十八烷基呋喃-2-羧酸酯 | 82701-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 十八烷基呋喃-2-羧酸酯
• 英文名称: octadecyl furan-2-carboxylate
• CAS: 82701-01-7
• 化学式: C₂₃H₄₀O₃
• 分子量: 364.569
• InChiKey: OEQDALBGMFPWRY-UHFFFAOYSA-N

物化性质

• 熔点：
  47-48 °C
• 沸点：
  451.4±18.0 °C(Predicted)
• 密度：
  0.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-糠酸甲酯 、 硬脂醇 在 titanium(IV) oxide bis(2,4-pentanedionate) 作用下， 以 xylene 为溶剂， 反应 13.5h， 以93%的产率得到十八烷基呋喃-2-羧酸酯
  参考文献：
  名称：

  Nucleophilic Acyl Substitutions of Esters with Protic Nucleophiles Mediated by Amphoteric, Oxotitanium, and Vanadyl Species

  摘要：

  [GRAPHICS]A diverse array of oxometallic species were examined as catalysts in nucleophilic acyl substitution (NAS) reactions of methyl (or ethyl) esters with protic nucleophiles. Among them, oxotitanium acetylacetonate (TiO(acac)(2)) and vanadyl chloride (VOCl2-(THF)(x)) served as the most efficient and water-tolerant catalysts. Transesterifications of methyl and/or ethyl esters with functionalized (including acid- or base-sensitive) 1degrees and 2degrees alcohols can be carried out chemoselectively in refluxed toluene or xylene in a 1:1 substrate stoichiometry using 1 mol % catalyst loading. The resultant products were furnished in 85-100% yields by simple aqueous workup to remove water-soluble catalysts. The new NAS protocol is also amenable to amines and thiols in 74-91% yields, albeit with higher loading (2.5 equiv) of protic nucleophiles. Representative examples of commercial interests such as Padimate 0 and antioxidant additives for plastics were also examined to demonstrate their practical applications. A 1:1 adduct between TiO(acac)2 and a given 1-octadecanol was identified as (C18H37O)(2)Ti(acac)(2) and was responsible for its subsequent NAS of methyl esters.

  DOI：

  10.1021/jo0484878

文献信息

• Oxidative benzoin reactions
  作者：J. Castells、F. Pujol、H. Llitjós、M. Moreno-Mañas

  DOI：10.1016/0040-4020(82)80170-1

  日期：1982.1

  A one-pot synthesis (yields over 50%) of methyl and ethyl esters from aldehydes (and the corresponding alcohol), using aromatic nitrocompounds as oxidizing agents under the catalytic action of cyanide ion or of a conjugate base of a thiazolium ion, is described. A variety of by-products (α-hydroxybenzylidenaniline) (16), α-methoxybenzylidenaniline (21), α-cyanobenzylidenaniline (27), N1-hydroxy-N1

  描述了在氰化物离子或噻唑鎓离子的共轭碱的催化作用下，使用芳香族硝基化合物作为氧化剂，由醛（和相应的醇）一锅法合成（收率超过50％）甲基和乙基酯的方法。 。已经产生了多种副产物（α-羟基苄基苯胺（16），α-甲氧基苄基苯胺（21），α-氰基苄基苯胺（27），N 1-羟基-N 1，N 2-二苯基苯甲m （28）等）。确定。
• Nucleophilic Acyl Substitutions of Esters with Protic Nucleophiles Mediated by Amphoteric, Oxotitanium, and Vanadyl Species
  作者：Chien-Tien Chen、Jen-Huang Kuo、Cheng-Hsiu Ku、Shiue-Shien Weng、Cheng-Yuan Liu

  DOI：10.1021/jo0484878

  日期：2005.2.1

  [GRAPHICS]A diverse array of oxometallic species were examined as catalysts in nucleophilic acyl substitution (NAS) reactions of methyl (or ethyl) esters with protic nucleophiles. Among them, oxotitanium acetylacetonate (TiO(acac)(2)) and vanadyl chloride (VOCl2-(THF)(x)) served as the most efficient and water-tolerant catalysts. Transesterifications of methyl and/or ethyl esters with functionalized (including acid- or base-sensitive) 1degrees and 2degrees alcohols can be carried out chemoselectively in refluxed toluene or xylene in a 1:1 substrate stoichiometry using 1 mol % catalyst loading. The resultant products were furnished in 85-100% yields by simple aqueous workup to remove water-soluble catalysts. The new NAS protocol is also amenable to amines and thiols in 74-91% yields, albeit with higher loading (2.5 equiv) of protic nucleophiles. Representative examples of commercial interests such as Padimate 0 and antioxidant additives for plastics were also examined to demonstrate their practical applications. A 1:1 adduct between TiO(acac)2 and a given 1-octadecanol was identified as (C18H37O)(2)Ti(acac)(2) and was responsible for its subsequent NAS of methyl esters.