succinimido-2-[[2-phenyl-1-thioxo]thio]propanoate | 881212-56-2

• 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: succinimido-2-[[2-phenyl-1-thioxo]thio]propanoate
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 2-(benzenecarbonothioylsulfanyl)propanoate；(2,5-dioxopyrrolidin-1-yl) 2-(benzenecarbonothioylsulfanyl)propanoate
• CAS: 881212-56-2
• 化学式: C₁₄H₁₃NO₄S₂
• 分子量: 323.394
• InChiKey: SJYZTKQLFRBQJV-UHFFFAOYSA-N

物化性质

• 沸点：
  453.6±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  succinimido-2-[[2-phenyl-1-thioxo]thio]propanoate 、 N-生物素-3,6-二氧杂辛烷-1,8-二胺 以 氯仿 为溶剂， 反应 2.0h， 以72%的产率得到N-[8-((+)-biotinamido)-3,6-dioxaoctyl]-2-[[2-phenyl-1-thioxo]thio]propanamide
  参考文献：
  名称：

  Versatile Precursors of Functional RAFT Agents. Application to the Synthesis of Bio-Related End-Functionalized Polymers

  摘要：

  Biomolecule-polymer conjugates are widely used in bio-related fields, but their synthesis is often tricky, especially the introduction of a single biomolecule at one chain end. This paper describes a new straightforward approach to prepare such conjugates via RAFT polymerization. By designing appropriate bio-related RAFT agents, polymer chains of controlled chain length (Mn = 10 000-40 000 and PDI < 1.1) carrying a single biomolecule as an alpha-end group (a sugar or a biotin) linked by a stable amide bond are obtained. Considering the versatility of the RAFT process, this strategy appears to be very attractive for the design of a variety of conjugates.

  DOI：

  10.1021/ja057481c
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 2-(硫代苯甲酰硫基)丙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 23.0h， 生成 succinimido-2-[[2-phenyl-1-thioxo]thio]propanoate
  参考文献：
  名称：

  Versatile Precursors of Functional RAFT Agents. Application to the Synthesis of Bio-Related End-Functionalized Polymers

  摘要：

  Biomolecule-polymer conjugates are widely used in bio-related fields, but their synthesis is often tricky, especially the introduction of a single biomolecule at one chain end. This paper describes a new straightforward approach to prepare such conjugates via RAFT polymerization. By designing appropriate bio-related RAFT agents, polymer chains of controlled chain length (Mn = 10 000-40 000 and PDI < 1.1) carrying a single biomolecule as an alpha-end group (a sugar or a biotin) linked by a stable amide bond are obtained. Considering the versatility of the RAFT process, this strategy appears to be very attractive for the design of a variety of conjugates.

  DOI：

  10.1021/ja057481c

文献信息

• Novel Malachite Green- and Rhodamine B-labeled cationic chain transfer agents for RAFT polymerization
  作者：Mariana Beija、Carlos A.M. Afonso、José Paulo S. Farinha、Marie-Thérèse Charreyre、José M.G. Martinho

  DOI：10.1016/j.polymer.2011.10.041

  日期：2011.12

  MG-labeled dithiobenzoate (MGEDBA) was prepared in a straightforward manner after synthesis of MG-ethylammonium chloride that reacted with a precursor dithiobenzoate bearing an activated ester function. However, the analogous reaction with RhoB amino derivative led to a mixture of dithiobenzoate and thioamide derivatives. An alternative approach yielded the RhoB-labeled RAFT agent (RhoBEDBA) with complete

  已经合成了两种新颖的阳离子RAFT试剂，一种用孔雀石绿（MG）染料标记，另一种用若丹明B（RhoB）染料标记。MG标记的二硫代苯甲酸酯（MG​​EDBA）是在合成MG-乙基氯化铵后与包含活化酯功能的前体二硫代苯甲酸酯反应而直接制备的。然而，与RhoB氨基衍生物的类似反应导致二硫代苯甲酸酯和硫代酰胺衍生物的混合物。一种替代方法产生具有完全转化的RhoB标记的RAFT试剂（RhoBEDBA）。这些染料标记的RAFT试剂由于其双重性质（芳香族和离子性）而纯化非常具有挑战性。MGEDBA和RhoBEDBA都是控制N，N聚合的有效RAFT链转移剂-二甲基丙烯酰胺（DMA）。所得的α-末端标记的MG-和RhoB-PDMA样品具有较低的分散度（Đ <1.2），并且两个链端均得到保留。最后，我们表明RhoB和MG在PDMA聚合物链端的附着不会影响这些染料的光物理性质。因此，这些新型的染料标记的RAFT试剂
• RAFT polymerization and self-assembly of thermoresponsive poly(N-decylacrylamide-b-N,N-diethylacrylamide) block copolymers bearing a phenanthrene fluorescent α-end group
  作者：Telmo J.V. Prazeres、Mariana Beija、Marie-Thérèse Charreyre、José Paulo S. Farinha、José M.G. Martinho

