ethyl (2-hydroxyethyl) fumarate | 3207-19-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2-hydroxyethyl) fumarate
• 英文别名: ethyl 2-hydroxyethyl fumarate；2-Butenedioic acid (2E)-, ethyl 2-hydroxyethyl ester；1-O-ethyl 4-O-(2-hydroxyethyl) (E)-but-2-enedioate
• CAS: 3207-19-0
• 化学式: C₈H₁₂O₅
• mdl: MFCD30479325
• 分子量: 188.18
• InChiKey: BGUIZQYQWQACDW-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2-hydroxyethyl) fumarate 在 咪唑 、 碘 、 二氯乙基铝 、 三苯基膦 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 生成 (1R^*,2R^*,3S^*,6R^*)-1-ethyl 2-(2-iodoethyl) bicyclo[2.2.1]hept-4-ene-1,2-dicarboxylate
  参考文献：
  名称：

  Selective complexation of 2-hydroxyethyl esters using lewis acids

  摘要：

  Competitive Diels-Alder reactions between ethyl acrylate and 2-hydroxyethyl acrylate (1,3-cyclopentadiene, CH2Cl2, 0 degrees C) in the presence of a variety of Lewis acids indicate that selective complexation of the 2-hydroxyethyl ester can be accomplished, most notably using EtAlCl2. Further Diels-Alder reactions using ethyl 2-hydroxyethyl fumarate support these findings. C-13 NMR studies provide direct evidence for the nature of the interactions between 2-hydroxyethyl esters and EtAlCl2. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01051-5
• 作为产物：
  描述：

  富马酸单乙酯 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 ethyl (2-hydroxyethyl) fumarate
  参考文献：
  名称：

  竞争性狄尔斯-阿尔德反应为机理探针的2-羟乙基酯的选择性路易斯酸络合

  摘要：

  竞争性Diels –涉及丙烯酸乙酯，丙烯酸2-羟乙酯和丙烯酸2-甲氧基乙酯的Alder反应表明，某些路易斯酸（例如EtAlCl 2）选择性地与2-羟乙基酯基团络合。使用2-羟基乙基富马酸乙酯的研究支持了这些发现。13 C NMR光谱学提供了一些有关2-羟乙基酯与EtAlCl 2之间相互作用的性质的证据。描述了EtAlCl 2对（2 R ∗，3 R ∗）-2-（3-羟基）丙烯酸丁酯的Diels-Alder反应中非对映控制水平的影响。

  DOI：

  10.1016/s0040-4020(99)01071-6

文献信息

• Protection‐Group‐Free Synthesis of Sequence‐Defined Macromolecules via Precision λ‐Orthogonal Photochemistry
  作者：Waldemar Konrad、Christian Fengler、Sarrah Putwa、Christopher Barner‐Kowollik

  DOI：10.1002/anie.201901933

  日期：2019.5.20

  acid and a fumarate. Both light‐induced chain growth reactions are carried out in a λ‐orthogonal fashion, exciting the respective photosensitive group selectively and thus avoiding protecting chemistry. Characterization of each sequence‐defined chain (size‐exclusion chromatography (SEC), high‐resolution electrospray ionization mass spectrometry (ESI‐MS), and NMR spectroscopy), confirms the precision

  提出了一种通过独特的光化学方案将单分散序列定义的线性大分子转化为光的先进方法，该方法不需要任何保护基化学作用。从对称的核心单元开始，通过两单体系统可得到分子量高达6257.10 g mol -1的精密大分子：一个带有unit官能化的可见光响应性四唑和光笼化的UV响应性二烯的单体单元，可实现链增长的迭代方法；单体单元，其配备有羧酸和富马酸酯。两种光诱导的链增长反应均在λ中进行正交方式，有选择地激发相应的光敏基团，从而避免保护化学物质。每个序列定义链的表征（尺寸排阻色谱法（SEC），高分辨率电喷雾电离质谱法（ESI-MS）和NMR光谱法）证实了大分子的精密性。
• A facile route to segmented copolymers by fusing ambient temperature step-growth and RAFT polymerization
  作者：Thomas Gegenhuber、Alexander M. Schenzel、Anja S. Goldmann、Per B. Zetterlund、Christopher Barner-Kowollik

  DOI：10.1039/c7cc06347d

  日期：——

  WWe introduce the synthesis of segmented copolymers via a catalyst-free Diels-Alder (DA) reaction at ambient temperature via step-growth (SG) polymerization and subsequent RAFT polymerization. High molecular weight SG polymers are readily obtained (Mw = 40,000 g∙mol-1), featuring trithiocarbonate groups in their lateral chain, which allow rapid monomer insertion via reversible addition fragmentation

  我们在环境温度下通过无步增长（SG）聚合和随后的RAFT聚合，通过无催化剂的Diels-Alder（DA）反应引入链段共聚物的合成。容易获得高分子量SG聚合物（M w = 40,000 g∙mol -1），其侧链具有三硫代碳酸酯基团，可通过可逆加成断裂链转移（RAFT）聚合反应快速插入单体。
• SOLUBLE BRANCHED POLYMERS
  申请人：Grigoras Cristian

  公开号：US20140303313A1

  公开（公告）日：2014-10-09

  Branched polymers are prepared from at least (A) at least one monomer having an electron donor moiety, (B) at least one monomer having an electron acceptor moiety, and (C) at least one multifunctional branching agent comprising a urea moiety and at least two N-vinyl groups. The branched polymers are least 20% (by weight) soluble in a solvent for which the corresponding polymer of equal molecular weight made without said multifunctional branching agent is at least 20% (by weight) soluble. Due in part to the wide range of chemistries and solubility and rheological properties, the branched polymers find application in personal care, pharmaceutical/nutritional, and performance chemicals compositions.

  分支聚合物由至少（A）至少一种具有电子给体基团的单体，（B）至少一种具有电子受体基团的单体和（C）至少一种多功能分支剂组成，该分支剂包含尿素基团和至少两个N-乙烯基团。这些分支聚合物在相应的等分子量聚合物不含多功能分支剂的溶剂中至少有20％（重量）的溶解度，由于其广泛的化学性质、溶解度和流变性质，这些分支聚合物在个人护理、制药/营养和性能化学成分中应用广泛。
• Complexes of the Gilman Reagent with Double Bonds across the π–σ Continuum
  作者：Steven H. Bertz、Stephen K. Cope、Richard A. Hardin、Michael D. Murphy、Craig A. Ogle、David T. Smith、Andy A. Thomas、Tara N. Whaley

  DOI：10.1021/om300622c

  日期：2012.11.26

  By using rapid injection NMR at low temperatures, a variety of pi-complexes of lithium dimethylcuprate(I) with C-C, C-N, and C-S double bonds have been prepared and characterized. Complexation is generally accompanied by large upfield changes in chemical shift for the substrate carbon atoms bonded to copper. In the case of alpha,beta-unsaturated carbonyl compounds, the changes for the carbonyl carbons are much smaller in magnitude, which is consistent with the usual eta(2) representation of these structures. It is possible for one ligand to displace another, and in this way an order of stability can be elucidated. Treatment of selected pi-complexes with chlorosilanes or cyanosilanes gives Cu-III intermediates.
• US4055518A
  申请人：——

  公开号：US4055518A

  公开（公告）日：1977-10-25