2-pentyl dodecanoate | 140390-73-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-pentyl dodecanoate
• 英文别名: lauric acid-(1-methyl-butyl ester)；Laurinsaeure-(1-methyl-butylester)；Laurinsaeure-2-pentylester；Pentan-2-YL dodecanoate；pentan-2-yl dodecanoate
• CAS: 140390-73-4；55195-18-1
• 化学式: C₁₇H₃₄O₂
• 分子量: 270.456
• InChiKey: MMMPIDDNNZYIOB-UHFFFAOYSA-N

物化性质

• 沸点：
  273-278 °C
• 密度：
  0.864±0.06 g/cm3(Predicted)
• 保留指数：
  1804

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  月桂酸 、 2-戊醇 在 硫酸 作用下， 以58.8%的产率得到2-pentyl dodecanoate
  参考文献：
  名称：

  Dodecanoic acid derivatives: Synthesis, antimicrobial evaluation and development of one-target and multi-target QSAR models

  摘要：

  In this study a series of dodecanoic acid derivatives (1-30) were synthesized and evaluated for in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. 4-Nitro phenyl dodecanoate (4) and quinolin-8-yl dodecanoate (5) emerged as most effective antibacterial agents, and 1-(4-benzylpiperazin-1-yl) dodecan-1-one (15) was found to be the most effective antifungal agent amongst the synthesized dodecanoic acid derivatives. Quantitative structure activity relationship (QSAR) studies performed by the development of one-target and multi-target models indicated that multi-target model was effective in describing the antimicrobial activity of dodecanoic acid derivatives as well demonstrated the importance of topological parameter, zero-order molecular connectivity index ((0)chi).

  DOI：

  10.1007/s00044-010-9383-5

文献信息

• Identification of Esters as Novel Aggregation Pheromone Components Produced by the Male Powder-Post Beetle, Lyctus africanus Lesne (Coleoptera: Lyctinae)
  作者：Titik Kartika、Nobuhiro Shimizu、Tsuyoshi Yoshimura

  DOI：10.1371/journal.pone.0141799

  日期：——

  Lyctus africanus is a cosmopolitan powder-post beetle that is considered one of the major pests threatening timber and timber products. Because infestations of this beetle are inconspicuous, damage is difficult to detect and identification is often delayed. We identified the chemical compounds involved in the aggregation behavior of L. africanus using preparations of crude hexanic extracts from male and female beetles (ME and FE, respectively). Both male and female beetles showed significant preferences for ME, which was found to contain three esters. FE was ignored by both the sexes. Further bioassay confirmed the role of esters in the aggregation behavior of L. africanus. Three esters were identified as 2-propyl dodecanoate, 3-pentyl dodecanoate, and 3-pentyl tetradecanoate. Further behavioral bioassays revealed 3-pentyl dodecanoate to play the main role in the aggregation behavior of female L. africanus beetles. However, significantly more beetles aggregated on a paper disk treated with a blend of the three esters than on a paper disk treated with a single ester. This is the first report on pheromone identification in L. africanus; in addition, the study for the first time presents 3-pentyl dodecanoate as an insect pheromone.

  非洲木屑甲虫（Lyctus africanus）是一种广泛分布的粉虫，被认为是威胁木材和木制品的主要害虫之一。由于这种甲虫的 infestation 不易察觉，损害难以发现，识别常常延迟。我们使用来自雄性和雌性甲虫的粗六烷提取物（分别称为 ME 和 FE）识别了与 L. africanus 聚集行为相关的化学化合物。雄性和雌性甲虫均显示出对 ME 的显著偏好，ME 中发现含有三种酯。FE 则被两性甲虫忽视。进一步的生物测定确认了酯在 L. africanus 聚集行为中的作用。三种酯被识别为 2-丙基月桂酸酯、3-戊基月桂酸酯和 3-戊基十四酸酯。进一步的行为生物测定显示，3-戊基月桂酸酯在雌性 L. africanus 甲虫的聚集行为中发挥了主要作用。然而，显著更多的甲虫聚集在涂有三种酯混合物的纸盘上，而不是涂有单一酯的纸盘上。这是首次关于 L. africanus 信息素鉴定的报告; 此外，本研究首次提出 3-戊基月桂酸酯作为一种昆虫信息素。
• Schlenk,W., Justus Liebigs Annalen der Chemie, 1973, p. 1179 - 1194
  作者：Schlenk,W.

  DOI：——

  日期：——
• Dodecanoic acid derivatives: Synthesis, antimicrobial evaluation and development of one-target and multi-target QSAR models
  作者：Devinder Sarova、Archana Kapoor、Rakesh Narang、Vikramjeet Judge、Balasubramanian Narasimhan

  DOI：10.1007/s00044-010-9383-5

  日期：2011.7

  In this study a series of dodecanoic acid derivatives (1-30) were synthesized and evaluated for in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. 4-Nitro phenyl dodecanoate (4) and quinolin-8-yl dodecanoate (5) emerged as most effective antibacterial agents, and 1-(4-benzylpiperazin-1-yl) dodecan-1-one (15) was found to be the most effective antifungal agent amongst the synthesized dodecanoic acid derivatives. Quantitative structure activity relationship (QSAR) studies performed by the development of one-target and multi-target models indicated that multi-target model was effective in describing the antimicrobial activity of dodecanoic acid derivatives as well demonstrated the importance of topological parameter, zero-order molecular connectivity index ((0)chi).