4-hydroxybutyl levulinate | 616236-44-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 4-hydroxybutyl levulinate
• 英文别名: 4-Hydroxybutyl 4-oxopentanoate
• CAS: 616236-44-3
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: SFBKVFWCYNTWSU-UHFFFAOYSA-N

物化性质

• 沸点：
  308.6±22.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxybutyl levulinate 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 4-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxybutyl 4-oxopentanoate
  参考文献：
  名称：

  Solid-Phase Synthesis of Thermolytic DNA Oligonucleotides Functionalized with a Single 4-Hydroxy-1-butyl or 4-Phosphato-/Thiophosphato-1-butyl Thiophosphate Protecting Group

  摘要：

  Several thermolytic CpG-containing DNA oligonucleotides analogous to 1 have been synthesized to serve as potential immunotherapeutic oligonucleotide prodrug formulations for the treatment of infectious diseases in animal models. Specifically, the CpG motif (GACGTT) of each DNA oligonucleotide has been functionalized with either the thermolabile 4-hydroxy-1-butyl or the 4-phosphato-/thiophosphato-1-butyl thiophosphate protecting group. This functionalization was achieved through incorporation of activated deoxyribonucleoside phosphoramidite 8b into the oligonucleotide chain during solid-phase synthesis and, optionally, through subsequent phosphorylation effected by phosphoramidite 9. Complete conversion of CpG ODNs hbu1555, psb1555, and pob1555 to CpG ODN 1555 (homologous to 2) occurred under elevated temperature conditions, thereby validating the function of these diastereomeric oligonucleotides as prodrugs in vitro. Noteworthy is the significant increase in solubility of CpG ODN psb1555 and CpG pob1555 in water when compared to that of neutral CpG ODN fma1555 (homologous to 1).

  DOI：

  10.1021/jo062087y
• 作为产物：
  描述：

  4-Oxo-pentanoic acid 4-allyloxy-butyl ester 在 Pd(PPh3) 1,3-二甲基巴比妥酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以98%的产率得到4-hydroxybutyl levulinate
  参考文献：
  名称：

  基于钯(0)-催化烯丙基烷基化N,N'-二甲基巴比妥酸的烯丙基醚的简便和选择性裂解

  摘要：

  N,N'-二甲基巴比妥酸的经典钯 (0) 催化烯丙基烷基化可用于烯丙基烷基醚的轻松和选择性裂解，以优异的产率释放相应的醇。 该反应在中性条件下进行，无需任何添加剂活化烯丙基醚并耐受各种官能团，如酯、醚、酮、烷基和芳基氯、腈和硝基。

  DOI：

  10.1055/s-2003-39320

文献信息

• Facile and Selective Cleavageof Allyl Ethers Based on Palladium(0)-Catalyzed Allylic Alkylationof<i>N</i>,<i>N</i>′-DimethylbarbituricAcid
  作者：Hirokazu Tsukamoto、Yoshinori Kondo

  DOI：10.1055/s-2003-39320

  日期：——

  The classical palladium(0)-catalyzed allylic alkylation of N,N'-dimethylbarbituric acid can be applied to the facile and selective cleavage of allylic alkyl ethers to release the corresponding alcohols in excellent yield.This reaction proceeds under neutral conditions without any additive to activate the allyl ethers and tolerates various functional groups, such as ester, ether, ketone, alkyl and aryl

  N,N'-二甲基巴比妥酸的经典钯 (0) 催化烯丙基烷基化可用于烯丙基烷基醚的轻松和选择性裂解，以优异的产率释放相应的醇。 该反应在中性条件下进行，无需任何添加剂活化烯丙基醚并耐受各种官能团，如酯、醚、酮、烷基和芳基氯、腈和硝基。
• KETOCARBOXYLIC ACIDS, METHODS OF MANUFACTURE AND USES THEREOF
  申请人：MULLEN Brian D.

  公开号：US20120123147A1

  公开（公告）日：2012-05-17

  Ketocarboxylic acids such as levulinic acid can be efficiently purified in high yield by esterification with a hydrocarbon polyol to the corresponding polyketocarboxylic ester, which can be readily purified, for example recrystallized. After purification, the ketocarboxylic ester can be hydrolyzed to provide pure ketocarboxylic acid, or a salt thereof, after removal of the esterifying hydrocarbon polyol, or used for other synthetic transformations. Advantageously, the polyketocarboxylic esters, ketocarboxylic acids, and salts thereof produced by this method are obtained in high purity.

