NBu-NCA | 1087763-33-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: NBu-NCA
• 英文别名: 3-Butyl-1,3-oxazolidine-2,5-dione；3-butyl-1,3-oxazolidine-2,5-dione
• CAS: 1087763-33-4
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: MSDHVIIHGYLEQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80 °C (decomp)
• 沸点：
  202.4±23.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯基硫三甲基硅烷 、 NBu-NCA 以 氘代氯仿 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  苯基三甲基甲硅烷基硫醚介导的α-氨基酸N-羧基氰化物的控制开环聚合

  摘要：

  我们在此描述三甲基甲硅烷基硫醚（S -TMS）介导的α-氨基酸N-羧基酐（NCA）的受控开环聚合（ROP）的第一个例子。我们表明，苯基三甲基甲硅烷基硫醚（PhS-TMS），一种便宜且可商购的化合物，介导NCA单体广泛范围的快速ROP，产生具有可控制的分子量（MWs），窄多分散性的功能性聚氨基酸（PAA）指数（PDI），以及在C处原位生成的苯基硫酯基-末端（PAA-SPhs）。与以前报道的六甲基二硅氮烷（HMDS）引发剂相比，PhS-TMS提供了更快的链引发作用，从而确保了可控制的活性聚合。机理研究表明，在链引发过程中会生成反应性氨基甲酸三甲基甲硅烷基酯（TMSC），并通过TMS转移过程继续调节链增长。考虑到NCA的多功能性以及利用C末端苯基硫代酯进行天然化学连接（NCL）的潜力，我们认为该方法可能提供一个强大的平台，能够快速生成功能性PAA及其C末端结合物，从而用于众多生物应用程序。

  DOI：

  10.1021/acs.biomac.5b01588
• 作为产物：
  描述：

  N-butylglycine hydrochloride 在 乙酸酐 、 乙酰氯 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 10.0h， 生成 NBu-NCA
  参考文献：
  名称：

  Polypeptoids from N-Substituted Glycine N-Carboxyanhydrides: Hydrophilic, Hydrophobic, and Amphiphilic Polymers with Poisson Distribution

  摘要：

  Preparation of defined and functional polymers has been one of the hottest topics in polymer science and drug delivery in the recent decade. Also, research on (bio)degradable polymers gains more and more interest, in particular at the interface of these two disciplines. However, in the majority of cases, combination of definition, functionality and degradability, is problematic. Here we present the preparation and characterization (MALDI-ToF MS, NMR, GPC) of nonionic hydrophilic, hydrophobic, and amphiphilic N-substituted polyglycines (polypeptoids), which are expected to be main-chain degradable and are able to disperse a hydrophobic model compound in aqueous media. Polymerization kinetics suggest that the polymerization is well controlled with strictly linear pseudo first-order kinetic plots to high monomer consumption. Moreover, molar mass distributions of products are Poisson-type and molar mass can be controlled by the monomer to initiator ratio. The presented polymer platform is nonionic, backbone degradable, and synthetically highly flexible and may therefore be valuable for a broad range of applications, in particular as a biomaterial.

  DOI：

  10.1021/ma201015y

文献信息

• Cyclic Poly(α-peptoid)s and Their Block Copolymers from N-Heterocyclic Carbene-Mediated Ring-Opening Polymerizations of N-Substituted <i>N</i>-Carboxylanhydrides
  作者：Li Guo、Donghui Zhang

  DOI：10.1021/ja907380d

  日期：2009.12.23

  sequential monomer addition. The cyclic polymer architectures were verified by MALDI-TOF mass spectrometry and intrinsic viscosity measurements. Mark-Houwink-Sakurada plot analyses revealed that cyclic poly(alpha-peptoid)s prepared from NHC-mediated polymerizations exhibit lower intrinsic viscosities than their linear analogues prepared from primary amine-initiated polymerizations. The ratio of their intrinsic

  N-取代的 N-羧基酐 ((N)R-NCA) 的 N-杂环卡宾 (NHC) 介导的开环聚合 (ROP) 产生具有受控分子量 (M(n) = 3-30 kg mol(-1)) 和窄分子量分布 (PDI = 1.04-1.12)。该反应表现出具有最小链转移的活性聚合特征。这使得可以通过顺序单体添加轻松合成环状二嵌段共聚（α-拟肽）。通过 MALDI-TOF 质谱和特性粘度测量验证了环状聚合物结构。Mark-Houwink-Sakurada 绘图分析显示，由 NHC 介导的聚合制备的环状聚 (α-拟肽) 比由伯胺引发的聚合制备的线性类似物具有更低的特性粘度。
• Precision Synthesis of Polysarcosine via Controlled Ring-Opening Polymerization of <i>N</i>-Carboxyanhydride: Fast Kinetics, Ultrahigh Molecular Weight, and Mechanistic Insights
  作者：Shuo Wang、Ming-Yuan Lu、Si-Kang Wan、Chun-Yan Lyu、Zi-You Tian、Kai Liu、Hua Lu

