(3Z)-2-methyl-4-(4-methylphenyl)-3-buten-2-ol | 334875-18-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (3Z)-2-methyl-4-(4-methylphenyl)-3-buten-2-ol
• 英文别名: (Z)-2-methyl-4-(4-methylphenyl)but-3-en-2-ol
• CAS: 334875-18-2
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: WNURGMGERNKCCO-HJWRWDBZSA-N

物化性质

• 沸点：
  297.1±9.0 °C(Predicted)
• 密度：
  0.994±0.06 g/cm3(Predicted)

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：

  (3Z)-2-methyl-4-(4-methylphenyl)-3-buten-2-ol 在 正丁基锂 、 四甲基乙二胺 、 potassium tert-butylate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 生成 1-[(E)-1-deuterio-3-methoxy-3-methylbut-1-enyl]-4-methylbenzene
  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
• 作为产物：
  描述：

  2-甲基-4-(4-甲基苯基)丁-3-炔-2-醇 在 palladium on activated charcoal 喹啉 、 氢气 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以72%的产率得到(3Z)-2-methyl-4-(4-methylphenyl)-3-buten-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。
• Photoredox/Nickel Dual Catalysis-Enabled Modular Synthesis of Arylallyl Alcohols with Acetylene as the Two-Carbon Synthon
  作者：Kangkui Li、Xianyang Long、Shifa Zhu

  DOI：10.1021/acscatal.2c06178

  日期：2023.2.17

  alcohols were synthesized in an acetylene atmosphere (1 atm). This method features broad substrate scopes, good functional group tolerance, and high Z-selectivity. In addition to the intermolecular difunctionalization of acetylene, the reaction is also amenable to intramolecular ring formation, giving highly valuable indenols and indanones. The mechanistic investigation indicates that the alkenylnickel

  芳基烯丙醇常见于天然产物和药物分子中。传统的合成主要依赖于使用预合成烯烃的双组分反应。在此，我们报告了一种光氧化还原/镍双催化三组分交叉偶联反应，该反应能够使用乙炔快速合成芳基烯丙醇作为双碳 (C2) 合成子。在该反应中，芳基卤化物和羰基化合物以乙炔作为连接基团缝合在一起。在乙炔气氛 (1 atm) 中合成了一系列芳基烯丙醇。该方法具有底物适用范围广、官能团耐受性好、Z高等特点-选择性。除了乙炔的分子间双官能化外，该反应还适用于分子内环的形成，得到非常有价值的茚酚和茚满酮。机理研究表明烯基镍是关键的中间体。该中间体可以被认为是一种替代的烯基格氏试剂，但具有更好的官能团相容性。以该方法为关键步骤，制备了包括天然产物和药物分子在内的几个重要分子。
• Vinyl hydrogen more reactive than benzyl hydrogen toward base in significantly twisted styrenes
  作者：Hajime Mori、Takafumi Matsuo、Yasunori Yoshioka、Shigeo Katsumura

  DOI：10.1016/s0040-4039(01)00308-2

  日期：2001.4

  The novel example of vinyl hydrogen more reactive than benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. The characteristic nature of the vinyl hydrogen, which is activated by sigma-pi* orbital interaction, was apparently demonstrated. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Reactions of vinyltributylgermanes and aryl halides under Heck conditions
  作者：Nicole M. Torres、Jérôme M. Lavis、Robert E. Maleczka

  DOI：10.1016/j.tetlet.2009.05.035

  日期：2009.8

  We describe the palladium-mediated reaction of vinyltributylgermanes with aryl halides under Heck conditions. Depending on their degree of substitution, (E)-vinyltributylgermanes preferentially afford either the cine or Z-alkenyl coupled products in moderate yields. Substituents at the allylic position, especially oxygen, impact regio- and stereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.
• Highly Activated Vinyl Hydrogen in a Significantly Twisted Styrene
  作者：Hajime Mori、Takafumi Matsuo、Yasunori Yoshioka、Shigeo Katsumura

  DOI：10.1021/jo061092z

  日期：2006.11.1

  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.