(3-(cyclohex-1-en-1-yl)propyl)benzene | 95062-99-0

• 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: (3-(cyclohex-1-en-1-yl)propyl)benzene
• 英文别名: 3-(Cyclohexen-1-yl)propylbenzene
• CAS: 95062-99-0
• 化学式: C₁₅H₂₀
• 分子量: 200.324
• InChiKey: YVMJULIRZGMYBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (3-(cyclohex-1-en-1-yl)propyl)benzene 以 环己烷 为溶剂， 生成
  参考文献：
  名称：

  Ellis-Davies, Graham C. R.; Gilbert, Andrew; Heath, Peter, Journal of the Chemical Society. Perkin transactions II, 1984, p. 1833 - 1842

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(((phenylsulfonyl)methyl)sulfonyl)pentan-1-ol 在 四(三苯基膦)钯 、 三丁基膦 、 palladium 10% on activated carbon 、 potassium tert-butylate 、 氢气 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙酸乙酯 、 苯 为溶剂， 反应 18.5h， 生成 (3-(cyclohex-1-en-1-yl)propyl)benzene
  参考文献：
  名称：

  通过Mitsunobu C-烷基化然后Ramberg-Bäcklund环收缩合成环烯烃

  摘要：

  环烯烃是通过一种新颖的合成方法制备的，该方法涉及以潜在的立体选择性方式形成两个C C键。第一键是通过采用Mitsunobu脱水的C-烷基形成的；第二个C C键涉及通过Ramberg-Bäcklund重排进行的环收缩。

  DOI：

  10.1016/j.tetlet.2018.06.014

文献信息

• β- and γ-Disubstituted Olefins: Substrates for Copper-Catalyzed Asymmetric Allylic Substitution
  作者：Caroline A. Falciola、Karine Tissot-Croset、Hugo Reyneri、Alexandre Alexakis

  DOI：10.1002/adsc.200800086

  日期：2008.5.5

  The copper-catalyzed asymmetric allylic alkylation has shown through many examples that it is a powerful means to generate stereogenic centers with mono β- and γ-substituted olefinic substrates. However, little has been reported about more substituted olefinic patterns, such as β-disubstituted allylic electrophiles. In this paper, we show that a simple procedure using easily accessible Grignard reagents

  铜催化的不对称烯丙基烷基化通过许多实例表明，它是用单β-和γ-取代的烯烃底物生成立体异构中心的有效手段。然而，关于更多取代的烯烃图案，例如β-二取代的烯丙基亲电试剂，几乎没有报道。在本文中，我们表明，使用容易获得的格氏试剂和低至3 mol％的铜/配体的简单程序可以促进高至近乎完美的对映选择性（高达> 99％ee），并且在很宽的范围内具有很好的γ选择性一组脂族或芳族β-二取代底物。
• Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides
  作者：Jicheng Duan、Yun-Fei Du、Xiaobo Pang、Xing-Zhong Shu

  DOI：10.1039/c9sc03347e

  日期：——

  providing facile access to important building blocks. We also demonstrated the possibility to apply this method for late-stage modification of peptides. A broad range of functionalized alkyl groups could be selectively introduced into tyrosine in peptides via C–C bond formation, which has been a challenge to the existing procedures.

  我们在这里报告了乙烯基/芳基和烷基 C-O 亲电子试剂之间的偶联反应，这些反应可以衍生自化学原料和天然存在的官能团。该方法提供了合成各种官能化和/或仲烷基取代的环烯烃的有效方法。这些化合物很难通过常规方法生产。该反应底物范围广泛，可耐受多种官能团，如醇、醛、酮、酯、酰胺、烯烃、炔烃、杂环、有机锡和有机硅化合物。该方法的综合效用已通过提供对重要构建块的便捷访问得到证明。我们还证明了将该方法应用于肽后期修饰的可能性。通过C-C键的形成，可以将多种官能化烷基选择性地引入肽中的酪氨酸中，这对现有的方法是一个挑战。
• β-Disubstituted Allylic Chlorides: Substrates for the Cu-Catalyzed Asymmetric SN2′ Reaction
  作者：Caroline A. Falciola、Karine Tissot-Croset、Alexandre Alexakis

