(Z)-β-(cyclohexylmethyl)styrene

• 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: (Z)-β-(cyclohexylmethyl)styrene
• 英文别名: (Z)-1-cyclohexyl-2-phenylpropene；1-cyclohexyl-2-phenyl-1-pentene；[(Z)-1-cyclohexylprop-1-en-2-yl]benzene
• 化学式: C₁₅H₂₀
• 分子量: 200.324
• InChiKey: KKEDLCPJIGVGBH-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  15
• 可旋转键数：
  2
• 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

• 作为产物：
  描述：

  1-(1-phenylethyl)-1H-benzo[d][1,2,3]triazole 在 正丁基锂 、 四氯化钛 、 铜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 (Z)-β-(cyclohexylmethyl)styrene
  参考文献：
  名称：

  Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation

  摘要：

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.

  DOI：

  10.1021/jo980616v

文献信息

• Generation of magnesium carbenoids from 1-chloroalkyl phenyl sulfoxides with a Grignard reagent and applications to alkylation and olefin synthesis
  作者：Tsuyoshi Satoh、Atsushi Kondo、Jun Musashi

  DOI：10.1016/j.tet.2004.04.063

  日期：2004.6

  Treatment of 1-chloroalkyl phenyl sulfoxides with a Grignard reagent at low temperature gave magnesium carbenoids in quantitative yields. The generated magnesium carbenoids were found to be stable at lower than −60 °C for long periods of time and are reactive with Grignard reagents to give alkylated products. The reaction of the generated magnesium carbenoids with various kinds of lithium α-sulfonyl

  用格氏试剂在低温下处理1-氯烷基苯基亚砜，得到定量产率的镁类胡萝卜素。已发现生成的镁类胡萝卜素在低于-60°C的温度下可长期稳定，并且可与格氏试剂反应生成烷基化产物。生成的镁类胡萝卜素与各种锂α-磺酰基碳负离子的反应产生了具有良好碳收率的碳-碳键形成烯烃。该方法为制备烯烃提供了一种很好的方法。描述了上述反应的范围和限制。
• Copper catalyzed direct alkenylation of simple alkanes with styrenes
  作者：Yefeng Zhu、Yunyang Wei

  DOI：10.1039/c4sc00093e

  日期：——

  A novel Cu-catalyzed direct alkenylation of simple alkanes with styrenes was described. In the presence of a catalytic amount of Cu(OTf)2, a diverse range of alkenes undergo coupling with cycloalkanes to produce (E)-alkyl alkenes. This transformation is proposed to proceed via a radical process.

  报道了一种新型的铜催化的简单烷烃与苯乙烯的直接烯基化反应。在催化量的Cu(OTf)2存在下，多种烯烃与环烷烃进行耦合，生成（E）-烷基烯烃。据推测，这一转化过程通过自由基途径进行。
• Stereospecific Synthesis of Alkenes by Eliminative Cross-Coupling of Enantioenriched sp³ -Hybridized Carbenoids
  作者：Zhenhua Wu、Xun Sun、Kristin Potter、Yang Cao、Lev N. Zakharov、Paul R. Blakemore

  DOI：10.1002/anie.201606641

  日期：2016.9.26

  1‐Aryl‐1,2‐dialkylethenes were generated by a sequence of electrophilic substitution, 1,2‐metalate rearrangement, and β‐elimination initiated by the addition of enantioenriched α‐(carbamoyloxy)alkylboronates to enantioenriched lithiated carbamates. The carbenoid stereochemical pairing [i.e., “like”=(S)+(S) or “unlike”=(S)+(R)] and the elimination mechanism (syn or anti), not substituent effects, determined

  1-芳基1,2-二烷基乙烯是通过一系列亲电取代，1,2-金属盐重排以及通过将对映体富集的α-（氨基甲酰氧基）烷基硼酸酯添加到对映体富集的锂化氨基甲酸酯中而引发的β-消除。所述卡宾立体化学配对[即，“像” =（小号）+（小号）或“不同于” =（小号）+（[R）〕和消除机构（顺式或反），而不是取代基的影响，确定的配置三取代烯烃目标。例如，（Z）-2,5-二苯基-2-戊烯的产率为70％，其中E / Z = 5：95类似于Li和B的类胡萝卜素的结合以及顺式（热）消除，而E 异构体的收率相同，E / Z > 98：2，是通过其他相同的方法进行的，涉及立体化学配对不同。详细阐述的概念克服了直接连接烯烃合成的传统策略的固有局限性，除非将烯烃取代基进行强烈区分，否则传统策略无法实现有意义的立体化学偏向。
• Palladium-catalyzed intermolecular Heck reaction of alkyl halides
  作者：Yinjun Zou、Jianrong (Steve) Zhou

  DOI：10.1039/c4cc00297k

  日期：——

  An efficient Pd-catalyzed method for intermolecular Heck reaction of common alkyl halides is described for the first time.

  第一次描述了一种高效的Pd催化方法，用于常见烷基卤代烃的分子间Heck反应。
• Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation
  作者：Alan R. Katritzky、Dai Cheng、Scott A. Henderson、Jianqing Li

  DOI：10.1021/jo980616v

  日期：1998.9.1

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.