trans-1,2-dimethyl-1-phenylcyclopentane | 56399-58-7

• 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: trans-1,2-dimethyl-1-phenylcyclopentane
• 英文别名: [(1R,2S)-1,2-dimethylcyclopentyl]benzene
• CAS: 56399-58-7；56421-25-1；56421-30-8；113427-81-9；113427-82-0；123121-28-8；123121-29-9
• 化学式: C₁₃H₁₈
• 分子量: 174.286
• InChiKey: OQWVSBQJVFKBCG-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5-溴-1-戊烯 在 甲醇 、 正丁基锂 作用下， 反应 1.5h， 生成 trans-1,2-dimethyl-1-phenylcyclopentane
  参考文献：
  名称：

  Original reactions of α,α-dithio aryl alkanes with butyllithiums

  摘要：

  Thioacetals derived from aromatic ketones react with butyllithiums already at -78-degrees-C and produce via a reductive process the corresponding alpha-thiobenzyllithiums in high yields. The same reaction also takes place selectively, under suitable conditions, with the thioacetals derived from benzaldehyde on which a competing metallation reaction is also possible. These observations clearly show that the thioacetal functionality is not a suitable protecting group against alkyllithiums for aromatic carbonyl compounds.

  DOI：

  10.1016/s0040-4039(00)74368-1

文献信息

• Synthesis of organolithium compounds from phenyl selenides
  作者：Alain Krief、Abdesslame Nazih、Myriam Hobe

  DOI：10.1016/0040-4039(95)01689-f

  日期：1995.10

  Alkyl aryl selenides react with lithium arenides to produce, regioselectively, alkyllithiums and lithium arylselenolates. Experimental conditions, especially the temperature, have a profound effect on the course of this reaction and on the nature of the products.

  烷基芳基硒化物与芳基锂反应生成区域选择性的烷基锂和芳基硒酸锂。实验条件，特别是温度，对该反应的过程和产物的性质具有深远的影响。
• Original syntheses of arylcycloalkanes
  作者：Alain Krief、Philippe Barbeaux

  DOI：10.1039/c39870001214

  日期：——

  Arylcycloalkanes have been prepared from acetophenone by a three-step sequence involving the synthesis of α-pheny(ω-alkenyl)methylselenides and their reaction with butyl-lithium reagents to give an intermediate which adds across the CC double bond to give 2-methyl-2-phenylcycloalkylmethyl-lithiums with stereocontrol; other syntheses of these compounds are also described.

  芳基环烷烃是由苯乙酮通过三步序列制备的，该过程涉及α-苯基（ω-烯基）甲基硒化物的合成及其与丁基锂试剂的反应，从而生成一种中间体，该中间体通过C C双键加成以生成2-甲基具有立体控制的-2-苯基环烷基甲基锂；还描述了这些化合物的其他合成。
• Stereochemical outcome of benzyllithiums synthesis from selenides
  作者：Alain Krief、Myriam Hobe、Willy Dumont、Elie Badaoui、Eric Guittet、Guy Evrard

  DOI：10.1016/s0040-4039(00)92094-x

  日期：1992.6

  Epimerisation usually occurs during the synthesis of arylalcanes from the corresponding benzylselenides which involves benzyllithiums as intermediates. This has been used to produce stereoselectively arylcyclopentanes and arylcyclopropanes. γ-Benzenesulfonyloxyalkyl selenides substituted on the carbon bearing the benzenesulfonyl group behave differently and lead stereospecifically to arylcyclopropane

  差向异构化通常发生在由相应的苄基硒化物合成芳基烷烃的过程中，该苄基硒化物涉及苄基锂作为中间体。这已被用于生产立体选择性的芳基环戊烷和芳基环丙烷。在带有苯磺酰基的碳上取代的γ-苯磺酰基氧基烷基硒化物的行为不同，并且立体定向地引入芳基环丙烷衍生物。
• Stereoselective syntheses of 1,2-dialkyl-1-phenyl cyclopentanes involving intramolecular carbolithiation of olefins
  作者：Alain Krief、Benoît Kenda、Christophe Maertens、Bruno Remacle

  DOI：10.1016/0040-4020(96)00262-1

  日期：1996.5

  2-Ethyl-1-methyl-1-phenyl cyclopentane, unavailable by butyllithium-promoted carbocyclisation of the corresponding alkenyl selenide, has been efficiently produced using two different strategies involving the carbocyclisation of 6-phenyl-6-methylseleno-1-heptene as the key step.

  丁基锂促进相应环烯基硒化物的碳环化无法获得的2-乙基-1-甲基-1-苯基环戊烷已通过两种不同的策略有效生产，这些策略涉及6-苯基-6-甲基硒基-1-庚烯的碳环化。关键步骤。
• Intramolecular nucleophilic addition to unsaturated carbon. Dependence of cyclization efficiency on the method of carbon-carbon bond cleavage utilized to generate the reactive species
  作者：Leo A. Paquette、John P. Gilday、George D. Maynard

  DOI：10.1021/jo00282a019

  日期：1989.10