  酮羧酸（如丙酮酸）可以通过与碳氢化合物多元醇酯化来高产率高效纯化，得到相应的多羟基酮羧酸酯，该酯可容易地纯化，例如再结晶。纯化后，酮羧酸酯可以水解以提供纯净的酮羧酸或其盐，在去除酯化碳氢化合物多元醇后，或用于其他合成转化。优点是，通过这种方法生产的多羟基酮羧酸酯、酮羧酸和盐具有高纯度。
• An Efficient Reagent for the Phosphorylation of Deoxyribonucleosides, DNA Oligonucleotides, and Their Thermolytic Analogues
  作者：Cristina Ausín、Andrzej Grajkowski、Jacek Cieślak、Serge L. Beaucage

  DOI：10.1021/ol0516263

  日期：2005.9.1

  and demonstrated efficiency in the synthesis of conventional 5'-/3'-phosphate/thiophosphate monoester derivatives of 2'-deoxyribonucleosides and DNA oligonucleotides. Moreover, the use of 11 has enabled the preparation of the dinucleoside phosphorothioate analogue 26 in high yields (>95%) with minimal cleavage (<2%) of the thermolytic thiophosphate protecting group.

  [反应：见正文]从2巯基乙酸甲酯分三步制备亚磷酰胺11，并证明了2'-脱氧核糖核苷的常规5'-/ 3'-磷酸酯/硫代磷酸酯单酯衍生物和DNA寡核苷酸的合成效率。而且，使用11使得能够以高收率（＞ 95％）制备二核苷硫代磷酸酯类似物26，而热解硫代磷酸酯保护基团的裂解最小（＜2％）。
• KETOCARBOXYLIC ACIDS, KETOCARBOXYLIC ESTERS, METHODS OF MANUFACTURE AND USES THEREOF
  申请人：SEGETIS, Inc.

  公开号：US20130296601A1

  公开（公告）日：2013-11-07

  Ketocarboxylic acids such as levulinic acid can be efficiently purified in high yield by esterification with a hydrocarbon polyol to the corresponding polyketocarboxylic ester, which can be readily purified, for example recrystallized. After purification, the ketocarboxylic ester can be hydrolyzed to provide pure ketocarboxylic acid, or a salt thereof, after removal of the esterifying hydrocarbon polyol, or used for other synthetic transformations. Advantageously, the polyketocarboxylic esters, ketocarboxylic acids, and salts thereof produced by this method are obtained in high purity.

  酮羧酸，例如丙酮酸，可以通过与烃基聚醇酯化反应形成相应的多酮羧酸酯，高效地、高产地进行纯化，例如再结晶。在纯化后，酮羧酸酯可以水解成纯酮羧酸或其盐，去除酯化的烃基聚醇后，或用于其他合成转化。优点是，通过该方法制备的多酮羧酸酯、酮羧酸及其盐具有高纯度。
• 10.1016/j.ica.2024.122299
  作者：Melchiorre, Massimo、Langellotti, Vincenzo、Campanile, Giuseppe、Elena Cucciolito, Maria、Esposito, Roberto、Tarallo, Oreste、Tuzi, Angela、Ruffo, Francesco

  DOI：10.1016/j.ica.2024.122299

  日期：——

  The valorization of renewable feedstocks to produce biochemicals and biofuels is an essential focus of contemporary research, with non-food crop biomass emerging as a cost-effective and environmentally friendly option. Among the chemicals derived from lignocellulosic biomass, levulinic acid (LAH) is a notable chemical platform due to its versatile applications. This study investigates the eco-friendly

  利用可再生原料生产生物化学品和生物燃料的价值是当代研究的一个重要焦点，非粮食作物生物质正在成为一种具有成本效益和环境友好的选择。在源自木质纤维素生物质的化学品中，乙酰丙酸 (LAH) 因其用途广泛而成为著名的化学平台。本研究研究了在温和、无溶剂的条件下，由锌 (II) 物质催化乙酰丙酸与多元醇的环保酯化反应。