(1S)-1-Methylbutyl dodecanoate | 160296-83-3

• 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: (1S)-1-Methylbutyl dodecanoate
• 英文别名: (s)-1-Methylbutyl dodecanoate；[(2S)-pentan-2-yl] dodecanoate
• CAS: 160296-83-3
• 化学式: C₁₇H₃₄O₂
• 分子量: 270.456
• InChiKey: MMMPIDDNNZYIOB-INIZCTEOSA-N

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：

  月桂酰氯 、 (S)-(+)-2-戊醇 在 吡啶 作用下， 生成 (1S)-1-Methylbutyl dodecanoate
  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

• Enzyme reactions in apolar solvents. The resolution of branched and unbranched 2-alkanols by porcine pancreatic lipase.
  作者：Brian Morgani、Allan C. Oehlschlager、Thomas M. Stokes

  DOI：10.1016/s0040-4020(01)96905-4

  日期：1991.1

  Straight-chain and branched 2-alkanols were subjected to enzyme catalyzed transesterification in organic solvent using porcine pancreatic lipase, high enantioselectivity being generally observed. The method was applied to the synthesis of (R)-(-)-9-hydroxy-(E)-decenoic acid, a component of the queen bee mandibular gland pheromone.
• 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.