N-(allyloxy)carbonylhomocysteine thiolactone | 1261160-46-6

• 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: N-(allyloxy)carbonylhomocysteine thiolactone
• 英文别名: prop-2-enyl N-(2-oxothiolan-3-yl)carbamate
• CAS: 1261160-46-6
• 化学式: C₈H₁₁NO₃S
• mdl: MFCD24389339
• 分子量: 201.246
• InChiKey: HDMBOOUTYLRJFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  DL-高半胱氨酸硫内酯盐酸盐 、 氯甲酸烯丙酯 在 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 以96.7%的产率得到N-(allyloxy)carbonylhomocysteine thiolactone
  参考文献：
  名称：

  硫代内酯结构单元的合成作为可持续功能材料的潜在前体

  摘要：

  使用简单的化学路线合成了来自同型半胱氨酸硫代内酯和硫代对苯二酸的多功能单体库。已开发出通用方案，可产生多克数量的目标化合物，并能够在功能性涂料领域进行有希望的化合物的放大实验。选择靶标和合成途径时考虑的方面包括功能多样性，预期的物理性质，试剂的可持续性和商业可用性以及实现与工业相关的过程的可行性。在产率，物理性质和化学行为方面观察到趋势。

  DOI：

  10.1016/j.tet.2016.08.076

文献信息

• Two tandem multicomponent reactions for the synthesis of sequence-defined polymers
  作者：Lu Yang、Ze Zhang、Bofei Cheng、Yezi You、Decheng Wu、Chunyan Hong

  DOI：10.1007/s11426-015-5448-0

  日期：2015.11

  Multicomponent polymerizations have become powerful tools for the construction of sequence-defined polymers. Although the Passerini multicomponent reaction has been widely used in the synthesis of sequence-defined polymers, the tandem usage of the Passerini multicomponent reaction and other multicomponent reactions in one-pot for the synthesis of sequence-defined polymers has not been developed until now. In this contribution, we report the tandem usage of the Passerini three-component reaction and the three-component amine-thiol-ene conjugation reaction in one pot for the synthesis of sequence-defined polymers. The Passerini reaction between methacrylic acid, adipaldehyde, and 2-isocyanobutanoate was carried out, affording a new molecule containing two alkene units. Subsequently, an amine and a thiolactone were added to the reaction system, whereupon the three-component amine-thiol-ene conjugating reaction occurred to yield a sequence-defined polymer. This method offers more rapid access to sequence-defined polymers with high molecular diversity and complexity.

  多组分聚合已成为构建序列定义聚合物的强大工具。尽管Passerini多组分反应已广泛应用于序列定义聚合物的合成，但迄今为止，在一锅中联用Passerini多组分反应和其他多组分反应来合成序列定义聚合物尚未得到发展。在此项研究中，我们报告了在一锅中联用Passerini三组分反应和三组分胺-硫醇-烯结合反应来合成序列定义聚合物。我们进行了以甲基丙烯酸、戊醛和2-异氰基丁酸酯为反应物的Passerini反应，产物为含有两个烯键单元的新分子。随后，向反应体系中加入了一种胺和一种硫内酯，随后发生了三组分胺-硫醇-烯结合反应，产生了序列定义聚合物。这种方法提供了更快速获得高分子多样性和复杂性的序列定义聚合物的途径。
• One-Pot Multistep Reactions Based on Thiolactones: Extending the Realm of Thiol−Ene Chemistry in Polymer Synthesis
  作者：Pieter Espeel、Fabienne Goethals、Filip E. Du Prez

  DOI：10.1021/ja1098098

  日期：2011.2.16

  The in situ generation of thiols by nucleophilic ring-opening of a thiolactone with amines, followed by a UV-initiated radical thiol-ene reaction in a one-pot fashion, has been evaluated as an accelerated and versatile protocol for the synthesis of several types of polymeric architectures. After elaboration of a model amine-thiol-ene conjugation reaction, a number of routes based on readily available thiolactone-containing structures have been developed to successfully assemble functional, linear polymers and networks via a mild and facile radical photopolymerization process.
• Synthesis of thiolactone building blocks as potential precursors for sustainable functional materials
  作者：Daniel Frank、Pieter Espeel、Sven Claessens、Edwin Mes、Filip E. Du Prez

  DOI：10.1016/j.tet.2016.08.076

  日期：2016.10

  to multi-gram amounts of the targeted compounds and enabling up-scaling experiments for promising compounds in the area of functional coatings. Aspects considered during selection of targets and synthesis pathways included functional diversity, expected physical properties, sustainability and commercial availability of reagents, as well as feasibility to achieve an industrially relevant process. Trends

  使用简单的化学路线合成了来自同型半胱氨酸硫代内酯和硫代对苯二酸的多功能单体库。已开发出通用方案，可产生多克数量的目标化合物，并能够在功能性涂料领域进行有希望的化合物的放大实验。选择靶标和合成途径时考虑的方面包括功能多样性，预期的物理性质，试剂的可持续性和商业可用性以及实现与工业相关的过程的可行性。在产率，物理性质和化学行为方面观察到趋势。