  DOI：10.1016/j.polymer.2009.11.055

  日期：2010.1

  Phenanthrene alpha-end-labeled poly(N-decylacrylamide-b-N,N-diethylacrylamide) (PDcA(n)-b-PDEA(m)) block copolymers consisting in a highly hydrophobic block (n = 11) and a thermo responsive block with variable length (79 <= m <= 468) were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization. A new phenanthrene-labeled chain transfer agent (CTA) was synthesized and used to control the RAFT polymerization of a hydrophobic acrylamide derivative, N-decylacrylamide (DcA). This first block was further used as macroCTA to polymerize N,N-diethylacrylamide (DEA) in order to prepare diblock copolymers with the same hydrophobic block of PDcA (number average molecular weight: M-n = 2720 g mol(-1), polydispersity index: M-w/M-n = 1.13) and various PDEA blocks of several lengths M-n = 10,000-60,000 g mol(-1)) with a very high blocking efficiency. The resulting copolymers self-assemble in water forming thermoresponsive micelles. The critical micelle concentration (CMC) was determined using Forster resonance energy transfer (FRET) between phenanthrene linked at the end of the PDcA block and anthracene added to the solution at a low concentration (10(-5) M), based on the fact that energy transfer only occurs when phenanthrene and anthracene are located in the core of the micelle. The CMC (similar to 2 mu M) was obtained at the polymer concentration where the anthracene fluorescence intensity starts to increase. The size of the polymer micelles decreases with temperature increase around the lower critical solution temperature of PDEA in water (LCST similar to 32 degrees C) owing to the thermoresponsiveness of the PDEA shell. (C) 2009 Elsevier Ltd. All rights reserved.
• POLYMERIC FLUOROPHORES, COMPOSITIONS COMPRISING THE SAME, AND METHODS OF PREPARING AND USING THE SAME
  申请人：North Carolina State University

  公开号：US20200385583A1

  公开（公告）日：2020-12-10

  Described herein are polymeric fluorophores that include a dye, a polymer, and optionally a bioconjugate group. A polymeric fluorophore may have a structure represented by: A-B-C or C-A-B, wherein A is a dye; B is a polymer comprising one or more hydrophobic unit(s) and one or more hydrophilic unit(s); and optionally C, wherein C, when present, comprises a bioconjugate group. Also described herein are compositions comprising the polymeric fluorophores and methods of preparing and using the same.
• POLYMERIC CHROMOPHORES, COMPOSITIONS COMPRISING THE SAME, AND METHODS OF PREPARING AND USING THE SAME
  申请人：North Carolina State University

  公开号：US20220034873A1

  公开（公告）日：2022-02-03

  Described herein are polymeric chromophores that include a dye, a polymer, and optionally a bioconjugate group. A polymeric chromophore may have a structure represented by: A-B-C or C-A-B, wherein A is a dye; B is a polymer comprising one or more hydrophobic unit(s) and one or more hydrophilic unit(s); and optionally C, wherein C, when present, comprises a bioconjugate group. Also described herein are compositions comprising the polymeric chromophores and methods of preparing and using the same.
• [EN] NOVEL FUNCTIONALISED TRANSFER AGENTS FOR CONTROLLED RADICAL POLYMERISATION RAFT, RAFT METHODS USING SAID TRANSFER AGENTS AND POLYMERS OBTAINABLE THEREBY<br/>[FR] NOUVEAUX AGENTS DE TRANSFERT FONCTIONNALISES POUR POLYMERISATION RADICALAIRE CONTROLEE RAFT, PROCEDES RAFT METTANT EN OEVRE DE TELS AGENTS DE TRANSFERT ET POLYMERES SUSCEPTIBLES D'ETRE OBTENUS PAR DE TELS PROCEDES
  申请人：BIOMERIEUX SA

  公开号：WO2007003782A2

  公开（公告）日：2007-01-11

  [EN] The invention relates to chain reversible transfer agents used for a RAFT polymerisation and belonging to a dithioester, xanthate or a trithiocarbonate family comprising a group of formula (I), wherein R is a group containing at least one active ester function or a group of formula (II), wherein R' is a group containing at least one L-amide function, and L is selected between biological ligands, mono- or disaccharides, lipids, colorants, fluorescent molecules, polymer chains and solid carriers (II).
  [FR] L'invention a pour objet des agents de transfert réversible de chaîne pour polymérisation RAFT, appartenant à la famille des dithioesters, à la famille des xanthates ou à la famille des trithiocarbonates, comprenant un groupement de formule (I), dans lequel R est un groupe qui comprend au moins une fonction ester activé (I), ou bien comprenant un groupement de formule (II), dans lequel R' est un groupe qui comprend au moins une fonction amide-L, avec L choisi parmi les ligands biologiques, les mono- ou disaccharides, les lipides, les colorants, les molécules fluorescentes, les chaînes polymères et les supports solides (II).