1-甲基己基辛酸酯 | 55193-32-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-甲基己基辛酸酯
• 英文名称: Caprylsaeure-2-heptanester
• 英文别名: Heptanol-2-caprylat；2-heptyl octanoate；octanoic acid-(1-methyl-hexyl ester)；Octansaeure-(1-methyl-hexylester)；1-methylhexyl octanoate；heptan-2-yl octanoate
• CAS: 55193-32-3
• 化学式: C₁₅H₃₀O₂
• 分子量: 242.402
• InChiKey: UKPOONOGHLYURR-UHFFFAOYSA-N

物化性质

• 保留指数：
  1788;1772

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基己基辛酸酯 在 Candida antarctica lipase B immobilized on acrylic resin catalyst 作用下， 反应 8.0h， 生成 (R)-(-)-2-庚醇 、 (R)-2-heptyl octanoate 、 (S)-2-heptyl octanoate
  参考文献：
  名称：

  脂肪酶催化动力学拆分制备百香果型典型的2-烷基酯对映体

  摘要：

  研究了通过脂肪酶催化动力学拆分制备仲醇2-戊醇，2-庚醇和2-壬醇的酯对映体（乙酸，丁酸酯，己酸酯和辛酸酯）。通过庚烷（2,3-di- O -methyl-6）的毛细管气相色谱法，对这些百香果类典型的2-烷基酯的同源系列进行了追踪，考察了市售酶制剂催化的酯化和水解反应的转化率和立体化学过程。- ø -叔丁基二）-β环糊精作为手性固定相。开发了一种通过脂肪酶催化的酯化反应制备酯对映体的有效方法：光学纯（R通过用对映选择性南极假丝酵母脂肪酶B（固定化）作为催化剂将外消旋醇酯化，可得到）-2-烷基酯（ee> 99.9％）。随后使用来自假丝酵母的脂肪酶将未反应的醇酯化，得到光学富集的（S）-酯（ee＞ 81.4％）。通过使用硅胶和氧化铝（碱性）的混合物的液体固体色谱法分离产物，得到高化学纯度和产率（＞ 40mol％）。

  DOI：

  10.1021/jf100432s
• 作为产物：
  描述：

  2-庚醇 、 辛酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 1-甲基己基辛酸酯
  参考文献：
  名称：

  Enantioselective Analysis of Secondary Alcohols and Their Esters in Purple and Yellow Passion Fruits

  摘要：

  The enantiomeric compositions of the acetates, butanoates, hexanoates, and octanoates of the secondary alcohols 2-pentanol, 2-heptanol, and 2-nonanol were determined in yellow (Passiflora edulis f. flavicarpa) and purple (Passiflora edulis Sims) passion fruits. The compounds were isolated by means of simultaneous distillation-extraction. Enantiodifferentiation was performed via multidimensional gas chromatography using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-beta-cyclodextrin as chiral stationary phase. The series of homologous 2-alkyl esters, which are typical constituents of purple passion fruits, were shown to be present as nearly optically pure (R)-enantiomers. The proportions of the (S)-enantiomers varied in different batches and were dependent on the alcohol moieties of the esters. For minor amounts of esters detected in yellow fruits, the (R)-enantiomers were also dominating. However, the enantiomeric excesses were significantly lower than in the purple variety. Enantioselective analysis of the free alcohols revealed that 2-heptanol exhibited opposite configurations in purple and yellow passion fruits. A similar phenomenon was observed for 2-pentanol, which was present in the yellow fruits as a nearly racemic mixture. Data determined in extracts obtained by other techniques (liquid-liquid extraction, vacuum headspace technique) showed that the isolation procedure had no significant impact on the enantiomeric ratios.

