methacryloyl-trans-4-hydroxyproline | 1170354-78-5

• 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-trans-4-hydroxyproline
• 英文别名: prolinyl methacrylate；(2S,4R)-4-(2-methylprop-2-enoyloxy)pyrrolidine-2-carboxylic acid
• CAS: 1170354-78-5
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: IOXCOUDRCFEERB-RQJHMYQMSA-N

物化性质

• 沸点：
  340.9±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-羟基脯氨酸 、 甲基丙烯酰氯 在 三氟乙酸 、 对甲苯磺酸 作用下， 以67%的产率得到methacryloyl-trans-4-hydroxyproline
  参考文献：
  名称：

  基于产物印迹聚合物的用于醛醇缩合反应的两亲性和可光转换的有机催化剂

  摘要：

  使用双功能单体制备了一系列包含疏水性光敏位点和亲水性催化活性位点的两亲分子印迹聚合物（MIP1，MIP2，MIP3，MIP4，MIP5和MIP6）。这些聚合物的特征在于扫描电子显微镜，N 2吸附-解吸分析，傅立叶变换红外光谱，热重量分析和紫外可见光谱。在室温下，在DMSO和水的混合溶剂中，研究了两亲分子印迹聚合物对对硝基醛和丙酮之间的羟醛反应（分子扩大反应）的催化活性。聚合物催化剂MIP3表现最佳，并且在低催化剂负载量（5摩尔％关于醛的1-羟基脯氨酸）和光开关特性（光调节的转化率差异为20％）。与相应的非印迹聚合物相比，当将分子印迹聚合物用作催化剂时，可以获得更高的结合能力，更高的转化率和更好的光开关性能，这说明了分子印迹聚合物中特定空腔的重要性。

  DOI：

  10.1016/j.mcat.2017.07.022

文献信息

• METHOD OF PRODUCING OPTICALLY ACTIVE ß-AMINOCARBONYL COMPOUND
  申请人：DEXERIALS CORPORATION

  公开号：US20160159729A1

  公开（公告）日：2016-06-09

  In a method of producing an optically active β-aminocarbonyl compound using a column reactor, a column for a column reactor is charged with asymmetric catalyst particles to form a column reactor. Compounds for a Mannich-type reaction are introduced into the column reactor to be brought into contact with the asymmetric catalyst particles, to thereby convert the compounds to an optically active β-aminocarbonyl compound. The preferable asymmetric catalyst particles are resin particles that are prepared from a monomer composition containing a proline derivative monomer having an unsaturated bond and a radical polymerization initiator, and that act as a catalyst for an asymmetric Mannich-type reaction.

  在使用柱式反应器生产光学活性β-氨基羰基化合物的方法中，将柱式反应器的柱子充填有不对称催化剂颗粒，形成柱式反应器。将用于Mannich反应的化合物引入柱式反应器，使其与不对称催化剂颗粒接触，从而将化合物转化为光学活性β-氨基羰基化合物。优选的不对称催化剂颗粒是由含有脯氨酸衍生物单体和自由基聚合引发剂的单体组成的树脂颗粒，可作为Mannich反应的不对称催化剂。
• Aldol reactions catalyzed by l-proline functionalized polymeric nanoreactors in water
  作者：Annhelen Lu、Pepa Cotanda、Joseph P. Patterson、Deborah A. Longbottom、Rachel K. O'Reilly

  DOI：10.1039/c2cc35170f

  日期：——

  The use of functional core–shell micelles as asymmetric catalytic nanoreactors for organic reactions in water is presented. An unprecedented increase in rate of reaction was achieved, which is proposed to be associated with the ability of the nanostructures to effectively concentrate the reagents in the catalytically active micelle core.

  本文介绍了如何利用功能性核壳胶束作为不对称催化纳米反应器，在水中进行有机反应。反应速率得到了前所未有的提高，这可能与纳米结构能够有效地将试剂集中在具有催化活性的胶束核心有关。
• POLYMER ORGANOCATALYST AND PREPARATION PROCESS
  申请人：Hansen Tore

