5-(2′-propoxyethyl)-1-propoxycyclopent-2-ene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2′-propoxyethyl)-1-propoxycyclopent-2-ene
• 英文别名: dipropyl CP；1-propyloxy-(+/-)-cis-5-(2-propyloxyethyl)cyclopent-2-ene；(3R,4S)-3-propoxy-4-(2-propoxyethyl)cyclopentene
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: UUOBBYAFNLUVOP-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (±)-cis-5-(2-hydroxyethyl)cyclopent-2-enol 、 溴丙烷 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到5-(2′-propoxyethyl)-1-propoxycyclopent-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

文献信息

• Screening of Dialkoxybenzenes and Disubstituted Cyclopentene Derivatives against the Cabbage Looper, Trichoplusia ni, for the Discovery of New Feeding and Oviposition Deterrents
  作者：Yasmin Akhtar、Murray B. Isman、Peggy M. Paduraru、Srinivas Nagabandi、Ranjeet Nair、Erika Plettner

  DOI：10.1021/jf071636d

  日期：2007.12.1

  with some exhibiting strong toxic and oviposition deterrent effects as well. Our results suggest some structure-function relationships within these libraries. Replacement of a methyl group with larger alkyl substituents increased the feeding deterrent effects in most cases. The presence of a free hydroxyl group, irrespective of the carbon framework or alkyl substituent, served to reduce feeding deterrent

  评估了二烷氧基苯微型文库和二取代的环戊烯微型文库（即由4至5种化合物组成）及其纯组分的拒食性，产卵威慑力和毒性作用，针对三龄幼虫和卷心菜弯尾毛癣菌Trichoplusia ni的成虫进行了研究。寻找新的昆虫防治剂的实验室生物测定。这些化合物模仿天然存在的生物活性气味和味道，并且相对容易从商品化学品中制备。这些文库中的大多数都强烈阻止了幼虫的进食，有些还表现出强烈的毒性和产卵阻吓作用。我们的结果表明这些库中存在一些结构-功能关系。在大多数情况下，用较大的烷基取代基取代甲基可增强进料的威慑作用。游离羟基的存在，无论碳骨架或烷基取代基如何，都可降低所有系列化合物的进料威慑作用。此外，超过特定的组规模通常也具有有害作用。这些信息将有助于设计新型的农业防虫剂。这些文库和化合物中的某些可能具有作为商业杀虫剂开发的潜力。
• METHODS AND COMPOSITIONS FOR CONTROL OF GYPSY MOTH, Lymantria dispar
  申请人：PLETTNER ERIKA

  公开号：US20130045178A1

  公开（公告）日：2013-02-21

  The invention provides in part dialkoxybenzene and eugenol compounds for controlling infestation by a Lymantria dispar , and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; with the provisos that when R2 is at position 2, R3 if present is at position 3, or when R2 is at position 3, R3 if present is at positions 2 or 4, or when R2 is at position 4, R3 if present is at position 2; or of Formula II: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; or mixtures thereof.
• Synthesis and biological activity of conformationally restricted gypsy moth pheromone mimics
  作者：Hao Chen、Yongmei Gong、Regine M. Gries、Erika Plettner

  DOI：10.1016/j.bmc.2010.02.061

  日期：2010.4

  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.