(1SR,5R)-(+)-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol | 200484-81-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1SR,5R)-(+)-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol
• 英文别名: (1S,5R)-(-)-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol；(1S,5R)-5-(2-hydroxyethyl)cyclopent-2-en-1-ol
• CAS: 200484-81-7
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: JFKRLRMLBGHFHE-RNFRBKRXSA-N

物化性质

• 沸点：
  245.3±23.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

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：

  (1SR,5R)-(+)-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (-)-2-((1R,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-enyl)ethanol
  参考文献：
  名称：

  Enantioselective syntheses of 5′-homo-carbocyclic nucleosides

  摘要：

  Efficient enantioselective syntheses of 5'-homo-carbocyclic nucleosides (3 and 4) starting from (-)-4-endo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one (5) are presented. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00518-1
• 作为产物：
  描述：

  (-)-cis-5-(2-acetyloxy-ethyl)-1-acetyloxy-cyclopent-2-ene 在 甲醇 、 sodium hydroxide 作用下， 生成 (1SR,5R)-(+)-5-(2'-hydroxyethyl)cyclopent-2-en-1-ol
  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

• 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.
• 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.
• Synthesis of Enantiopure Alicyclic Ethers and Their Activity on the Chemosensory Organ of the Ectoparasite of Honey Bees, <i>Varroa destructor</i>
  作者：Govardhana R. Pinnelli、Nitin K. Singh、Victoria Soroker、Erika Plettner

  DOI：10.1021/acs.jafc.6b03492

  日期：2016.11.16

  opent-2-ene, cy2,2}—could have opposite active enantiomers. Here we studied the enantiomers of both ethers, whose preparation involved enzymatic resolution of racemic diol cis-5-(2′-hydroxyethyl)cyclopent-2-en-1-ol using Lipase AK with vinyl acetate. The racemic diol was prepared from commercially available 2,5-norbornadiene. We observed that the responses of the chemosensory organ to honey bee head

  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
• Enantioselective syntheses of 5′-homo-carbocyclic nucleosides
  作者：Horacio F. Olivo、Jiaxin Yu

  DOI：10.1016/s0957-4166(97)00518-1

  日期：1997.11

  Efficient enantioselective syntheses of 5'-homo-carbocyclic nucleosides (3 and 4) starting from (-)-4-endo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one (5) are presented. (C) 1997 Elsevier Science Ltd.