1-(1Z)-1-hexen-1-yl-4-methylbenzene | 56949-84-9

• 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: 1-(1Z)-1-hexen-1-yl-4-methylbenzene
• 英文别名: (Z)-1-(hex-1-enyl)-4-methylbenzene；(Z)-1-(4-methylphenyl)-1-hexene；1-[(Z)-hex-1-enyl]-4-methylbenzene
• CAS: 56949-84-9
• 化学式: C₁₃H₁₈
• 分子量: 174.286
• InChiKey: BPNRCAKPBNDWPB-SREVYHEPSA-N

物化性质

• 沸点：
  257.1±10.0 °C(Predicted)
• 密度：
  0.888±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1-(1Z)-1-hexen-1-yl-4-methylbenzene 在 bis(acetylacetonate)nickel(II) 、 二异丁基氢化铝 、 4-甲基苯硼酸新戊基二醇酯 、 三环己基膦 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 16.0h， 以66%的产率得到1-(1E)-1-hexen-1-yl-4-methylbenzene
  参考文献：
  名称：

  Highly E-Selective, Stereoconvergent Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkenyl Ethers

  摘要：

  An improved method for the nickel-catalyzed Suzuki-Miyaura cross-coupling of alkenyl ethers is reported. This stereoconvergent protocol allows for the utilization of a wide range of alkenyl ethers and aryl boronic esters for the synthesis of variously substituted styrene derivatives. An olefinic mixture with respect to the alkenyl ethers can be employed, thereby circumventing the stereodefined synthesis of starting materials. Preliminary mechanistic investigations indicate a nickel-catalyzed olefin isomerization following initial stereoretentive cross-coupling.

  DOI：

  10.1021/acs.orglett.9b00946
• 作为产物：
  描述：

  1-(p-tolyl)-1-hexyne 在 [(6-Mes)Cu(OtBu)] 作用下， 以 氘代苯 、 叔丁醇 为溶剂， 反应 24.0h， 以97%的产率得到1-(1Z)-1-hexen-1-yl-4-methylbenzene
  参考文献：
  名称：

  铜-NHC介导的炔烃的半氢化和氢硼化：使用环扩碳烯的增强的催化活性。

  摘要：

  由（NHC）CuMes与t BuOH质子分解制得的一系列带有五元，六元和七元环N-杂环卡宾的二配位叔丁醇铜配合物已被用作苯甲酸半加氢反应的催化前体。炔烃与硅烷/ t BuOH的混合，以及炔烃与HBPin的硼氢化。两种方法都具有较高的区域选择性，并显示六元和七元环卡宾具有增强作用。

  DOI：

  10.1021/acs.organomet.8b00467

文献信息

• General Copper-Catalyzed Coupling of Alkyl-, Aryl-, and Alkynylaluminum Reagents with Organohalides
  作者：Bijay Shrestha、Surendra Thapa、Santosh K. Gurung、Ryan A. S. Pike、Ramesh Giri

  DOI：10.1021/acs.joc.5b02077

  日期：2016.2.5

  We report the first example of a very general Cu-catalyzed cross-coupling of organoaluminum reagents with organohalides. The reactions proceed for the couplings of alkyl-, aryl-, and alkynylaluminum reagents with aryl and heteroaryl halides and vinyl bromides, affording the cross-coupled products in good to excellent yields. Both primary and secondary alkylaluminum reagents can be utilized as organometallic

  我们报道了有机铝试剂与有机卤化物非常普通的铜催化交叉偶联的第一个例子。进行反应以使烷基铝，芳基铝和炔基铝试剂与芳基和杂芳基卤化物和乙烯基溴化物偶联，从而以良好或优异的收率提供交叉偶联的产物。伯烷基铝试剂和仲烷基铝试剂都可用作有机金属偶联剂。这些反应不会因β-氢化物的消除而复杂化，因此，即使在“无配体”条件下与杂芳基卤化物偶合，也不会用仲烷基铝试剂观察到重排产物。自由基探针的自由基时钟实验和Ph 3的相对反应性研究具有两个不同氧化还原电位的具有两个卤代芳烃1-溴萘和4-氯苄腈的Al表明该反应不涉及作为中间体的游离芳基和自由基阴离子。这些结果与通过使Ph 3 Al与含有p -H，p -Me，p -F和p -CF 3取代基的碘代芳烃反应获得的哈米特图的结果结合在一起，该曲线显示出一条线性曲线（R 2 = 0.99）。 ρ值为+1.06，表明电流转换遵循氧化加减还原途径。
• Metal‐Catalyzed Remote Functionalization of ω‐Ene Unsaturated Ethers: Towards Functionalized Vinyl Species
  作者：Guo‐Ming Ho、Lina Judkele、Jeffrey Bruffaerts、Ilan Marek

