1-butyloxy-(-)-cis-5-(2-butyloxyethyl)cyclopent-2-ene | 1228640-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-butyloxy-(-)-cis-5-(2-butyloxyethyl)cyclopent-2-ene
• CAS: 1228640-78-5
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: IXGLRFJSMBPNCR-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  17.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  正溴丁烷 、 (1SR,5R)-(+)-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到1-butyloxy-(-)-cis-5-(2-butyloxyethyl)cyclopent-2-ene
  参考文献：
  名称：

  Synthesis and biological activity of conformationally restricted gypsy moth pheromone mimics

  摘要：

  The design and synthesis of a series of conformationally constrained mimics of gypsy moth sex pheromone, (+)-disparlure (7R,8S)-2-methyl-7,8-epoxyoctadecane, are described. The core structure of the mimics is derived from 5-(2'-hydroxyethyl) cyclopent-2-en-1-ol. Substituent optimization of the analogs was accomplished through the synthesis of mini-libraries and pure individual compounds, followed by electrophysiological experiments with male gypsy moth antennae. The electroantennogram results show that the analogs elicited weak to no antennal responses themselves. There was a clear structure-activity pattern for odorant activity, with ethyl substituents being best. Further, when puffed simultaneously with the pheromone, some of the compounds gave a significant enhancement of the antennal depolarization, indicating an additive or synergistic effect. A pure pheromone stimulus following a mixed compound/pheromone stimulus was generally not affected, with two exceptions: one compound enhanced and another inhibited a subsequent stimulus. The compounds also prolonged the stimulation of the antenna, which manifested itself in widened electroantennogram peaks. We tested the hypothesis that this prolonged stimulation may be due to the stabilization of a particular conformer of the pheromone-binding protein (PBP). Compounds that caused PBP2 to adopt a similar conformation than in the presence of pheromone also caused peak widening. This was not the case with PBP1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.061