methacryloyl-L-lactic acid | 169233-07-2

• 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: methacryloyl-L-lactic acid
• 英文别名: (S)-(-)-methacryloyl-L-lactic acid；2-Propenoic acid, 2-methyl-, (1S)-1-carboxyethyl ester；(2S)-2-(2-methylprop-2-enoyloxy)propanoic acid
• CAS: 169233-07-2
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: MUWOTPLDXQSGQZ-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methacryloyl-L-lactic acid 在 2,6-二叔丁基-4-甲基苯酚 、 DPTS 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Synthesis and photoresponsive behavior of optically active methacrylic homopolymers containing side-chain spiropyran chromophores

  摘要：

  Novel optically-active methacrylic homopolymers bearing in the side chain one or more chiral groups of one single configuration (based on the L.-lactic acid residue) linked to the spiropyran chromophore, have been successfully synthesized and fully characterized.These intrinsically chiral polymers exhibit remarkable thermal stability, with glass transition temperatures in the range 100-130 degrees C and decomposition temperatures around 270 degrees C. The chiroptical characterization indicates the occurrence of asymmetric induction on the electronic transitions of the side-chain chromophore related to the number of L-lactic acid residues interposed between the main chain and the spiropyran chromophore.In the presence of acid, these systems can be used to modulate the protonation of polymeric azopyridine moieties upon photoisomerization of the spiropyran group. In addition to UV-Vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, the system thus behaving as a chiroptical switch. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.reactfunctpolym.2012.04.011

文献信息

• Supramolecular Chirality and Reversible Chiroptical Switching in New Chiral Liquid-Crystal Azopolymers
  作者：Joaquín Barberá、Loris Giorgini、Fabio Paris、Elisabetta Salatelli、Rosa M. Tejedor、Luigi Angiolini

  DOI：10.1002/chem.200801246

  日期：2008.12.8

  achieved by atom transfer radical polymerisation (ATRP) of a new optically active monomer (S)-4-[6-(2-methacryloyloxypropanoyloxy)hexyloxy)]-4'-ethoxyazobenzene [(S)-ML6A], containing the L-lactic residue of one absolute configuration in the side-chain. All the obtained polymeric samples, characterised by differential scanning calorimetry (DSC), X-ray diffraction (XRD) and polarised optical microscopy

  通过一种新型旋光单体的原子转移自由基聚合（ATRP）合成了具有良好控制结构（线性和三臂星形），平均链长明显且多分散性低的手性液晶聚合物-4- [6-（2-（甲基丙烯酸丙烯酰氧基丙酰氧基）己氧基）]-4'-乙氧基偶氮苯[（S）-ML6A]，在侧链中含有一个绝对构型的L-乳酸残基。以差示扫描量热法（DSC），X射线衍射（XRD）和偏振光学显微镜（POM）为特征的所有获得的聚合物样品均表现出近晶A（1/2）（完全相互交叉）液晶相并具有高清洁度转变温度取决于平均聚合度和大分子结构。由L-乳酸残基的不对称官能团在分子水平上引发的手性为聚合物提供了近乎均相的构象，在近晶相中具有与存在的H-聚集体有关的主要手性，该H-聚集体具有一个主要螺杆的构象不对称性-感觉。通过用圆偏振光（CPL）照射，可以光调制这些本征手性聚合物薄膜的手性。在用左手CPL（1-CPL）辐照后，薄膜的圆二色性（CD）光谱显示出椭圆度
• Novel optically active methacrylic polymers containing side-chain porphyrin moieties for chiral recognition
  作者：Luigi Angiolini、Tiziana Benelli、Loris Giorgini

  DOI：10.1016/j.polymer.2011.04.055

  日期：2011.6

  Novel optically active methacrylic homopolymers bearing in the side chain one or more chiral groups of one single configuration (l-lactic acid residue) linked to tetraphenylporphyrin have been successfully synthesized and fully characterized. These intrinsically chiral polymers exhibit remarkable thermal stability, with glass transition temperature in the range 250–315 °C and decomposition temperatures