  公开号：US20110034654A1

  公开（公告）日：2011-02-10

  A chiral polymer organocatalyst comprising a main chain and side chain organocatalytic groups covalently attached to the main chain, which organocatalytic groups comprise an amino acid or amino acid derivative of the following general formula (I), in which one stereoisomeric form predominates: formula (I) wherein the catalyst is bound to the polymer main chain via R 1 , R 2 , R 4 , R 5 or R 6 through a linker (L) or direct bond, and wherein R 1 -R 6 and Z are defined as follows: R 1 is H, a naturally occurring alpha-amino acid side chain or a non-natural commercially available alpha-amino acid side chain that may contain L; R 2 is H, O (doubly bonded to give a carbonyl), O-L (where L is a linker), NH-L or L; R 3 is H or doubly bonded to give a carbonyl with R 2 when R 2 is O; R 4 is H, C 1 -C 6 alkyl or L R 5 is H, CO 2 H, C 1 -C 6 alkyl, benzyl, L, CONHR (in which R is alkyl, aryl, heteroaryl, arylalkyl or, heteroarylalkyl), tetrazolyl, CH2 coupled to a triazole moiety, an esterified CH 2 OH or CO 2 R (in which R is alkyl, aryl, heteroaryl, arylalkyl N or heteroarylalkyl), formula (II) or formula (III) wherein z is formula (IV) or a directed bond, X 4 is H, Me 3 Si or Et 3 Si, X 3 comprises a naturally-occurring alpha-amino acid side chain, H, C 1 -C 6 alkyl or phenyl, Ar 1 and Ar 2 are each independently aryl or heteroaryl, and Y denotes the position of attachment to the main chain or linker; and R 6 is H, CO 2 H3 C 1 -C 6 alkyl, benzyl or L; and wherein the polymer organocatalyst comprises a cross-linked polymer.

  手性聚合物有机催化剂，包括主链和侧链有机催化基团，这些有机催化基团通过共价键连接到主链上，其中所述有机催化基团包括以下通式（I）的氨基酸或氨基酸衍生物，其中一种立体异构体占优势：通式（I），其中催化剂通过连接物（L）或直接键与聚合物主链通过R1、R2、R4、R5或R6结合，其中R1-R6和Z的定义如下：R1为H，天然存在的α-氨基酸侧链或非天然商业可得的α-氨基酸侧链，可能包含L；R2为H，O（双键形成羰基），O-L（其中L为连接物），NH-L或L；当R2为O时，R3为H或与R2形成双键形成羰基；R4为H，C1-C6烷基或L；R5为H，CO2H，C1-C6烷基，苄基，L，CONHR（其中R为烷基、芳基、杂芳基、芳基烷基或杂芳基烷基），四唑基，与三唑基结合的CH2，酯化的CH2OH或CO2R（其中R为烷基、芳基、杂芳基、芳基烷基、N或杂芳基烷基），通式（II）或通式（III），其中z为通式（IV）或直接键，X4为H、Me3Si或Et3Si，X3包括天然存在的α-氨基酸侧链、H、C1-C6烷基或苯基，Ar1和Ar2各自独立地为芳基或杂芳基，Y表示与主链或连接物的连接位置；R6为H、CO2H、C1-C6烷基、苄基或L；聚合物有机催化剂包括交联聚合物。
• Proline-based polymeric monoliths: Synthesis, characterization, and applications as organocatalysts in aldol reaction
  作者：Dipti Garg、J.-H. Ahn、Ghanshyam S. Chauhan

  DOI：10.1002/pola.23845

  日期：2010.3.1

  and nitrogen analysis and used as catalyst in aldol reactions. The swelling behavior of the monolith was also studied as function of various external parameters like pH and temperature. The monoliths synthesized with 1% crosslinker was selected as candidate monolith for use as catalyst in aldol reaction, which was studied as a function of time, temperature, substrate structure, and amount of water:EtOH

  基于脯氨酸的聚合物整料是通过绿色协议使用脂肪酶催化的甲基丙烯酸和4-羟基脯氨酸的酯化反应合成的。将由此制备的甲基丙烯酸脯氨酯原位聚合为交联的整料。整料通过多种技术进行表征，例如傅立叶红外光谱，1 H-NMR，13C-NMR，扫描电子显微镜（SEM），X射线衍射（XRD）和氮分析，并用作醇醛反应中的催化剂。还研究了整料的溶胀行为，该溶胀行为是随各种外部参数（例如pH和温度）而变化的。选择由1％交联剂合成的整体材料作为在醇醛反应中用作催化剂的候选整体材料，研究该整体材料是时间，温度，底物结构和水：EtOH量的函数。催化剂在交联的醇醛缩合反应中表现出高效率，特别是在具有吸电子取代基的芳族底物的情况下，当研究多达五个循环的可循环性时，还观察到良好的活性保持性。©2010 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem 48：1007–1015，2010年
• METHOD OF PRODUCING OPTICALLY ACTIVE COMPOUND
  申请人：DEXERIALS CORPORATION

  公开号：US20160250625A1

  公开（公告）日：2016-09-01

  An optically active compound production method using a column reactor, a column for column reactor is charged with asymmetric catalyst particles to produce the column reactor, and reaction compound is introduced into column reactor to bring reaction compound into contact with asymmetric catalyst particles, whereby reaction compound is converted to optically active compound. Asymmetric catalyst particles are preferably resin particles that are prepared from a monomer composition containing a proline derivative monomer having unsaturated bond and radical polymerization initiator and serve as catalyst for enamine mechanism reaction. Asymmetric catalyst particles are preferably resin particles prepared by micro-channel method including injecting monomer composition into continuous phase to thereby form droplets of monomer composition in continuous phase and then heating droplets to cause proline derivative monomer having an unsaturated bond to undergo radical polymerization.