(±)-cis-5-(2-hydroxyethyl)cyclopent-2-enol | 133969-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (±)-cis-5-(2-hydroxyethyl)cyclopent-2-enol
• 英文别名: (+/-)-cis-5-(2-hydroxyethyl)-2-cyclopenten-1-ol；(+/-)-cis-5-(2-hydroxyethyl)cyclopent-2-en-1-ol；cis-5-(2'-hydroxyethyl)-2-cyclopenten-1-ol；cis-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol；cis-5-(2-hydroxyethyl)-2-cyclopenten-1-ol；(1R,5S)-5-(2-hydroxyethyl)cyclopent-2-en-1-ol
• CAS: 133969-91-2
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: JFKRLRMLBGHFHE-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (±)-cis-5-(2-hydroxyethyl)cyclopent-2-enol 在 Wilkinson's catalyst 、 氢气 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 以60%的产率得到(+/-)-cis-2-(2-hydroxyethyl)cyclopentanol
  参考文献：
  名称：

  5-（2'-羟乙基）环戊-2-烯-1-醇和6-（2'-羟乙基）环己-2-烯-1-醇的区域选择性甲硅烷基化

  摘要：

  在这里，我们报告5-（2'-羟乙基）环戊-2-en-1-ol（2）和6-（2'-羟乙基）cyhehex-2-en对叔丁基二甲基甲硅烷基单保护的区域选择性反应和温和反应在伯羟基或仲烯丙基羟基上的-1-醇（5）。围绕仲烯丙基和饱和伯醇的不同空间环境主要是为了使观察到的区域选择性合理化。

  DOI：

  10.1016/j.tetlet.2012.02.020
• 作为产物：
  描述：

  (+)-cis-5-(2-acetyloxy-ethyl)cyclopent-2-en-1-ol 在 甲醇 、 sodium hydroxide 作用下， 以88%的产率得到(±)-cis-5-(2-hydroxyethyl)cyclopent-2-enol
  参考文献：
  名称：

  对映纯脂环族醚的合成及其对蜜蜂Varroa破坏物的寄生虫的化学感觉器官的活性

  摘要：

  本文报道了对映体构象受限的脂环族醚的制备及其对蜜蜂寄生虫Varroa的化学感觉器官的抑制活性。我们通过电生理学测试了顺式-5-（2'-羟乙基）环戊-2-烯-1-醇对映体纯醚对Varroa化学感官器官的抑制作用，因为它们能够抑制对两种蜜蜂产生的气味的反应螨对寄主的定位很重要：养蜂头部空间的气味和（E）-β-ocimene，蜂巢信息素。先前使用外消旋化合物的研究表明，它们能抑制螨对蜜蜂寄主的嗅觉反应，从而导致错误的寄主选择。根据结构与活性的关系，我们预测了两种活性最高的化合物-顺-1-丁氧基-5-（2'-甲氧基乙基）环戊-2-烯，cy {4,1}和（顺-1-乙氧基-5-（2'乙氧基乙基）环戊-2-烯，cy {2,2}-可能具有相反的活性对映体，在这里我们研究了两种醚的对映体，它们的制备涉及外消旋二醇顺式的酶促拆分使用脂肪酶AK和乙酸乙烯酯制备-5-（2'-羟乙基）环戊-2-烯-1-醇。外消旋二

  DOI：

  10.1021/acs.jafc.6b03492

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。
• Palladium-catalyzed synthesis of cis-2-[4-(9H-Purin-9-yl)-2-cyclopenten-1-yl]ethanol analogues
  作者：Lakshmi B. Akella、Robert Vince

  DOI：10.1016/0040-4020(96)00015-4

  日期：1996.2

  A concise 6–7 step synthesis of the carbocyclic nucleosides cis-2-[4-(9H-Purin-9-yl)-2-cyclopenten-1-yl]ethanol analogues utilizing palladium chemistry has been described.

  已经描述了利用钯化学的碳环核苷顺式-2- [4-（9 H-嘌呤-9-基）-2-环戊烯-1-基]乙醇类似物的6-7步骤简明合成方法。
• 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。
• A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters
  作者：Hao Chen、Srinivas Nagabandi、Steven Smith、Jonathan M. Goodman、Erika Plettner

  DOI：10.1016/j.tetasy.2009.02.007

  日期：2009.3

  The (+/-)-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol 1 was prepared in a one-pot procedure, and was resolved using lipase AK and vinyl acetate with high ee. This provides a readily available chiral synthon for the synthesis of a wide variety of biologically interesting molecules. Further, the absolute configuration of diol 1 was confirmed directly by the Mosher ester method. (c) 2009 Elsevier Ltd. All rights reserved.
• Use of radical ring opening for introduction of alkyl and substituted alkyl groups with stereochemical control: a synthetic application of cyclopropylcarbinyl radicals
  作者：Derrick L. J. Clive、Sylvain Daigneault

  DOI：10.1021/jo00012a009

  日期：1991.6

  Cyclopropylcarbinols 2a and 2b (see Scheme I), which are accessible by a number of routes, can be converted into the corresponding radicals 3a and 3b, respectively. These radicals undergo peripheral ring-opening of the cyclopropyl substructure to afford substituted cycloalkenes 4a and 4b. The whole sequence represents a general method for attaching alkyl, and substituted alkyl, groups to an existing cyclic structure, and it can often be carried out with predictable stereo- and regiochemical control. Reaction conditions for the ring-opening depend on the substitution pattern of the cyclopropane: where the non-bridgehead carbon of the cyclopropane carries a strongly electron-withdrawing group, the ring-opening can be done at the reflux temperature of benzene. However, in the absence of such electron-withdrawing groups, a low temperature is best used in order to suppress ring expansion. Various methods that accommodate these requirements are available for generating the radicals.