(R)-2-Pentyl decanoate

• 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: (R)-2-Pentyl decanoate
• 英文别名: (1R)-1-Methylbutyl decanoate；[(2R)-pentan-2-yl] decanoate
• 化学式: C₁₅H₃₀O₂
• 分子量: 242.402
• InChiKey: SUDINHDYWVJZKB-CQSZACIVSA-N

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：

  (R)-2-Pentyl decanoate 生成 (R)-2-pentanol
  参考文献：
  名称：

  NEAL, J. W. ,, JR.;KLUN, J. A.;SCHWARZ, M.;LEONHARDT, B. A.

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-2-pentanol 、 癸酰氯 在 吡啶 作用下， 生成 (R)-2-Pentyl decanoate
  参考文献：
  名称：

  Chiral esters: Sex pheromone of the bagworm,Oiketicus kirbyi (Lepidoptera: Psychidae)

  摘要：

  Gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract of female bagworms, Oiketicus kirbyi (Guilding), revealed five EAD-active compounds. Retention index calculations, GC-mass spectrometry in both full-scan and selected-ion monitoring modes and GC-EAD analyses of authentic standards identified the compounds as 1-methylbutyl octanoate (MBO), 1-methylbutyl nonanoate (MEN), 1-methylbutyl decanoate (MBD), 1-methylpentyl decanoate (MPD), and 1-methylbutyl dodecanoate (MBDD). Of these five chiral esters, MBD was most abundant in extracts and elicited the strongest antennal response. In field experiments in Costa Rica, (R)-MBD attracted O. kirbyi males, whereas (S)-MBD in combination with (R)-MBD inhibited response. R but not S enantiomers of MBO, MEN, and MBDD strongly synergized attraction to (R)-MBD. (S)-MBO and (S)-MBDD were inactive, whereas (S)-MBN was inhibitory. (R)-, (S)- and racemic MPD were inactive. Blends of (R)-MBD in ternary combination with either (R)-MBO and (R)-MBN or (R)-MBN and (R)-MBDD were as attractive as the five-ester blend. Five- and four-ester blends were equally attractive, suggesting redundancy of pheromone components for attraction of males. The multiple sex pheromone component blend of chiral esters in O. kirbyi may have evolved to maintain species-specific communication in bagworm communities of tropical Americas.

  DOI：

  10.1007/bf02033712

文献信息

• A green resolution–separation process for aliphatic secondary alcohols
  作者：Liwei Ren、Tian Xu、Ruoping He、Zhenhua Jiang、Hua Zhou、Ping Wei

  DOI：10.1016/j.tetasy.2013.01.018

  日期：2013.3

  In order to obtain both enantiomers of aliphatic secondary alcohols via a greener method, the four-step resolution-separation process involving lipase-catalyzed enantioselective esterification and hydrolysis as well as two separation procedures both via heterogeneous azeotropic distillation was developed. (S)-2-Pentanol (ee = 98.6%), (R)-2-pentanol (ee >99%), (S)-2-octanol (ee = 98.2%), and (R)-2-octanol (ee = 98.5%) were all produced in high purity (>98%) and high yield (>90%). In addition to the two model substrates, this method could also be applied to the resolution of other aliphatic secondary alcohols. (C) 2013 Elsevier Ltd. All rights reserved.
• NEAL, J. W. ,, JR.;KLUN, J. A.;SCHWARZ, M.;LEONHARDT, B. A.
  作者：NEAL, J. W. ,, JR.、KLUN, J. A.、SCHWARZ, M.、LEONHARDT, B. A.

  DOI：——

  日期：——
• Chiral esters: Sex pheromone of the bagworm,Oiketicus kirbyi (Lepidoptera: Psychidae)
  作者：Marc Rhainds、Gerhard Gries、Jianxiong Li、Regine Gries、Keith N. Slessor、Carlos M. Chinchilla、A. Cameron Oehlschlager

  DOI：10.1007/bf02033712

  日期：1994.12

  Gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract of female bagworms, Oiketicus kirbyi (Guilding), revealed five EAD-active compounds. Retention index calculations, GC-mass spectrometry in both full-scan and selected-ion monitoring modes and GC-EAD analyses of authentic standards identified the compounds as 1-methylbutyl octanoate (MBO), 1-methylbutyl nonanoate (MEN), 1-methylbutyl decanoate (MBD), 1-methylpentyl decanoate (MPD), and 1-methylbutyl dodecanoate (MBDD). Of these five chiral esters, MBD was most abundant in extracts and elicited the strongest antennal response. In field experiments in Costa Rica, (R)-MBD attracted O. kirbyi males, whereas (S)-MBD in combination with (R)-MBD inhibited response. R but not S enantiomers of MBO, MEN, and MBDD strongly synergized attraction to (R)-MBD. (S)-MBO and (S)-MBDD were inactive, whereas (S)-MBN was inhibitory. (R)-, (S)- and racemic MPD were inactive. Blends of (R)-MBD in ternary combination with either (R)-MBO and (R)-MBN or (R)-MBN and (R)-MBDD were as attractive as the five-ester blend. Five- and four-ester blends were equally attractive, suggesting redundancy of pheromone components for attraction of males. The multiple sex pheromone component blend of chiral esters in O. kirbyi may have evolved to maintain species-specific communication in bagworm communities of tropical Americas.