(4S,5S)-2-oxo[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

• 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: (4S,5S)-2-oxo[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester
• 英文别名: (4S,5S)-diethyl 2-oxo-1,3-dioxolane-4,5-dicarboxylate；diethyl (4S,5S)-2-oxo-1,3-dioxolane-4,5-dicarboxylate
• 化学式: C₉H₁₂O₇
• 分子量: 232.19
• InChiKey: KSWKOGWHUDSCFD-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  D-(-)-酒石酸二乙酯 、 氯甲酸三氯甲酯 在 甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 120.0h， 以90%的产率得到(4S,5S)-2-oxo[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Remarkably Efficient Charcoal-Promoted Ring-Closing Carbonylations

  摘要：

  实现了一种高效、多功能且实用的克级氧杂氮环、咪唑氮环和二氧烷酮的制备。

  DOI：

  10.1055/s-2006-926340

文献信息

• Diphenyl Carbonate: A Highly Reactive and Green Carbonyl Source for the Synthesis of Cyclic Carbonates
  作者：Ek Raj Baral、Jun Hee Lee、Jeung Gon Kim

  DOI：10.1021/acs.joc.8b01695

  日期：2018.10.5

  A practical, safe, and highly efficient carbonylation system involving a diphenyl carbonate, an organocatalyst, and various diols is presented herein and produces highly valuable cyclic carbonates. In reactions with a wide range of diols, diphenyl carbonate was activated by bicyclic guanidine 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a catalyst, which successfully replaced highly toxic and unstable

  本文提出了一种实用，安全且高效的羰基化系统，该系统涉及碳酸二苯酯，有机催化剂和各种二醇，并可以生产出有价值的环状碳酸酯。在与各种二醇的反应中，碳酸二苯酯被双环胍1,5,7-三氮杂双环[4.4.0] dec-5-ene（TBD）用作催化剂，成功取代了剧毒和不稳定的光气或其衍生物，同时保持所需的高反应活性。而且，该新系统可用于合成空间需求的环状碳酸酯，例如四取代的频哪醇碳酸酯，而这些碳酸酯是无法通过其他常规方法获得的。
• Stereochemical Divergence in the Formation of Organic Carbonates Derived from Internal Epoxides
  作者：Christopher J. Whiteoak、Eddy Martin、Eduardo Escudero-Adán、Arjan W. Kleij

  DOI：10.1002/adsc.201201070

  日期：2013.8.12

  AbstractCatalysis of the challenging cycloaddition of carbon dioxide to internal epoxides has been studied using iron(III) amine triphenolate complexes and particular focus has been given to the stereochemical regulation of this process. When pure cis‐ or trans‐2,3‐epoxybutane is used as substrate, the stereochemistry of the product can be controlled yielding selectively cis‐ or trans‐cyclic carbonates for both epoxidic substrates. This stereochemical divergence relates to two accessible catalytic pathways leading to either the cis or trans product via two distinct ring‐closure steps. The involved mechanism and stereocontrol is a function of the catalyst/co‐catalyst loading, and is further influenced by the medium, temperature and catalyst/co‐catalyst structure. Other trans‐internal epoxides could also be successfully converted into the pure trans‐cyclic carbonate products without any loss of stereochemical information.magnified image
• Remarkably Efficient Charcoal-Promoted Ring-Closing Carbonylations
  作者：Emmanuel Vrancken、Nacira Alouane、Audrey Boutier、Cyriella Baron、Pierre Mangeney

  DOI：10.1055/s-2006-926340

  日期：——

  An efficient, versatile and practical gram-scale preparation of oxazolidinone, imidazolidinone and dioxolanone is achieved.

  实现了一种高效、多功能且实用的克级氧杂氮环、咪唑氮环和二氧烷酮的制备。