ethyl (RS)-2-(3-phenylcyclohexyliden)acetate | 198132-51-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (RS)-2-(3-phenylcyclohexyliden)acetate
• 英文别名: ethyl (3-phenylcyclohexylidene)acetate；ethyl 2-(3-phenylcyclohexylidene)acetate
• CAS: 198132-51-3
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: DDEUNAQVZNRIGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl (RS)-2-(3-phenylcyclohexyliden)acetate 在 甲烷 、 palladium dichloride 氢氧化钾 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 (3-苯基-环己基)-乙酸
  参考文献：
  名称：

  Kuchar, Miroslav; Brunova, Bohumila; Grimova, Jaroslava, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 12, p. 2896 - 2908

  摘要：

  DOI：
• 作为产物：
  描述：

  3-羟基-5-苯基-2-环己烯-1-酮 在 甲烷 、 palladium dichloride 氢气 、 sodium methylate 、 sodium hydride 作用下， 以 盐酸 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 ethyl (RS)-2-(3-phenylcyclohexyliden)acetate
  参考文献：
  名称：

  Kuchar, Miroslav; Brunova, Bohumila; Grimova, Jaroslava, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 12, p. 2896 - 2908

  摘要：

  DOI：

文献信息

• Tandem Michael−Wittig−Horner Reaction: One-Pot Synthesis of δ-Substituted α,β-Unsaturated Carboxylic Acid Derivatives − Application to a Concise Synthesis of (Z)- and (E)-Ochtoden-1-al
  作者：Olivier Piva、Sébastien Comesse

  DOI：10.1002/1099-0690(200007)2000:13<2417::aid-ejoc2417>3.0.co;2-x

  日期：2000.7

  A new tandem Michael−Wittig−Horner reaction has been developed to produce in high yields δ-substituted α,β-unsaturated esters, amides and lactones. The reaction has been successfully applied to a concise synthesis of (E)- and (Z)-ochtoden-1-als, components of the male sex pheromone of boll weevil from 3-methylcyclohex-2-en-1-one.

  已经开发出一种新的串联 Michael-Wittig-Horner 反应以高产率生产 δ-取代的 α,β-不饱和酯、酰胺和内酯。该反应已成功应用于从 3-methylcyclohex-2-en-1-one 合成棉铃象甲雄性信息素的 (E)- 和 (Z)-ochtoden-1-als 组分。
• Tandem Michaël-Wittig Horner reaction one-pot synthesis of δ-substituted α,β-unsaturated esters
  作者：Olivier Piva、Sébastien Comesse

  DOI：10.1016/s0040-4039(97)01729-2

  日期：1997.10

  direct synthesis of δ-substituted α,β-unsaturated esters from unsubstituted al dehydes or ketones has been accomplished in high yield by a taodem 1,4-addition and Wittig-Horner reaction. The Copper-enolate obtained after the first step was able to deprotonate the highly acidic phosphonate generating thus the two components necessary for the second coupling reaction.

  由未取代的醛或酮直接合成δ取代的α，β-不饱和酯的方法是通过1,4- taodem加成和Wittig-Horner反应以高收率完成。在第一步之后获得的烯醇铜能够使高酸性的膦酸酯去质子化，从而产生第二次偶联反应所必需的两种组分。
• Diastereoselective synthesis and structure–affinity relationships of <i>σ</i>₁ receptor ligands with spirocyclic scaffold
  作者：Tobias Winge、Dirk Schepmann、Judith Schmidt、Constantin Daniliuc、Ernst-Ulrich Würthwein、Bernhard Wünsch

  DOI：10.1039/d3ob01169k

  日期：——

  hydroxymethyl piperidines 21a,b–25a,b showing low nanomolar σ1 affinity (Ki < 100 nM). trans-Configured ligands (a-series) showed higher or equal σ1 affinity and higher selectivity over σ2 receptors and GluN2B-NMDA receptors than their cis-configured analogs (b-series). The additional hydroxymethyl moiety brings the log D7.4 value in a promising range. The high σ1 affinity (Ki = 3.6 nM) and the low lipophilicity

  螺环支架在药物发现中发挥着越来越重要的作用，因为它们定义了刚性的三维空间以增加与蛋白质结合位点的特异性相互作用。在此，将螺环中心引入先导化合物1中以使其柔性的苄氨基乙基侧链刚性化。合成的关键步骤是不同的α,β-不饱和酰胺6和13-16与丙烯酸甲酯在TBDMSOTf存在下的反应。DFT 计算将这种转变的机制解释为协同 Diels-Alder 反应（泛函 B3LYP 和 TPSS）或双 (aza)-Michael 加成（泛函 PBE 和 wB97X-D）。分离非对映体螺环产物8和17–20后，LiAlH 4还原得到螺环羟甲基哌啶21a,b–25a,b，显示出低纳摩尔σ 1亲和力（K i < 100 nM）。与顺式配置的类似物（b系列）相比，反式配置的配体（a系列）对σ2受体和GluN2B-NMDA受体表现出更高或相等的σ1亲和力和更高的选择性。额外的羟甲基部分使 log  D 7.4值处于一个有希望的范围内。高σ
• Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents
  作者：Justin S. Bryans、Natasha Davies、Nicolas S. Gee、Visaka U. K. Dissanayake、Giles S. Ratcliffe、David C. Horwell、Clare O. Kneen、Andrew I. Morrell、Ryszard J. Oles、John C. O'Toole、Gemma M. Perkins、Lakhbir Singh、Nirmala Suman-Chauhan、Jacqueline A. O'Neill

  DOI：10.1021/jm970649n

  日期：1998.5.1

  As part of a program to investigate the structure-activity relationships of Gabapentin (Neurontin), a number of alkylated analogues were synthesized and evaluated in vitro for binding to the Gabapentin binding site located on the alpha(2) delta subunit of a calcium channel. A number of other bridged and heterocyclic analogues are also reported along with their in vitro data. Two compounds showing higher affinity than Gabapentin were selected for evaluation in an animal model of epilepsy. One of these compounds, cis-(1S,3R)-(1-(aminomethyl)-3-methylcyclohexyl)acetic acid hydrochloride (19), was shown to be effective in this model with a profile similar to that of Gabapentin itself.