(E)-2,6-di-tert-butyl-4-styrylphenol | 21449-69-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2,6-di-tert-butyl-4-styrylphenol
• 英文别名: trans-3,5-Di-tert-butyl-4-stilben-ol；2,6-ditert-butyl-4-[(E)-2-phenylethenyl]phenol
• CAS: 21449-69-4
• 化学式: C₂₂H₂₈O
• 分子量: 308.464
• InChiKey: STLOQHDLBLPKOZ-OUKQBFOZSA-N

物化性质

• 熔点：
  85-88 °C
• 沸点：
  393.4±37.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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)-2,6-di-tert-butyl-4-styrylphenol 在 Co(Salpr) 、 氧气 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.7h， 生成 1-(3,5-二叔丁基-4-羟基苯基)-1-丙醇
  参考文献：
  名称：

  Oxygenation of tert-butylphenols with an unsaturated side chain

  摘要：

  DOI：

  10.1021/jo00362a018
• 作为产物：
  描述：

  3,5-二叔丁基-4-羟基苯甲醛 在 potassium tert-butylate 、 氧气 、 溶剂黄146 作用下， 以 乙醚 、 正己烷 、 叔丁醇 为溶剂， 反应 5.84h， 生成 (E)-2,6-di-tert-butyl-4-styrylphenol
  参考文献：
  名称：

  Oxygenation of tert-butylphenols with an unsaturated side chain

  摘要：

  DOI：

  10.1021/jo00362a018

文献信息

• Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers
  作者：Kevin J. Romero、Matthew S. Galliher、Mark A. R. Raycroft、Jean‐Philippe R. Chauvin、Irene Bosque、Derek A. Pratt、Corey R. J. Stephenson

  DOI：10.1002/anie.201810870

  日期：2018.12.21

  functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical-trapping antioxidants; more so than the phenols from

  据报导一种简单的方法使苯丙烯类衍生物二聚。它利用对位不饱和酚的电化学氧化，以仿生方式进入二聚体材料。转化的温和性质提供了出色的官能团耐受性，从而形成了一种统一的方法，用于合成一系列具有出色区域控制能力的天然产物和相关类似物。该方法操作简单，可以提高合成复杂天然产物的效率。有趣的是，醌甲基二聚体中间体是有效的自由基捕获抗氧化剂。尽管它们不具有不稳定的H原子转移到传播自氧化的过氧自由基上，但比衍生或转化它们的酚更重要。
• Oxygenation of (E)-4-stilbenols catalysed by cobalt(II) schiff base chelates
  作者：P.A. Ganeshpure、S. Satish

  DOI：10.1016/s0040-4039(00)82415-6

  日期：1988.1

  Cobalt(II) Schiff base chelate, CoSMDPT (1), catalysed 'the oxygenation of (E)-4-stilbenols (2a–2d), to give two molecules of aldehydes. Both the oxygen atoms of dioxygen are incorporated into the substrate, providing a good chemical model for dioxygenase reactions.

  钴（II）席夫碱螯合物CoSMDPT（1）催化（E）-4-芪苯酚（2a–2d）的氧合，得到两个醛分子。双氧的两个氧原子都结合到底物中，为双氧酶反应提供了良好的化学模型。
• Controlled Aerobic Oxidative Dimerization of Hydroxystilbenoids by Chromium Catalysis
  作者：Shota Nagasawa、Yudai Itagaki、Yusuke Sasano、Yoshiharu Iwabuchi

  DOI：10.1021/acs.orglett.4c00839

  日期：2024.5.24

  Aerobic oxidative dimerization of hydroxystilbenoids is described. A Cr–salen complex catalyzed the dimerization of hydroxystilbenoids in 1,1,1,3,3,3-hexafluoroisopropanol to form compounds comprising a natural product-like scaffold (quadrangularin) or its precursor depending on the aromatic substituents. The addition of a catalytic amount of scandium triflate [Sc(OTf)3] to the reaction system altered

  描述了羟基二苯乙烯类化合物的有氧氧化二聚。 Cr-salen 络合物催化 1,1,1,3,3,3-六氟异丙醇中羟基二苯乙烯类化合物的二聚，形成包含天然产物样支架（四边形）或其前体（取决于芳香族取代基）的化合物。向反应体系中添加催化量的三氟甲磺酸钪[Sc(OTf) 3 ]改变了反应结果，得到了不同的天然产物样化合物，苍白球醇型二聚体。
• Co(salen)-Catalyzed <i>tert</i>-Butyl Hydroperoxide Oxidation of <i>tert-</i>Butylphenols Bearing an Unsaturated Side Chain
  作者：Kazushige Maruyama、Takahiro Kusukawa、Takahiro Mashino、Akira Nishinaga

  DOI：10.1021/jo950944k

  日期：1996.1.1

  Co(salen)-catalyzed oxidation of 2,4- and 2,6-di-tert-butylphenols bearing an unsaturated side chain, with tert-butyl hydroperoxide (TBHP) in CH2Cl2 at rt, results predominantly in the formation of tert-butylperoxylated products. The position of tert-butylperoxylation depends on the nature of the unsaturated side chain: predominantly the ortho position for 4-alkynyl-2,6-di-tert-butylphenols, the side chain for 4-alkenyl-2,6-di-tert-butylphenols, and the para position for 4-cyano- or 4-(1-methoxyimino)alkyl-2,6-di-tert-butylphenols as well as 2-alkynyl-, 2-alkenyl-, and 2-cyano-4,6-di-tert-butylphenols. The ortho tert-butylperoxylated products arise mainly from initially formed para tert-butylperoxylated products, by migration of the tert-butylperoxy group.
• Linked aryl aryloxypropanolamines as a new class of lipid catabolic agents
  作者：Michael T. Cox、Stuart E. Jaggers、Geraint Jones

  DOI：10.1021/jm00200a008

  日期：1978.2

  The synthesis of a series of stilbene, biaryl, tolane, diaryl ether, sulfide, sulfoxide, and sulfone oxypropanolamines as potential antiobesity agents is described. These compounds were evaluated in a mouse lipid catabolism screen, and the more active members of the series, 4, 57, and 58, were further investigated in rats and dogs. 1-(2,6-Ditert-butyl-4-trans-styrylphenoxy)-3-isopropylamino-2-propanol (4) possessed considerable lipid catabolic activity in mice and caused a significant reduction in the body weight of rats after 5 weeks and of dogs after 6 weeks. Only hematological irregularities in a chronic toxicity study precluded further development of this compound as an alternative antiobesity treatment.