  DOI：

  10.1021/jf072464n

文献信息

• One-pot esters synthesis from secondary alcohols and CO catalyzed byPd-phosphine systems
  作者：Nadezhda T. Sevostyanova、Sergey A. Batashev、Anastasiya S. Rodionova、Dar'ya K. Kozlenko

  DOI：10.1016/j.tet.2023.133653

  日期：2023.10

  The aim of the work is to develop the esters syntheses by combining in one reactor the acid–catalytic intramolecular alcohols dehydration and the resulting alkenes alkoxycarbonylation. Esters were synthesized from cycloalkanols or secondary alkanols C5–C9 and CO under mild conditions. For the first time, a wide range of catalytic systems including palladium precursor, organophosphine, strong protonic

  这项工作的目的是通过在一个反应​​器中结合酸催化分子内醇脱水和由此产生的烯烃烷氧基羰基化来开发酯合成。在温和条件下，由环烷醇或仲烷醇C 5 –C 9与CO合成酯。首次在基于环己醇和 CO 的模型一锅法工艺中测试了多种催化体系，包括钯前体、有机膦、强质子酸和结合水添加剂。直链仲醇 C 6、C 7和 C 9与 XANTPHOS 促进剂一起在 Pd 系统催化的异构化烷氧基羰基化反应器中组合。这些过程导致异构酯的形成，其中 60-73% 是直链羧酸酯，是末端 CO 加成到烯烃上的产物。
• Schlenk,W., Justus Liebigs Annalen der Chemie, 1973, p. 1179 - 1194
  作者：Schlenk,W.

  DOI：——

  日期：——
• Enantioselective Analysis of Secondary Alcohols and Their Esters in Purple and Yellow Passion Fruits
  作者：Hedwig Strohalm、Márta Dregus、Astrid Wahl、Karl-Heinz Engel

  DOI：10.1021/jf072464n

  日期：2007.12.1

  The enantiomeric compositions of the acetates, butanoates, hexanoates, and octanoates of the secondary alcohols 2-pentanol, 2-heptanol, and 2-nonanol were determined in yellow (Passiflora edulis f. flavicarpa) and purple (Passiflora edulis Sims) passion fruits. The compounds were isolated by means of simultaneous distillation-extraction. Enantiodifferentiation was performed via multidimensional gas chromatography using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-beta-cyclodextrin as chiral stationary phase. The series of homologous 2-alkyl esters, which are typical constituents of purple passion fruits, were shown to be present as nearly optically pure (R)-enantiomers. The proportions of the (S)-enantiomers varied in different batches and were dependent on the alcohol moieties of the esters. For minor amounts of esters detected in yellow fruits, the (R)-enantiomers were also dominating. However, the enantiomeric excesses were significantly lower than in the purple variety. Enantioselective analysis of the free alcohols revealed that 2-heptanol exhibited opposite configurations in purple and yellow passion fruits. A similar phenomenon was observed for 2-pentanol, which was present in the yellow fruits as a nearly racemic mixture. Data determined in extracts obtained by other techniques (liquid-liquid extraction, vacuum headspace technique) showed that the isolation procedure had no significant impact on the enantiomeric ratios.
• Preparation of Passion Fruit-Typical 2-Alkyl Ester Enantiomers via Lipase-Catalyzed Kinetic Resolution
  作者：Hedwig Strohalm、Susanne Dold、Kathrin Pendzialek、Monika Weiher、Karl-Heinz Engel

  DOI：10.1021/jf100432s

  日期：2010.5.26

  fruit-typical 2-alkyl esters by capillary gas chromatography using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin as chiral stationary phase. An efficient method was developed to prepare the ester enantiomers via lipase-catalyzed esterifications: optically pure (R)-2-alkyl esters (ee > 99.9%) were obtained by esterification of the racemic alcohols with enantioselective Candida antarctica

  研究了通过脂肪酶催化动力学拆分制备仲醇2-戊醇，2-庚醇和2-壬醇的酯对映体（乙酸，丁酸酯，己酸酯和辛酸酯）。通过庚烷（2,3-di- O -methyl-6）的毛细管气相色谱法，对这些百香果类典型的2-烷基酯的同源系列进行了追踪，考察了市售酶制剂催化的酯化和水解反应的转化率和立体化学过程。- ø -叔丁基二）-β环糊精作为手性固定相。开发了一种通过脂肪酶催化的酯化反应制备酯对映体的有效方法：光学纯（R通过用对映选择性南极假丝酵母脂肪酶B（固定化）作为催化剂将外消旋醇酯化，可得到）-2-烷基酯（ee> 99.9％）。随后使用来自假丝酵母的脂肪酶将未反应的醇酯化，得到光学富集的（S）-酯（ee＞ 81.4％）。通过使用硅胶和氧化铝（碱性）的混合物的液体固体色谱法分离产物，得到高化学纯度和产率（＞ 40mol％）。