2-((2-hydroxyethyl)disulfanyl)ethyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate | 1421969-29-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-((2-hydroxyethyl)disulfanyl)ethyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate
• 英文别名: 2-(2-Hydroxyethyldisulfanyl)ethyl 4-(benzenecarbonothioylsulfanyl)-4-cyanopentanoate；2-(2-hydroxyethyldisulfanyl)ethyl 4-(benzenecarbonothioylsulfanyl)-4-cyanopentanoate
• CAS: 1421969-29-0
• 化学式: C₁₇H₂₁NO₃S₄
• 分子量: 415.623
• InChiKey: RWDYNHUISWZOSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-((2-hydroxyethyl)disulfanyl)ethyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate 、 丙烯酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以80.2%的产率得到2-((2-(acryloyloxy)ethyl)disulfanyl)ethyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate
  参考文献：
  名称：

  Synthesis and Properties of Multicleavable Amphiphilic Dendritic Comblike and Toothbrushlike Copolymers Comprising Alternating PEG and PCL Grafts

  摘要：

  Facile construction of novel functional den dritic copolymers by combination of self-condensing vinyl polymerization, sequence-controlled copolymerization and RAFT process was presented. RAFT copolymerization of a disulfide-linked polymerizable RAFT agent and equimolar feed ratio of styrenic and maleimidic macromonomers afforded multicleavable A(m)B(n) dendritic comblike copolymers with alternating PEG (A) and PCL (B) grafts, and a subsequent chain extension polymerization of styrene, tert-butyl acrylate, methyl methacrylate, and N-isopropylacrylamide gave A(m)B(n)C(o) dendritic toothbrushlike copolymers. (PEG)(m)(PCL)(n) copolymers obtained were of adjustable molecular weight, relatively low polydispersity (PDI = 1.10-1.32), variable CTA functionality (f(CTA) = 4.3-7.5), and similar segment numbers of PEG and PCL grafts, evident from H-1 NMR and GPC-MALLS analyses. Their branched architecture was confirmed by (a) reduction-triggered degradation, (b) decreased intrinsic viscosities and Mark-Houwink-Sakurada exponent than their "linear" analogue, and (c) lowered glass transition and melting temperatures and broadened melting range as compared with normal A(m)B(n) comblike copolymer. In vitro drug release results revealed that the drug release kinetics of the disulfide-linked A(m)B(n) copolymer aggregates was significantly affected by macromolecular architecture, end group and reductive stimulus. These stimuli-responsive and biodegradable dendritic copolymer aggregates had a great potential as controlled delivery vehicles.

  DOI：

  10.1021/ma3025283

文献信息

• Synthesis and Properties of Multicleavable Amphiphilic Dendritic Comblike and Toothbrushlike Copolymers Comprising Alternating PEG and PCL Grafts
  作者：Meijing Zhang、Huanhuan Liu、Wei Shao、Ke Miao、Youliang Zhao

  DOI：10.1021/ma3025283

  日期：2013.2.26

  Facile construction of novel functional den dritic copolymers by combination of self-condensing vinyl polymerization, sequence-controlled copolymerization and RAFT process was presented. RAFT copolymerization of a disulfide-linked polymerizable RAFT agent and equimolar feed ratio of styrenic and maleimidic macromonomers afforded multicleavable A(m)B(n) dendritic comblike copolymers with alternating PEG (A) and PCL (B) grafts, and a subsequent chain extension polymerization of styrene, tert-butyl acrylate, methyl methacrylate, and N-isopropylacrylamide gave A(m)B(n)C(o) dendritic toothbrushlike copolymers. (PEG)(m)(PCL)(n) copolymers obtained were of adjustable molecular weight, relatively low polydispersity (PDI = 1.10-1.32), variable CTA functionality (f(CTA) = 4.3-7.5), and similar segment numbers of PEG and PCL grafts, evident from H-1 NMR and GPC-MALLS analyses. Their branched architecture was confirmed by (a) reduction-triggered degradation, (b) decreased intrinsic viscosities and Mark-Houwink-Sakurada exponent than their "linear" analogue, and (c) lowered glass transition and melting temperatures and broadened melting range as compared with normal A(m)B(n) comblike copolymer. In vitro drug release results revealed that the drug release kinetics of the disulfide-linked A(m)B(n) copolymer aggregates was significantly affected by macromolecular architecture, end group and reductive stimulus. These stimuli-responsive and biodegradable dendritic copolymer aggregates had a great potential as controlled delivery vehicles.