dimethyl CP

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl CP
• 英文别名: 1-methoxy-(+/-)-cis-5-(2-methoxyethyl)cyclopent-2-ene；(3R,4S)-3-methoxy-4-(2-methoxyethyl)cyclopentene
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: MXPAJNUKFMCGDG-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 potassium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 dimethyl CP
  参考文献：
  名称：

  Can We Disrupt the Sensing of Honey Bees by the Bee Parasite Varroa destructor?

  摘要：

  背景 外寄生性螨虫 Varroa destructor 被认为是全世界养蜂业面临的最大威胁之一。众所周知，化学线索在瓦氏螨寻找寄主的行为中起着重要作用。这种螨虫会区分不同任务群的蜜蜂，并且更喜欢哺育者而不是觅食者。我们研究了通过针对瓦氏螨的嗅觉系统来破坏瓦氏螨与蜜蜂相互作用的可能性。我们特别研究了挥发性化合物、顺式 5-（2′-羟乙基）环戊-2-烯-1-醇醚或二氢醌、间苯二酚或儿茶酚的影响。我们通过电生理学和选择生物测定法测试了这些化合物对 Varroa 化学感觉器官和行为的影响。电生理学研究是在离体的前肢上进行的。在行为生物测定中，对螨虫在哺育蜂和觅食蜂之间的偏好进行了评估。 主要研究结果 我们发现，在某些化合物存在的情况下，瓦氏螨化感器官对蜜蜂顶空挥发物的反应明显降低。这种效应与剂量有关，其中一些化合物的效应持续时间较长（>1 分钟）。此外，瓦氏螨挥发物检测中断的同时，瓦氏螨的偏好也从哺育蜂逆转为觅食蜂。螨虫对测试化合物的电生理反应的长期抑制是螨虫宿主偏好改变的良好预测。 结论 这些数据表明，所选化合物有可能破坏瓦氏螨与蜜蜂之间的联系，从而为瓦氏螨的控制开辟了新的途径。

  DOI：

  10.1371/journal.pone.0106889

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。
• 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.
• Can We Disrupt the Sensing of Honey Bees by the Bee Parasite Varroa destructor?
  作者：Nurit Eliash、Nitin Kumar Singh、Yosef Kamer、Govardhana Reddy Pinnelli、Erika Plettner、Victoria Soroker

  DOI：10.1371/journal.pone.0106889

  日期：——

  Background The ectoparasitic mite, Varroa destructor, is considered to be one of the most significant threats to apiculture around the world. Chemical cues are known to play a significant role in the host-finding behavior of Varroa. The mites distinguish between bees from different task groups, and prefer nurses over foragers. We examined the possibility of disrupting the Varroa – honey bee interaction by targeting the mite's olfactory system. In particular, we examined the effect of volatile compounds, ethers of cis 5-(2′-hydroxyethyl) cyclopent-2-en-1-ol or of dihydroquinone, resorcinol or catechol. We tested the effect of these compounds on the Varroa chemosensory organ by electrophysiology and on behavior in a choice bioassay. The electrophysiological studies were conducted on the isolated foreleg. In the behavioral bioassay, the mite's preference between a nurse and a forager bee was evaluated. Principal findings We found that in the presence of some compounds, the response of the Varroa chemosensory organ to honey bee headspace volatiles significantly decreased. This effect was dose dependent and, for some of the compounds, long lasting (>1 min). Furthermore, disruption of the Varroa volatile detection was accompanied by a reversal of the mite's preference from a nurse to a forager bee. Long-term inhibition of the electrophysiological responses of mites to the tested compounds was a good predictor for an alteration in the mite's host preference. Conclusions These data indicate the potential of the selected compounds to disrupt the Varroa - honey bee associations, thus opening new avenues for Varroa control.

  背景 外寄生性螨虫 Varroa destructor 被认为是全世界养蜂业面临的最大威胁之一。众所周知，化学线索在瓦氏螨寻找寄主的行为中起着重要作用。这种螨虫会区分不同任务群的蜜蜂，并且更喜欢哺育者而不是觅食者。我们研究了通过针对瓦氏螨的嗅觉系统来破坏瓦氏螨与蜜蜂相互作用的可能性。我们特别研究了挥发性化合物、顺式 5-（2′-羟乙基）环戊-2-烯-1-醇醚或二氢醌、间苯二酚或儿茶酚的影响。我们通过电生理学和选择生物测定法测试了这些化合物对 Varroa 化学感觉器官和行为的影响。电生理学研究是在离体的前肢上进行的。在行为生物测定中，对螨虫在哺育蜂和觅食蜂之间的偏好进行了评估。 主要研究结果 我们发现，在某些化合物存在的情况下，瓦氏螨化感器官对蜜蜂顶空挥发物的反应明显降低。这种效应与剂量有关，其中一些化合物的效应持续时间较长（>1 分钟）。此外，瓦氏螨挥发物检测中断的同时，瓦氏螨的偏好也从哺育蜂逆转为觅食蜂。螨虫对测试化合物的电生理反应的长期抑制是螨虫宿主偏好改变的良好预测。 结论 这些数据表明，所选化合物有可能破坏瓦氏螨与蜜蜂之间的联系，从而为瓦氏螨的控制开辟了新的途径。