3-hydroxypropyl levulinate | 928625-01-8

• 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: 3-hydroxypropyl levulinate
• 英文别名: 3-Hydroxypropyl 4-oxopentanoate
• CAS: 928625-01-8
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: ZQCJLAQNDYNKRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  255.1±15.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  3-hydroxypropyl 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 5.0h， 生成 3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropyl 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：

  乙酰丙酸 、 1,3-丙二醇 在 D(+)-10-樟脑磺酸 作用下， 反应 4.67h， 生成 3-hydroxypropyl levulinate
  参考文献：
  名称：

  [EN] POLYHYDROXY KETAL ESTER ADDUCTS, METHODS OF MANUFACTURE AND USES THEREOF
  [FR] ADDUITS DE POLYHYDROXY CÉTAL ESTER, LEURS PROCÉDÉS DE FABRICATION ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2012065116A3

文献信息

• Acid Catalyzed Competitive Esterification and Ketalization of Levulinic Acid with 1,2 and 1,3-Diols: The Effect of Heterogeneous and Homogeneous Catalysts
  作者：Ananda S. Amarasekara、Moriam A. Animashaun

  DOI：10.1007/s10562-016-1812-8

  日期：2016.9

  reactions of levulinic acid (LA) with 1,2-ethanediol (1,2-ED), 1,2-propanediol (1,2-PD), and 1,3-propanediol (1,3-PD) were studied using Amberlyst-15 as well as p-toluenesulfonic acid catalysts in benzene under Dean–Stark conditions. In Amberlyst-15 catalyzed reactions the products are ketals and ketal-esters, whereas p-toluenesulfonic acid catalyzed reactions produce esters and ketal-esters as products

  研究了乙酰丙酸 (LA) 与 1,2-乙二醇 (1,2-ED)、1,2-丙二醇 (1,2-PD) 和 1,3-丙二醇 (1,3-PD) 的缩合反应在 Dean-Stark 条件下，在苯中使用 Amberlyst-15 和对甲苯磺酸催化剂。在 Amberlyst-15 催化反应中，产物是缩酮和缩酮酯，而对甲苯磺酸催化反应生成酯和缩酮酯作为产物。在对甲苯磺酸催化的 1,2-ED 和 1,3-PD 反应中，LA 单酯产物在 180 分钟后作为主要产物形成，产率分别为 75% 和 97%。与之前报道的乙酰丙酸乙酯与二醇的酸催化缩酮化不同，LA 与二醇的缩酮化-酯化反应是一个复杂的过程。
• POLYHYDROXY KETAL ESTER ADDUCTS, METHODS OF MANUFACTURE AND USES THEREOF
  申请人：Mullen Brian D.

  公开号：US20120121911A1

  公开（公告）日：2012-05-17

  Disclosed herein is a polyhydroxy ketal adduct obtained by the esterification of a hydrocarbon polyol by at least 1.5 equivalents of a ketocarboxy to produce an intermediate ketocarboxylic ester. The intermediate polyketocarboxylic ester is then ketalized to produce the polyhydroxyketal adduct, which can be used to provide a polymeric composition.
• SYNTHESIS OF DIESEL FUEL BLENDSTOCK FROM CARBOHYDRATES
  申请人：PHILLIPS 66 COMPANY

  公开号：US20140350292A1

  公开（公告）日：2014-11-27

  Carbohydrates as derived from plant biomass can be converted into mono-alcohols, diols, and/or bi-functional alcohols or into carboxylic acid derivatives. By catalytic transesterification of such carbohydrate derivatives, ester-type diesel-fuel blendstock components may be produced. More specifically, alkyl levulinates are catalytically trans-esterified with hydroxyl-functionalized compounds where both the alcohols and the alkyl levulinates are derived from biomass carbohydrates. Esters produced in this way show physicochemical characteristics that make them suitable for use as diesel fuel blendstock.
• US9181506B2
  申请人：——

  公开号：US9181506B2

  公开（公告）日：2015-11-10
• US9187598B2
  申请人：——

  公开号：US9187598B2

  公开（公告）日：2015-11-17