong

  DOI：10.1021/ma301536f

  日期：2012.9.11

  A ketal-containing trithiocarbonyl compound has been synthesized and characterized as a chain transfer agent (CTA) in reversible addition fragmentation transfer (RAFT) polymerization. The ketal functionality does not interfere with RAFT polymerization of acrylate monomers, which proceeds as previously reported to yield macro-CTA polymers and block copolymers. Postpolymerization ketal cleavage revealed ketone functionality at the polar terminus of an amphiphilic block copolymer. Hydrazone formation was facile in both organic solution and aqueous buffer where polymer nanoparticle assemblies were formed, indicating a conjugation/end-functionalization yield of 40-50%. Conjugation was verified with fluorescein, biotin, and Gd-DOTA derivatives, and though the trithiocarbonate linkage is hydrolytically labile, we observed stable conjugation for several days at pH 7.4. and 37 degrees C. As expected, streptavidin binding to biotinylated polymer micelles was observed, and size-change-based relaxivity increases were observed when Gd-DOTA hydrazide was conjugated to polymer micelles. Cell uptake of fluorescently labeled polymer micelles was also readily tracked by FACS and fluorescence microscopy. These polymer derivatives demonstrate a range of potential theranostic/biotechnological applications for this conveniently accessible keto-CTA, which include ligand-based nanoparticle targeting and fluorescent/MR nanoparticle contrast agents.