(E)-(4-methylpent-2-en-2-yl)benzene | 70303-26-3

• 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: (E)-(4-methylpent-2-en-2-yl)benzene
• 英文别名: (1,3-Dimethyl-1-butenyl)benzene；[(E)-4-methylpent-2-en-2-yl]benzene
• CAS: 70303-26-3
• 化学式: C₁₂H₁₆
• 分子量: 160.259
• InChiKey: ORWUYEJTGRNCKK-PKNBQFBNSA-N

物化性质

• 沸点：
  218.7±7.0 °C(Predicted)
• 密度：
  0.872±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (E)-(4-methylpent-2-en-2-yl)benzene 、 乙酸酐 在 selenium(IV) oxide 作用下， 生成 1-acetoxy-4-methyl-2-phenylpent-2-ene
  参考文献：
  名称：

  Morimoto, Takashi; Hirano, Masao; Koyama, Tsuyoshi, Journal of the Chemical Society. Perkin transactions II, 1985, p. 1109 - 1116

  摘要：

  DOI：
• 作为产物：
  描述：

  3-羟基-4-甲基-2-苯基戊-1-烯 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 苯 为溶剂， 反应 25.0h， 生成 (E)-(4-methylpent-2-en-2-yl)benzene
  参考文献：
  名称：

  A convergent method for the stereoselective synthesis of trisubstituted alkenes

  摘要：

  A method for the stereoselective, convergent synthesis of trisubstituted alkenes has been developed. The procedure features the synthesis of allylic alcohols 9 by coupling an aldehyde with a vinyl organometallic reagent. Treatment of 9 with carbon disulfide and methyl iodide gave the intermediate allylic xanthates 10 that underwent facile [3,3]-sigmatropic rearrangement to give the dithiocarbonates 11 and 12, radical reduction of which gave the (E)-alkenes 13 as the major products.

  DOI：

  10.1021/jo00035a004

文献信息

• Asymmetric induction—V
  作者：Christine Zioudrou、Irene Moustakali-Mavridis、Polyxene Chrysochou、Gerasimos J. Karabatsos

  DOI：10.1016/0040-4020(78)87014-8

  日期：1978.1

  The diastereomeric product ratios from reactions involving the addition of various reagents to the carbonyl of φCH3HC-COR compounds varies over a wide range. This variation is interpreted as due partly to changes in the structure of the diastereomeric transition states with changes in the size of R. For example, when R is smaller than the φCH3HC group the diastereomeric product ratios are close to

  从包括添加各种试剂的至φCH的羰基反应的非对映体产品比率3 HC-COR的化合物而变化在大范围内。这种变化被解释为部分由于变化的非对映体的过渡态的结构与R的大小例如变化，当R大于φCH较小3 HC组非对映体产物的比率接近那些在假设预测即1和2是最小能量非对映体的过渡态; 以及当R大于φCH更大3 HC基，非对映体产物的比率是大的，更接近那些人们可能预期，如果5和6 是最小的能量跃迁状态。
• Highly Stereoselective Positional Isomerization of Styrenes <i>via</i> <scp>Acid‐Catalyzed</scp> Carbocation Mechanism
  作者：Xiao‐Si Hu、Jun‐Xiong He、Ying Zhang、Jian Zhou、Jin‐Sheng Yu

  DOI：10.1002/cjoc.202100218

  日期：2021.8

  The first transition metal-free highly stereoselective positional isomerization of various α-alkyl styrenes through a carbocation mechanism triggered strategy is developed by using Al(OTf)3 as a hidden Brønsted acid catalyst, which provides facile access to value-added acyclic tri- and tetra-substituted alkenes in good yields with high stereoselectivity under mild conditions. The practicality of this

  通过使用 Al(OTf) 3作为隐藏的 Brønsted 酸催化剂，通过碳阳离子机制触发的策略开发了第一个无过渡金属的各种 α-烷基苯乙烯的高度立体选择性位置异构化，这为获得增值的无环三-和在温和条件下以高立体选择性和高收率制备四取代烯烃。该协议的实用性由克级合成、高立体选择性、良好的官能团耐受性和简单的操作进一步突出。机理研究支持 Al(OTf) 3充当隐藏的布朗斯台德酸催化剂并形成碳正离子中间体。
• Iron Catalyzed Isomerization of <scp>α‐Alkyl</scp> Styrenes to Access Trisubstituted Alkenes
  作者：Songgen Xu、Guixia Liu、Zheng Huang

  DOI：10.1002/cjoc.202000492

  日期：2021.3

  supported by phosphine‐pyridine‐oxazoline (PPO) ligand. The protocol provides an atom‐efficient and operationally simple approach to trisubstituted alkenes in high yields with excellent regio‐ and stereoselectivities under mild conditions. The results of deuterium‐labelling and radical trap experiments are consistent with an iron‐hydride pathway involving reversible alkene insertion and β‐H elimination.

  α-烷基苯乙烯的立体选择性异构化是通过使用膦-吡啶-恶唑啉（PPO）配体支持的新型铁催化剂完成的。该协议提供了一种原子效率高且操作简单的方法，可在温和条件下以高收率和出色的区域选择性和立体选择性对三取代烯烃进行生产。氘标记和自由基陷阱实验的结果与涉及可逆烯烃插入和β-H消除的铁氢化物途径一致。
• Copper-Catalyzed Decarboxylative C(sp² )-C(sp³ ) and C(sp)-C(sp³ ) Coupling of Substituted Cinnamic Acids and 3-Phenyl Propiolic Acid with N-Tosyl Oxaziridines
  作者：Bich-Ngoc Nguyen、Hai-Thuong Cao

  DOI：10.1002/ejoc.201900982

  日期：2019.9.15

  We describe the copper‐catalyzed decarboxylative alkylation of substituted cinnamic acids using N‐Tosyl oxaziridines with high yields and excellent stereoselectivities. The (E)‐alkene was achieved as the sole isomer in a single step. Our protocol also gives an efficient approach for the construction of alkyl phenyl acetylenes without oxidants and bases. Initial investigation suggested a radical process

  我们描述了使用N-甲苯磺酰氧氮丙啶具有高收率和优异的立体选择性的铜催化的取代肉桂酸脱羧烷基化反应。（E）-烯烃是一步完成的唯一异构体。我们的协议还为构建没有氧化剂和碱的烷基苯基乙炔提供了一种有效的方法。初步调查表明，涉及到一个激进的过程。
• Rhodium‐Catalyzed Regio‐ and Diastereoselective [3+2] Cycloaddition of <i>gem</i>‐Difluorinated Cyclopropanes with Internal Olefins
  作者：Yaxin Zeng、Ying Xia

  DOI：10.1002/anie.202307129

  日期：2023.8.7

  A rhodium-catalyzed [3+2] cycloaddition reaction between readily available gem-difluorinated cyclopropanes and internal olefins has been developed, providing a wide range of multisubstituted gem-difluorinated cyclopentanes. This reaction shows an example where the “CF2” motif can be kept upon ring extension. The process is atom-economic and allows to reach numerous gem-difluorinated cyclopentanes with

  已经开发了易于获得的偕二氟化环丙烷和内烯烃之间的铑催化[3+2]环加成反应，提供了多种多取代偕二氟化环戊烷。该反应显示了“CF 2 ”基序可以在环延伸时保留的例子。该方法是原子经济的，并且可以得到许多具有良好区域选择性和非对映选择性的偕二氟化环戊烷。