  DOI：10.1021/jacs.3c14740

  日期：2024.2.28

  rapid and controlled synthesis of high-molecular-weight (HMW) polysarcosine (pSar), a potential polyethylene glycol (PEG) alternative, via the ring-opening polymerization (ROP) of N-carboxyanhydride (NCA) is rare and challenging. Here, we report the well-controlled ROP of sarcosine NCA (Sar-NCA) that is catalyzed by various carboxylic acids, which accelerate the polymerization rate up to 50 times,

  通过N-羧酸酐 (NCA) 的开环聚合 (ROP) 快速、受控合成高分子量 (HMW) 聚肌氨酸 (pSar)（一种潜在的聚乙二醇 (PEG) 替代品）是罕见且具有挑战性的。在这里，我们报道了由各种羧酸催化的肌氨酸NCA（Sar-NCA）的良好控制的ROP，其将聚合速率提高了50倍，并且能够稳健地合成具有前所未有的超高分子量（UHMW）的pSar ) 高达 586 kDa (DP ∼ 8200)，且分散度 ( D̵ ) 极窄，低于 1.05。机理实验和密度泛函理论计算共同阐明了羧酸作为双功能催化剂的作用，可显着促进质子转移过程并避免电荷分离，并表明 NCA 的开环而不是脱羧作为速率决定步骤。 UHMW pSar 表现出比低分子量同类产品更高的热性能和机械性能。这项工作为 UHMW pSar 提供了一种简单而高效的方法，并产生了新的基本理解，不仅对 Sar-NCA 的 ROP 有用，而且对其他
• Phenyl Trimethylsilyl Sulfide-Mediated Controlled Ring-Opening Polymerization of α-Amino Acid <i>N</i>-Carboxyanhydrides
  作者：Jingsong Yuan、Yunlong Sun、Jingyu Wang、Hua Lu

  DOI：10.1021/acs.biomac.5b01588

  日期：2016.3.14

  generated phenyl thioester group at the C-terminus (PAA-SPhs). PhS-TMS offers more rapid chain initiation than previously reported hexamethyldisilazane (HMDS) initiator, ensuring a living polymerization with better control. Mechanistic studies suggest that a reactive trimethylsilyl carbamate (TMSC) was generated during the chain initiation and continued to regulate the chain propagation through a TMS

  我们在此描述三甲基甲硅烷基硫醚（S -TMS）介导的α-氨基酸N-羧基酐（NCA）的受控开环聚合（ROP）的第一个例子。我们表明，苯基三甲基甲硅烷基硫醚（PhS-TMS），一种便宜且可商购的化合物，介导NCA单体广泛范围的快速ROP，产生具有可控制的分子量（MWs），窄多分散性的功能性聚氨基酸（PAA）指数（PDI），以及在C处原位生成的苯基硫酯基-末端（PAA-SPhs）。与以前报道的六甲基二硅氮烷（HMDS）引发剂相比，PhS-TMS提供了更快的链引发作用，从而确保了可控制的活性聚合。机理研究表明，在链引发过程中会生成反应性氨基甲酸三甲基甲硅烷基酯（TMSC），并通过TMS转移过程继续调节链增长。考虑到NCA的多功能性以及利用C末端苯基硫代酯进行天然化学连接（NCL）的潜力，我们认为该方法可能提供一个强大的平台，能够快速生成功能性PAA及其C末端结合物，从而用于众多生物应用程序。
• Polypeptoids from <i>N</i>-Substituted Glycine <i>N</i>-Carboxyanhydrides: Hydrophilic, Hydrophobic, and Amphiphilic Polymers with Poisson Distribution
  作者：Corinna Fetsch、Arlett Grossmann、Lisa Holz、Jonas F. Nawroth、Robert Luxenhofer

  DOI：10.1021/ma201015y

  日期：2011.9.13

  Preparation of defined and functional polymers has been one of the hottest topics in polymer science and drug delivery in the recent decade. Also, research on (bio)degradable polymers gains more and more interest, in particular at the interface of these two disciplines. However, in the majority of cases, combination of definition, functionality and degradability, is problematic. Here we present the preparation and characterization (MALDI-ToF MS, NMR, GPC) of nonionic hydrophilic, hydrophobic, and amphiphilic N-substituted polyglycines (polypeptoids), which are expected to be main-chain degradable and are able to disperse a hydrophobic model compound in aqueous media. Polymerization kinetics suggest that the polymerization is well controlled with strictly linear pseudo first-order kinetic plots to high monomer consumption. Moreover, molar mass distributions of products are Poisson-type and molar mass can be controlled by the monomer to initiator ratio. The presented polymer platform is nonionic, backbone degradable, and synthetically highly flexible and may therefore be valuable for a broad range of applications, in particular as a biomaterial.