  DOI：10.1002/anie.201802434

  日期：2018.7.2

  The combined ruthenium‐catalyzed chain walking with the nickel‐catalyzed cross‐coupling reaction of ω‐alkenyl ethers provide a unique entry to functionalized vinyl species. This transformation illustrates the power and flexibility of remote functionalization by demonstrating the compatibility of two independent reactions involving unrelated sites.

  钌催化的链走与ω-烯基醚的镍催化的交叉偶联反应相结合，为官能化乙烯基物种提供了独特的入口。此转换通过演示涉及无关位点的​​两个独立反应的兼容性，说明了远程功能化的功能和灵活性。
• Highly selective coupling of organoboron compounds via oxovanadium(V)-induced oxidation
  作者：Takuji Ishikawa、Suguru Nonaka、Toshikazu Hirao

  DOI：10.1039/a801844h

  日期：——

  Reaction of organoboranes or organoborane ate complexes (obtained by treatment with BunLi or CsF) with oxovanadium(V) compounds results in the intramolecular oxidative coupling of organic groups on the boranes or borates.

  有机硼烷或有机硼烷ate络合物（通过硼酸或铯硼处理获得）与氧钒（V）化合物反应，会导致硼烷或硼酸盐上的有机基团发生分子内氧化偶联。
• Ir-Catalyzed Distal Branch-Selective Hydroarylation of Unactivated Internal Alkenes with Benzanilides via C–H Activation along with Consecutive Isomerization
  作者：King Hung Nigel Tang、Ryo Tokutake、Mamoru Ito、Takanori Shibata

  DOI：10.1021/acs.orglett.3c01619

  日期：2023.7.21

  We herein report a synergistic strategy of C–H activation and consecutive isomerization catalyzed by an Ir catalyst to selectively obtain branched isomers as C–H alkylated products of benzanilide derivatives. A well-tuned ligand and a directing group are crucial to achieve this selectivity. The scope of this reaction is demonstrated by the use of a variety of substituents and complex molecules.

  我们在此报告了一种由Ir催化剂催化的C-H活化和连续异构化的协同策略，以选择性地获得支化异构体作为苯甲酰苯胺衍生物的C-H烷基化产物。良好调节的配体和导向基团对于实现这种选择性至关重要。该反应的范围通过使用各种取代基和复杂分子来证明。
• Tellurium in Organic Synthesis. Preparation of <i>Z</i>-Vinylic Cuprates from <i>Z</i>-Vinylic Tellurides and Their Reaction with Enones and Epoxides
  作者：Fábio C. Tucci、André Chieffi、João V. Comasseto、Joseph P. Marino

  DOI：10.1021/jo951547c

  日期：1996.1.1

  Z-Vinylic tellurides, obtained with 100% stereoselectivity by the hydrotelluration of acetylenes, are easily transformed into Z-vinylic higher order cyanocuprates by reaction with preformed Me(2)Cu(CN)Li-2, n-Bu(2)Cu(CN)Li-2, or n-Bu(2-Th)Cu(CN)Li-2, with total retention of the double-bond configuration. The resulting vinylic higher order cyanocuprates react with unhindered enones to give the corresponding 1,4-addition products in good yields. Reaction of the vinylic higher order cyanocuprates with monosubstituted epoxides at 0 degrees C gives the homoallylic alcohols resulting from the attack to the less-substituted carbon atom, while the disubstituted epoxides failed to react. Allylic epoxides react at -78 degrees C with the vinylic higher order cyanocuprates to give mixtures of 1,2- and 1,4-opening products, the 1,4-product predominating. In all cases the double-bond configuration of the original vinylic telluride was preserved. The vinylic cuprates derived from simple vinylic tellurides and conjugated 1-telluroenynes react with epoxides at 0 degrees C, while vinylic cuprates derived from conjugated 1-tellurodienes required the addition of 1 equiv of BF3 . Et(2)O to give the homoallylic alcohols on reaction with epoxides. The opening of optically pure epoxides through tellurium/copper transmetalation is stereospecific, giving one single stereoisomer of the corresponding homoallylic alcohol.