  已成功合成并充分表征了在侧链上带有一个或多个与四苯基卟啉连接的单一构型（1-乳酸残基）的手性基团的新型光学活性甲基丙烯酸均聚物。 这些固有的手性聚合物具有出色的热稳定性，玻璃化转变温度在250-315°C范围内，分解温度在360-390°C范围内。光谱学，热学和手性表征表明，至少对于大分子的链段，在侧链部分之间存在偶极相互作用，并且存在手性螺旋构象。 所得大分子锌卟啉材料能够通过氮/锌配位键合旋光性α，ω-二胺客体，形成具有激子耦合双符号二向色性（CD）光谱的复合物，其符号与客体化合物的绝对构型有关。该行为是由于形成非对映体复合物，其至少对于链段而言导致优选的卟啉螺旋度。该方法非常灵敏，只需要几微克的客体化合物。
• Attachment of compounds to polymeric particles using dication ethers and a kit containing same
  申请人：Johnson & Johnson Clinical Diagnostics, Inc.

  公开号：EP0411711A2

  公开（公告）日：1991-02-06

  A method for attaching a reactive amine- or sulfhydryl-containing compound to polymeric particles using dication ether salts is disclosed.

  本发明公开了一种使用双阳离子醚盐将含反应性胺或巯基化合物附着到聚合物颗粒上的方法。
• Use of 1-(1-pyrrolidinylcarbonyl)pyridinium salts to attach compounds to caboxylated particles & a kit containing same
  申请人：Johnson & Johnson Clinical Diagnostics, Inc.

  公开号：EP0462670A1

  公开（公告）日：1991-12-27

  Useful materials for diagnostic tests, affinity chromatography, enzymatic reactions and immunoassays are prepared by covalently attaching reactive compounds containing reactive amino or sulfhydryl groups to polymeric particles having pendant carboxyl groups on the outer surfaces. Such reactive compounds include biologically reactive species, including enzymes, polypeptides and proteins. This attachment is carried out using specific carbamoylonium compounds, namely certain 1-(1-pyrrolidinylcarbonyl)pyridinium salts. These compounds react with the carboxyl groups on the particles to form intermediate reactive groups which then react with the amino or sulfhydryl groups to form a covalent linkage between particle and reactive compound. A kit comprises polymeric particles having carboxyl groups on the outer surfaces, and a 1-(1-pyrrolidinylcarbonyl)-pyridinium salt.

  通过将含有活性氨基或巯基的活性化合物共价连接到外表面具有悬垂羧基的聚合物颗粒上，可以制备出用于诊断测试、亲和层析、酶反应和免疫测定的有用材料。这类活性化合物包括生物活性物质，包括酶、多肽和蛋白质。这种附着是使用特定的氨基甲酰基化合物，即某些 1-（1-吡咯烷基羰基）吡啶鎓盐进行的。这些化合物与微粒上的羧基反应，形成中间反应基团，然后与氨基或巯基反应，在微粒和反应化合物之间形成共价连接。试剂盒包括外表面带有羧基的聚合物颗粒和 1-（1-吡咯烷基羰基）-吡啶鎓盐。
• Synthesis and photoresponsive behavior of optically active methacrylic homopolymers containing side-chain spiropyran chromophores
  作者：Luigi Angiolini、Tiziana Benelli、Erika Bicciocchi、Loris Giorgini、Françisco M. Raymo

  DOI：10.1016/j.reactfunctpolym.2012.04.011

  日期：2012.7

  Novel optically-active methacrylic homopolymers bearing in the side chain one or more chiral groups of one single configuration (based on the L.-lactic acid residue) linked to the spiropyran chromophore, have been successfully synthesized and fully characterized.These intrinsically chiral polymers exhibit remarkable thermal stability, with glass transition temperatures in the range 100-130 degrees C and decomposition temperatures around 270 degrees C. The chiroptical characterization indicates the occurrence of asymmetric induction on the electronic transitions of the side-chain chromophore related to the number of L-lactic acid residues interposed between the main chain and the spiropyran chromophore.In the presence of acid, these systems can be used to modulate the protonation of polymeric azopyridine moieties upon photoisomerization of the spiropyran group. In addition to UV-Vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, the system thus behaving as a chiroptical switch. (C) 2012 Elsevier Ltd. All rights reserved.