α-ethenyl-α-phenyl-4-methoxybenzenemethanol | 101018-39-7

• 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: α-ethenyl-α-phenyl-4-methoxybenzenemethanol
• 英文别名: 1-(4-methoxyphenyl)-1-phenylprop-2-en-1-ol；1-phenyl-1-(p-methoxyphenyl)allyl alcohol；1-(4-methoxyphenyl)-1-phenyl-2-propenol；1-phenyl-1-(4-methoxyphenyl)-2-propen-1-ol
• CAS: 101018-39-7
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: NEUJNTCVEITLII-UHFFFAOYSA-N

物化性质

• 沸点：
  393.3±30.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-ethenyl-α-phenyl-4-methoxybenzenemethanol 在 ferric(III) bromide 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.5h， 生成 (Z)-1-(2,4-dinitrophenyl)-2-(2-(4-methoxyphenyl)-1-phenyl-3-(phenylselanyl)propylidene)hydrazine
  参考文献：
  名称：

  铁通过苯基硒基化/ 1,2-芳基迁移促进烯烃的双官能化

  摘要：

  铁，α，α-二芳基和α-芳基-α-烷基烯丙基醇的双官能化已在温和的条件下通过N-（苯基硒代）邻苯二甲酰亚胺（N-PSP）有效地实现了。将原位生成的苯基硒阳离子（PhSe +）添加到烯烃的C═C键上，以一种与众所周知的自由基途径相反的迁移偏好，伴随着1,2-芳基迁移，引发区域选择性的苯基硒基化反应。所得到的烯烃双官能化产物，即α-芳基-β-苯基硒烯酮的氢解，以及随后的铜催化的脱氢硒烯化有效地提供了官能化的2-吡唑啉衍生物。

  DOI：

  10.1021/acs.orglett.7b02751
• 作为产物：
  描述：

  苯基溴化镁 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 α-ethenyl-α-phenyl-4-methoxybenzenemethanol
  参考文献：
  名称：

  UV Light-Mediated Difunctionalization of Alkenes through Aroyl Radical Addition/1,4-/1,2-Aryl Shift Cascade Reactions

  摘要：

  UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.

  DOI：

  10.1021/acs.orglett.5b00144

文献信息

• Silver-catalyzed carbonphosphonation of α,α-diaryl allylic alcohols: synthesis of β-aryl-γ-ketophosphonates
  作者：Xia Mi、Chenyang Wang、Mengmeng Huang、Yusheng Wu、Yangjie Wu

  DOI：10.1039/c4ob01739k

  日期：——

  Silver-catalyzed carbonphosphonation of α,α-diaryl allylic alcohols is achieved. A series of γ-ketophosphonates with different substituents were readily obtained. The mechanistic study indicated that the reaction was initiated by the addition of P-radicals, which sequentially undergo 1,2-migration of an aryl group to form C(Ar)–C(sp3) bonds.

  银催化的α,α-二芳基烯丙醇的碳膦化反应得以实现。一系列含有不同取代基的γ-酮膦酸酯被轻易地合成出来。机理研究表明，该反应始于P-自由基的加成，随后通过芳基的1,2-迁移形成C(Ar)–C(sp3)键。
• Electrochemical Oxidative Aryl(alkyl)trifluoromethylation of Allyl Alcohols via 1,2-Migration
  作者：Zhipeng Guan、Huamin Wang、Yange Huang、Yunkun Wang、Shengchun Wang、Aiwen Lei

  DOI：10.1021/acs.orglett.9b01518

  日期：2019.6.21

  An electrochemical oxidative difunctionalization of allyl alcohols for the synthesis of β-trifluoromethyl ketones is achieved through a 1,2-migration process. A series of β-trifluoromethyl ketones can be facilely obtained utilizing CF3SO2Na as a radical source, eliminating the use of metals and sacrificial chemical oxidants. Importantly, this protocol not only realizes aryl migration but also offers

