庚烷-2-基丁酸酯 | 39026-94-3

• 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: 庚烷-2-基丁酸酯
• 英文名称: 1-methylhexyl butanoate
• 英文别名: heptan-2-yl butanoate；2-heptyl butanoate；butyric acid-(1-methyl-hexyl ester)；Buttersaeure-(1-methyl-hexylester)；butanoic acid 1-methylhexyl ester；n-Buttersaeureheptanol-(2)-ester；2-Heptyl butyrate
• CAS: 39026-94-3
• 化学式: C₁₁H₂₂O₂
• mdl: MFCD06796189
• 分子量: 186.294
• InChiKey: GTKUPJHQSAPWLL-UHFFFAOYSA-N

物化性质

• 熔点：
  -57.5°C (estimate)
• 沸点：
  220.8°C (estimate)
• 密度：
  0.8726 (estimate)
• LogP：
  4.24
• 物理描述：
  Colourless liquid
• 溶解度：
  insoluble in water; soluble in fats
• 折光率：
  1.413-1.417
• 保留指数：
  1230;1194;1199;1194;1198;1194;1197

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.909
• 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：

  庚烷-2-基丁酸酯 在 Candida antarctica lipase B immobilized on acrylic resin catalyst 作用下， 反应 8.0h， 生成 (R)-(-)-2-庚醇 、 (S)-2-heptyl butanoate 、 (R)-2-heptyl butanoate
  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 在 水 、 disodium;carbonate 、 丁酸酐 、 Sodium sulfate-III 、 crude residue 作用下， 以 丁酸酐 为溶剂， 85.0~160.0 ℃ 、1.42 MPa 条件下， 反应 5.5h， 以provided 1-methylhexyl butyrate (85-110°/78-80 mm Hg, 85% yield)的产率得到庚烷-2-基丁酸酯
  参考文献：
  名称：

  Methods for using 1-methylbutyl and 1-methylhexyl esters as flavoring

  摘要：

  本发明涉及一种由公式表示的纯化调味剂：CH.sub.3 (CH.sub.2).sub.n CH(CH.sub.3)OCOR，其中n为2或4，R为具有1至5个碳原子的低级烷基基团。该调味剂可用于各种可食用载体，如嚼胶组合物、硬质和软质糖果、乳制品、果汁产品等。本发明还涉及制备和使用该调味剂及其可食用产品的方法。

  公开号：

  US05993879A1

文献信息

• 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.
• Enantioselective transesterification catalysis by nanosized serine protease subtilisin Carlsberg particles in tetrahydrofuran
  作者：Betzaida Castillo、Yamixa Delgado、Gabriel Barletta、Kai Griebenow

  DOI：10.1016/j.tet.2010.01.053

  日期：2010.3

  Enzyme catalysis in organic solvents is a powerful tool for stereo-selective synthesis but the enantioselectivity is still hard to pi edict To overcome this obstacle. we employed a nanoparticulate formulation of subtilisin Carlsberg (SC) and designed a series of 14 structurally related racemic alcohols They were employed in the model transesterification reaction with vinyl butyrate and the enantioselectivities were determined. In general. short alcohol side chains led to low enantioselectivties, while larger and bulky side chains caused better discrimination of the enantiomers by the enzyme With several bulky substrates high enantioselectivities with E>100 were obtained Computational modeling highlighted that key to high enantioselectivity is the discrimination of the R and S substrates by the sole hydrophobic binding pocket based on their size and bulkiness While bulky S enantiomer side chains could be accommodated within the binding pocket, bulky R enantiomer side chains could not However, when also the S enantiomer side chain becomes too large and does not fit into the binding pocket anymore. enantioselectivity accordingly drops (C) 2010 Elsevier Ltd All rights reserved
• Iron Perchlorate on Silica Gel as Multi-purpose Reagent for Catalysis of Closure and Rupture of Carbon-Oxygen Bond in Epoxides, Alcohols, and Esters
  作者：P. Salechi、M. M. Khodaei、S. B. Ghareghani、A. R. Motlagh

  DOI：10.1023/b:rujo.0000003154.92028.84

  日期：2003.6

  Aliphatic alcohols and water in the presence of catalytic amounts of Fe3+ ion introduced as iron(Ill) perchlorate on silica gel carrier perform efficient regiospecific opening of an epoxy ring. Carbon acids esterification with various type alcohols was carried out using the system Fe(ClO4)(3)-silica gel in dichloromethane under conditions excluding solvolysis. Acetylation and formylation of alcohols was performed by efficient transesterification with ethyl acetate and ethyl formate.
• Hogan, V F; O'Hagan, D; Sanvoisin, J, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 883 - 885
  作者：Hogan, V F、O'Hagan, D、Sanvoisin, J

  DOI：——

  日期：——
• US5993879A
  申请人：——

  公开号：US5993879A

  公开（公告）日：1999-11-30

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