  DOI：10.1002/anie.200601855

  日期：2006.9.11
• Regio- and Enantioselective Substitution of Primary Endocyclic Allylic Sulfoximines with Organocopper and Organocuprate Reagents. The Importance of Iodide for the Allylic Substitution with Organocopper Compounds
  作者：Hans-Joachim Gais、Harald Mueller、Joerg Bund、Matthias Scommoda、Jochen Brandt、Gerhard Raabe

  DOI：10.1021/ja00114a009

  日期：1995.3

  The endocyclic N-substituted allylic sulfoximines 17-20 and 26 were synthesized from the corresponding cycloalkanones and the various (S)-S-(lithiomethyl)-S-phenylsulfoximine in enantiomerically pure form in yields of 60-70% in a process involving the isomerization of the intermediate vinylic sulfoximines. Desilylation of 26 gave the parent N-H sulfoximine 27 from which the N-sulfonylsulfoximines 28 and 29 were prepared. The X-ray crystal structure of 28 was determined. The allylic sulfoximines 17-20 and 26-29 did not racemize or rearrange thermally to the corresponding allylic sulfinamides. Reaction of the allylic sulfoximines 18, 28, and 29 with the organocuprate reagents 2/LiI, 35/LiI, and 47/LiI led with alpha-selectivities of 92:8 to 99:1 to the endocyclic alkenes 39 in good to high yields. Reaction of 17-20, 28, and 29 with the organocopper reagents 5/LiI, 30/LiI, 31/LiI, 32/LiI, 33/LiI, 34/LiI, and 37/LiI in the presence of BF3 resulted in the formation of the exocyclic alkenes 38, 41, 43, and 45, respectively, in good to high yields with gamma-selectivities of 80:20 to 99:1. The sulfonimidoyl group imparts asymmetric induction to the substitution in the range of 27-90% ee. The (S)-sulfonimidoyl group leads to a preferential bond formation from the si side of the double bond. From the sulfoximines 18 and 26-29 the N-methylsulfoximine 18 and the N-tosylsulfoximine 28 showed the highest and lowest reactivity with the butylcopper reagent 32/LiI in the presence of BF3 respectively, while in the absence of BF3 only 29 reacted. The Lewis acid most likely serves to activate the N-methyl- and N-tosylsulfoximines or intermediates thereof through coordination at the sulfonimidoyl and sulfonyl group. Reaction of the sulfoximines 18 and 29 with pure Me(3)SiCH(2)Cu (34) revealed a strong rate acceleration by LiI and an even stronger one by Bu(4)NI. This points to the existence of a heteroleptic cuprate or a related compound as reactive species. In substitutions with the Yamamoto reagents RCu/MX/BF3, the halide is important and a reaction between RCu and BF3 does not have, at least in the case of allylic sulfoximines, to be invoked. In reactions of 17-20 besides the alkenes, the sulfinamide ent-4 was formed with an ee value of 97% in high yield with retention of configuration. The absolute configuration of the exocyclic alkenes 38, 41, and 45 was determined by ozonolysis to the corresponding cycloalkanones followed by their conversion to the corresponding lactones and/or CD measurement of the former.
• Stereospecific Ni-Catalyzed Cross-Coupling of Potassium Alkenyltrifluoroborates with Alkyl Halides
  作者：Gary A. Molander、O. Andreea Argintaru

  DOI：10.1021/ol500408a

  日期：2014.4.4

  A general method for the alkenylation of alkyl electrophiles using nearly stoichiometric amounts of the air- and moisture-stable potassium organotrifluoroborates has been developed. Various functional groups were tolerated on both the nucleophilic and electrophilic partner. Reactions of highly substituted E- and Z-alkenyltrifluoroborates, as well as vinyl- and propenyltrifluoroborates, were successful, and no loss of stereochemistry or regiochemistry was observed.