  通过1，2-迁移过程可实现烯丙醇的电化学氧化双官能化，以合成β-三氟甲基酮。利用CF 3 SO 2 Na作为自由基源可以轻松获得一系列β-三氟甲基酮，而无需使用金属和牺牲性化学氧化剂。重要的是，该协议不仅实现了芳基迁移，而且还提供了烷基迁移产物。另外，电化学催化的环膨胀和克级反应证明了该方案的合成有用性。
• Divergent Synthesis of Trifluoromethyl Sulfoxides and β-SCF₃ Carbonyl Compounds by Tandem Trifluoromethylthiolation/Rearrangement of Allylic and Propargylic Alcohols
  作者：Deng Zhu、Tong-Mei Ding、Hui-Yun Luo、Hua Ke、Zhi-Min Chen

  DOI：10.1021/acs.orglett.0c02875

  日期：2020.10.2

  A selenium-catalyzed trifluoromethylthiolation/[2,3]-sigmatropic rearrangement of tertiary allylic and propargylic alcohols which could provide straightforward and facile access to trifluoromethyl sulfoxides was developed. Various allylic and allenic trifluoromethyl sulfoxides were obtained with moderate to excellent yields. Meanwhile, a Lewis acid mediated trifluoromethylthiolation/1,2-rearrangement

  开发了硒催化的三烯丙基和丙炔醇的三氟甲基硫醇化/ [2,3]-σ重排，可提供直接而又容易获得的三氟甲基亚砜。获得各种烯丙基和烯丙基三氟甲基亚砜，具有中等至优异的产率。同时，路易斯酸介导的trifluoromethylthiolation / 1,2-重排合成β-SCF 3的羰基化合物也已实现。这两个串联反应的特征是反应条件温和且不含金属。在这两个反应中，揭示了亲电三氟甲基硫醇化的化学选择性。
• Selenium-Catalyzed Trifluoromethylsulfinylation/Rearrangement of Allylic and Propargylic Alcohols: Access to Allylic and Allenic Triflones
  作者：Deng Zhu、Hui-Yun Luo、Zhi-Min Chen

  DOI：10.1021/acs.orglett.0c04236

  日期：2021.2.5

  A selenium-catalyzed trifluoromethylsulfinylation/rearrangement of allylic and propargylic alcohols for synthesizing triflones was developed for the first time. Various allylic and allenic triflones were delivered in moderate to excellent yields. After numerous control experiments were performed, it was suggested that this transformation includes an unusual [+SCF3] group disproportionation process

  首次开发了硒催化的三氟甲基亚磺酰基化/烯丙基和炔丙基醇的重排反应，用于合成三氟甲磺酸。各种烯丙基和艾伦三烯酮以中等至优异的产率递送。经过大量的控制实验后，有人认为这种转变包括一个不寻常的[ + SCF 3 ]基歧化过程，该过程形成了硒原位催化的[ + SOCF 3 ]，H 2 O被用作氧资源。该反应具有温和的反应条件和良好的底物相容性，并且不含过渡金属。
• Photo-induced phosphorus radical involved semipinacol rearrangement reaction: Highly synthesis of γ-oxo-phosphonates
  作者：Chunhai Wang、Xiaoling Huang、Xueting Liu、Suqian Gao、Bin Zhao、Shangdong Yang

  DOI：10.1016/j.cclet.2019.08.011

  日期：2020.3

  the unique biological activities, and they have some attractive prospects as clinical drug moleculars. Herein, a new approach for the synthesis of γ-oxo-phosphonates (the precursor of hydroxyphosphoric acid) has been established through the semipinacol rearrangement tactic involved the photo-induced phosphorus radical process. Most important, this transformation is avoid of the external oxidants, and

  摘要羟基磷酸具有独特的生物活性，作为临床药物分子具有广阔的应用前景。在此，通过涉及光诱导的磷自由基过程的半频哪醇重排策略，已经建立了用于合成γ-氧代膦酸酯（羟基磷酸的前体）的新方法。最重要的是，这种转变避免了外部氧化剂，并且在日光照射下非常好地发生，同时γ-氧代膦酸酯很容易衍生得到γ-羟基磷酸，从而突出了该方法的合成价值。