α-propargyl ε-caprolactone | 1239734-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: α-propargyl ε-caprolactone
• 英文别名: α-propargyl-ε-caprolactone；3-(prop-2-ynyl)oxepan-2-one；alpha-Propargyl-epsilon-caprolactone；3-prop-2-ynyloxepan-2-one
• CAS: 1239734-73-6
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: QSOZTJMZPZROSY-UHFFFAOYSA-N

物化性质

• 沸点：
  275.5±13.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-己内酯 、 3-溴丙炔 在 lithium diisopropyl amide 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以60%的产率得到α-propargyl ε-caprolactone
  参考文献：
  名称：

  MRI-VISIBLE HYDROPHOBIC COPOLYMER

  摘要：

  本发明涉及一种疏水性热塑性共聚物，特别适用于制造和/或涂层医疗器械，特别是可植入医疗器械。该共聚物通过共聚得到，并且包含至少一个第一单体单元和至少一个第二单体单元，该第二单体单元上嫁接有可以与该顺磁离子形成络合物的顺磁离子螯合配体，或者与该顺磁离子形成络合物的顺磁离子螯合配体，其中第二单体单元的嫁接量足够使共聚物在与所述顺磁离子形成络合物时在磁共振成像中可见。本发明还涉及一种获得该疏水性热塑性共聚物的方法。

  公开号：

  US20140302324A1

文献信息

• Cyclodextrin-Modified Polyesters from Lactones and from Bacteria: An Approach to New Drug Carrier Systems
  作者：Olga Jazkewitsch、Adam Mondrzyk、Rebecca Staffel、Helmut Ritter

  DOI：10.1021/ma1027627

  日期：2011.3.22

  Copper(I)-catalyzed cycloaddition of synthetic and bacterial copolyesters bearing pendant alkyne group with mono-(6-azido-6-desoxy)-β-cyclodextrin was carried out to synthesize β-CD-functionalized copolyester. The synthetic “clickable” copolyesters were obtained by the ring-opening copolymerization of the propargyl-modified lactones and ε-caprolactone. The bacterial copolyesters containing an alkyne

  进行了铜（I）催化的带有侧链炔基的合成和细菌共聚酯与单-（6-叠氮基-6-脱氧）-β-环糊精的环加成反应，合成了β-CD-官能化的共聚酯。通过炔丙基改性的内酯和ε-己内酯的开环共聚反应，得到合成的“可点击的”共聚酯。革兰氏阴性细菌油假单胞菌由10-十一碳烯酸和己酸的混合物生物合成含有炔基的细菌共聚酯。“点击”反应的修饰产物通过FT-IR，1 H NMR光谱和DSC表征。此外，通过动态光散射测量证明了共价连接的β-环糊精部分的宿主客体能力。
• Antimicrobial Hydantoin-grafted Poly(ε-caprolactone) by Ring-opening Polymerization and Click Chemistry
  作者：Licheng Tan、Samarendra Maji、Claudia Mattheis、Yiwang Chen、Seema Agarwal

  DOI：10.1002/mabi.201200238

  日期：2012.12

  ring‐opening polymerization and subsequently used to graft antibacterial hydantoin moieties via click chemistry by a copper(I)‐catalyzed azide‐alkyne cycloaddition reaction. The well‐controlled chemical structures of the grafted copolymers and its precursors are verified by FT‐IR spectroscopy, NMR spectroscopy, and GPC characterizations. According to the DSC and XRD results, the polymorphisms of these

  这项工作报道了新型可降解和抗菌的聚己内酯基聚合物。带有炔丙基侧基的聚酯是通过开环聚合成功制备的，随后通过铜（I）催化的叠氮化物-炔烃环加成反应，通过点击化学，将其用于接枝抗菌性乙内酰脲。通过FT-IR光谱，NMR光谱和GPC表征验证了接枝共聚物及其前体的化学结构得到良好控制。根据DSC和XRD结果，取决于接枝的乙内酰脲的量，这些接枝共聚物的多晶型从半结晶变为无定形。用枯草芽孢杆菌和两株大肠杆菌进行抗菌测定 并显示出快速的抗菌作用。
• Formation and Characterization of Inclusion Complexes of Alkyne Functionalized Poly(ε-caprolactone) with β-Cyclodextrin. Pseudo-Polyrotaxane-Based Supramolecular Organogels.
  作者：Olga Jazkewitsch、Helmut Ritter

  DOI：10.1021/ma102456n

  日期：2011.1.25

  beta-Cyclodextrin has been found to form pseudo-polyrotaxanes with propargyl functionalized poly(epsilon-caprolactone) in N,N-dimethylformamide. The formation of inclusion complexes was proven by H-1 NMR and FT-IR spectroscopy, SEC, dynamic light scattering (DLS), polarized optical microscopy and wide-angle X-ray diffraction (WAXD). Furthermore, supramolecular organogels based on the pseudo-polyratoxanes (PPR) were synthesized via 1,3-dipolar cycloaddition of propargyl functionalized poly(epsilon-caprolactone) and mono-(6-azido-6-desoxy)-beta-cyclodextrin. The swelling degree and rheological behavior of the PPR gels were investigated in dependence of the cross-linker content.
• MRI-Visible Poly(ε-caprolactone) with Controlled Contrast Agent Ratios for Enhanced Visualization in Temporary Imaging Applications
  作者：Sarah El Habnouni、Benjamin Nottelet、Vincent Darcos、Barbara Porsio、Laurent Lemaire、Florence Franconi、Xavier Garric、Jean Coudane

  DOI：10.1021/bm400978a

  日期：2013.10.14

  Hydrophobic macromolecular contrast agents (MMCAs) are highly desirable to provide safe and efficient magnetic resonance (MR) visibility to implantable medical devices. In this study, we report on the synthesis and evaluation of novel biodegradable poly(epsilon-caprolactone)-based MMCAs. Poly(alpha-propargyl-epsilon-caprolactone-co-epsilon-caprolactone)s containing 2, 5, and 10 mol % of propargyl groups have been prepared by ring-opening copolymerization of e-caprolactone and the corresponding propargylated lactone. In parallel, a diazido derivative of the clinically used diethylenetriaminepentaacetic acid (DTPA)/Gd3+ complex has been synthesized. Finally, MM-visible poly(e-caprolactone)s (PCLs) were obtained by the efficient click ligation of these compounds via a Cu-I-catalyzed [3 + 2] cycloaddition. ICP-MS analyses confirmed the efficient coupling of the complex on the PCL backbone with the MRI-visible PCLs containing 1.0, 2.6, and 3.6 wt % of Gd3+. The influence of the Gd3+ grafting density on the T-1 relaxation times and on the MM visibility of the novel biodegradable MMCAs was evaluated. Finally, their stability and cytocompatibility were assessed with regard to their potential as innovative MRI-visible biomaterials for biomedical applications.
• BLOCK COPOLYMERS OF LACTONES AND POLY(PROPYLENE FUMARATE)
  申请人：Becker, Matthew

  公开号：EP3577156B1

  公开（公告）日：2022-05-04