(E)-2-methyl-4-(p-tolyl)but-3-en-2-ol | 77144-23-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-2-methyl-4-(p-tolyl)but-3-en-2-ol
• 英文别名: (E)-2-methyl-4-(4-methylphenyl)but-3-en-2-ol
• CAS: 77144-23-1
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: WNURGMGERNKCCO-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-4-(p-tolyl)but-3-en-2-ol 在 五氟化锑 、 氟磺酸 作用下， 以 various solvent(s) 为溶剂， 生成 1-methyl-4-(3-methylbut-1-enyl)benzene
  参考文献：
  名称：

  Considered stable cations. 259. Application of the Gassman-Fentiman tool of increasing electron demand to the carbon-13 NMR spectroscopic study of 1-aryl-3-methylbut-2-enyl (allylic) and 2-arylpent-3-yn-2-yl (propargylic) cations

  摘要：

  DOI：

  10.1021/ja00299a030
• 作为产物：
  描述：

  2-甲基-4-(4-甲基苯基)丁-3-炔-2-醇 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 以85%的产率得到(E)-2-methyl-4-(p-tolyl)but-3-en-2-ol
  参考文献：
  名称：

  Highly Activated Vinyl Hydrogen in a Significantly Twisted Styrene

  摘要：

  The novel example of a vinylic hydrogen more reactive than a benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. In this paper, the full details of the examples of the highly activated vinyl hydrogens in twisted styrene derivatives are described, with a discussion on the correlation between the reactivity of the vinyl hydrogens and the magnitude of the twist. The highly reactive vinyl hydrogens could be rationalized by considering the novel orbital interaction between the pi* orbital of the benzene ring and the sigma orbital of the vinylic C-H bond in the twisted styrene derivatives.

  DOI：

  10.1021/jo061092z

文献信息

• Aqueous phase semihydrogenation of alkynes over Ni–Fe bimetallic catalysts
  作者：Rohit K. Rai、Mahendra K. Awasthi、Vipin K. Singh、Sudipta Roy Barman、Silke Behrens、Sanjay K. Singh

  DOI：10.1039/d0cy01153c

  日期：——

  Bimetallic Ni–Fe catalysts (Ni/Fe, 1 : 1, 1 : 3, and 3 : 1) are synthesized and explored for their catalytic activity in semihydrogenation of internal alkynes using H₂ gas in water–ethanol solution.

  双金属Ni-Fe催化剂（Ni/Fe，1：1，1：3和3：1）被合成并用于在水-乙醇溶液中使用H2气体对内部炔烃进行半加氢反应的催化活性研究。
• Process for the preparation of aryl substituted aldehydes, ketones and
  申请人：Givaudan Corporation

  公开号：US04070374A1

  公开（公告）日：1978-01-24

  Upon reacting an alcohol having an olefinic double bond with an aryl bromide or iodide in the presence of a Paladium catalyst, there is provided either an aryl substituted aldehyde, ketone or olefinic alcohol.

  在存在钯催化剂的情况下，将含有烯丙基双键的醇与芳基溴化物或碘化物反应，可以得到芳基取代的醛、酮或烯丙醇。
• Copper-catalyzed oxidative alkenylation of C(sp³)–H bonds via benzyl or alkyl radical addition to β-nitrostyrenes
  作者：Shengrong Guo、Yanqin Yuan、Jiannan Xiang

  DOI：10.1039/c4nj02416h

  日期：——

  A new method for the preparation of (E)-β-alkylstyrene derivatives has been developed via the addition of a benzyl or alkyl radical to β-nitrostyrenes using di-tert-butyl peroxide (DTBP) as the oxidant in the presence of Cu powder catalyst. The C–H bonds in various toluene derivatives, ethers, alkanes and alcohols were successfully converted into C–C bonds to yield the corresponding (E)-β-alkylstyrene

  通过在铜粉存在下，使用过氧化二叔丁基（DTBP）作为氧化剂，将苄基或烷基基团加到β-硝基苯乙烯中，已开发出一种新的（E）-β-烷基苯乙烯衍生物的制备方法。催化剂。各种甲苯衍生物，醚，烷烃和醇中的C–H键已成功转化为C–C键，从而以中等至良好的收率得到了相应的（E）-β-烷基苯乙烯衍生物。
• Selective Aerobic Oxygenation of Tertiary Allylic Alcohols with Molecular Oxygen
  作者：Bencong Zhu、Tao Shen、Xiaoqiang Huang、Yuchao Zhu、Song Song、Ning Jiao

  DOI：10.1002/anie.201903690

  日期：2019.8.5

  Aerobic epoxidation of tertiary allylic alcohols remains a significant challenge. Reported here is an efficient and highly chemoselective copper‐catalyzed epoxidation and semipinacol rearrangement reaction of tertiary allylic alcohols with molecular oxygen. The solvent 1,4‐dioxane activates dioxygen, thereby precluding the addition of a sacrificial reductant.

  叔烯丙醇的有氧环氧化仍然是一个重大挑战。此处报道了叔烯丙基醇与分子氧的高效且高度化学选择性的铜催化的环氧化和半频哪醇重排反应。溶剂1,4-二恶烷会激活双氧，从而排除了牺牲性还原剂的添加。
• Transition-Metal Catalyzed Stereoselective γ-Arylation and Friedel-Crafts Alkylation: A Concise Synthesis of Indenes
  作者：Karu Ramesh、Gedu Satyanarayana

  DOI：10.1002/ejoc.202000030

  日期：2020.6.16

  A concise synthesis of Mizoroki–Heck products and corresponding indenes starting with simple tert ‐alkenols and aryl halides is presented. Notably, the γ‐arylation was done under [Pd]‐catalysis by using water as the sole green solvent and the synthesis of indenes via acid‐mediated intramolecular Friedel–Crafts cyclization.

  介绍了从简单的叔烯醇和卤代芳基化合物开始的合成简单的Mizoroki-Heck产物和相应的茚满。值得注意的是，γ芳基化反应是在[Pd]催化下，以水为唯一的绿色溶剂，并通过酸介导的分子内Friedel-Crafts环化反应合成茚满。