4-(2-hydroxyethyl)-1,3-dioxolan-2-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 4-(2-hydroxyethyl)-1,3-dioxolan-2-one
• 英文别名: 4-(hydroxyethyl)-1,3-dioxolan-2-one
• 化学式: C₅H₈O₄
• 分子量: 132.116
• InChiKey: ATUDGFIJODEJNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxyethyl)-1,3-dioxolan-2-one 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 四丁基氟化铵 、 乙酸酐 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 52.5h， 生成 N-(1-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-((2-(2-oxo-1,3-dioxolan-4-yl)ethoxy)methoxy)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide
  参考文献：
  名称：

  含有2'-o-烷氧基甲基的单体作为合成子通过磷酸三酯法合成寡核糖核苷酸的方法。

  摘要：

  已经开发了用于使用O-亲核分子内催化合成用于固相磷酸三酯寡核苷酸的2'-O-位含有烷氧基甲基的核糖核苷酸单体的通用方案。特别地，已经制备了包含2'-O-改性的2-叠氮基乙氧基甲基，炔丙基氧基甲基或3,4-环碳酸酯丁氧基甲基的单体。

  DOI：

  10.1134/s1068162011050025
• 作为产物：
  描述：

  4-(2-benzyloxy)ethyl-1,3-dioxolan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到4-(2-hydroxyethyl)-1,3-dioxolan-2-one
  参考文献：
  名称：

  Synthesis of diether-linked cationic lipids for gene delivery

  摘要：

  Quaternary ammonium lipids 1b-d, with diether linkages between hydrocarbon chains and butane or hexane backbone, were synthesized for cationic liposome-mediated gene delivery. The synthetic strategy of using C-4 or C-6 synthon permits the achievement of the variation of the hydrophobic domain as well as changes of space between the quaternary ammonium head and the hydrophobic domain in the diether-linked cationic lipids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00187-0

文献信息

• Zinc monoglycerolate as a catalyst for the conversion of 1,3- and higher diols to diurethanes
  作者：Sanjitha Kulasegaram、Uzma Shaheen、Terence W. Turney、Will P. Gates、Antonio F. Patti

  DOI：10.1039/c5ra05032d

  日期：——

  An efficient approach to the synthesis of diurethanes from 1,3- and higher diols (n ≥ 3) is described.

  一种从1,3-和更高的二醇（n ≥ 3）合成二尿酰胺的高效方法被描述。
• Palladium-Catalyzed Carbonylation of Diols to Cyclic Carbonates
  作者：David M. Pearson、Nicholas R. Conley、Robert M. Waymouth

  DOI：10.1002/adsc.201100240

  日期：2011.11

  affords cyclic carbonates. The oxidative carbonylation of diols proceeds under mild conditions, requiring only 1 atm of carbon monoxide, and produces cyclic carbonates in moderate to good yields. Both 1,2- and 1,3-diols can be carbonylated using (neocuproine)Pd(OAc)2 and sodium dichloroisocyanuric acid, which serves as a competent oxidant and base for this system, to yield 5- and 6-membered cyclic carbonates

  以N-氯代琥珀酰亚胺为底物，由（新癸胺）乙酸钯（II）（新丙氨酸= 2,9-二甲基-1,10-菲咯啉）或乙酸钯（II）/（-）-黄嘌呤催化1,2-二醇的烷氧基羰基化反应。氧化剂提供环状碳酸酯。二醇的氧化羰基化反应在温和的条件下进行，仅需1 atm一氧化碳，并以中等至良好的收率生产环状碳酸酯。1,2-二醇和1,3-二醇都可以使用（新oc碱）Pd（OAc）2和二氯异氰尿酸钠进行羰基化反应生成该5元和6元环状碳酸酯，后者是该体系的有效氧化剂和碱。 。
• Substrate-Controlled Product Divergence: Conversion of CO₂ into Heterocyclic Products
  作者：Jeroen Rintjema、Roel Epping、Giulia Fiorani、Eddy Martín、Eduardo C. Escudero-Adán、Arjan W. Kleij

  DOI：10.1002/anie.201511521

  日期：2016.3.14

  Substituted epoxy alcohols and amines allow substrate‐controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2‐derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions

  取代的环氧醇和胺可通过不同的机械歧管，将底物控制的CO 2转化为多种杂环结构。这种新方法通过胺或醇单元对CO 2的初始活化，导致了源自CO 2衍生产品的异常范围，从而在温和的反应条件下为分子内环氧开环提供了亲核试剂。对照实验通过遵循S N i途径的亲核试剂开环步骤和5-exo-tet环化作用，支持了胺/醇片段在该过程中的关键作用，从而形成了杂环骨架。
• Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups
  作者：Karolina M. Tomczyk、Piotr A. Guńka、Paweł G. Parzuchowski、Janusz Zachara、Gabriel Rokicki

  DOI：10.1039/c2gc35265f

  日期：——

  We report a new one-pot synthetic route to tetrahydrofuran derivatives, which were unexpectedly produced under basic conditions by intramolecular etherification of substituted five-membered cyclic carbonates. For alcohols with vicinal hydroxyl groups, and additional OH groups at the β-position, intramolecular etherification leading to 3-hydroxytetrahydrofuran derivatives was observed. These reactions

  我们报告了一种新的一锅合成路线到四氢呋喃衍生物，这是在基本条件下通过取代的五元环的分子内醚化意外产生的 碳酸盐。为了酒类由于具有邻位羟基，并且在β位具有额外的OH基，观察到分子内醚化导致3-羟基四氢呋喃衍生物。研究了每个分子中具有2至6个羟基的化合物的这些反应，并提出了机理。所开发的方法为五元合成提供了一种新的环保方法环醚 非酸性条件下的衍生物。
• Structure-property relationship and transport properties of structurally related silyl carbonate electrolytes
  作者：Manuela Philipp、Rajesh Bhandary、Florian J. Groche、Monika Schönhoff、Bernhard Rieger

  DOI：10.1016/j.electacta.2015.05.108

  日期：2015.8

  Ten different substituted structurally related linear and cyclic carbonates were synthesized and investigated as electrolyte solvents for lithium-ion cells. Synthesis of the compounds, mainly silyl carbonates, was carried out via catalytic CO2 addition, nucleophilic substitution or hydrosilylation. Besides the ten synthesized compounds a binary mixture of a cyclic and linear silyl carbonate, propylene carbonate (PC), diethyl carbonate (DEC) and a binary mixture thereof were analyzed as a function of molar lithium ((bistrifluoromethyl) sulfonyl) imide LiTFSI ratio in order to develop a structure-property relationship. The extrapolation of the temperature-dependent ionic conductivities using Vogel-Tamman-Fulcher (VTF) equation revealed a solvent assisted ionic transport mechanism. The strength of interaction between the lithium-ion and the respective carbonates was investigated via C-13 and Si-29 NMR measurements by the change of the chemical shift upon LiTFSI addition. The results show that the interaction of the lithium ion with the cyclic carbonates is much stronger compared to the linear ones and varies among the different substituents. These findings were in good accordance with ionicities represented by the Walden product. The diffusivities of Li+ and TFSI were determined via Pulsed Field Gradient STimulated Echo (PGSTE)-NMR. The hydrodynamic radii calculated thereof demonstrate the superior coordination ability of the cyclic carbonates as compared to linear structures. Furthermore, Haven ratios indicate rather different dissociation abilities of different carbonate solvents, depending on the structural fragment of the solvents. (C)2015 Elsevier Ltd. All rights reserved.