1-(2-methoxy-2-phenylethyl)-4-nitrobenzene | 106111-26-6

• 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: 1-(2-methoxy-2-phenylethyl)-4-nitrobenzene
• 英文别名: 1-methoxy-2-(p-nitrophenyl)-1-phenylethane；1-nitro-4-(2-methoxy-2-phenylethyl)benzene；1-Methoxy-2-p-nitrophenyl-1-phenylethan
• CAS: 106111-26-6
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: GBDHCPARITZTJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对硝基苯乙酸 在 sodium tetrahydroborate 、 三氯化铝 、 氯化亚砜 、 sodium 作用下， 以 甲醇 为溶剂， 反应 3.08h， 生成 1-(2-methoxy-2-phenylethyl)-4-nitrobenzene
  参考文献：
  名称：

  硝基苄基衍生物的光-逆-羟醛型反应的结构和机理。碳-碳键的光化学异裂裂解

  摘要：

  光解 d'aryl-2 propanols-1 en phase aqueuse et en phase oxygenee; 分别获得甲苯、双苄和氢过氧苯。光逆醛醇化的机械练习曲

  DOI：

  10.1021/ja00221a038

文献信息

• Oxyarylation and Aminoarylation of Styrenes Using Photoredox Catalysis
  作者：Gabriele Fumagalli、Scott Boyd、Michael F. Greaney

  DOI：10.1021/ol401940c

  日期：2013.9.6

  A three-component coupling of styrenes is reported, using photoredox catalysis to achieve simultaneous arylation and C–O or C–N bond formation across the styrene double bond.

  据报道，通过光氧化还原催化，苯乙烯可以实现三组分偶联，同时实现芳基化和跨苯乙烯双键的C–O或C–N键的形成。
• Olefin Bifunctionalization: A Visible-light Photoredox-catalyzed Aryl Alkoxylation of Olefins
  作者：Eiji Yamaguchi、Wakako Tanaka、Akichika Itoh

  DOI：10.1002/asia.201801211

  日期：2019.1.4

  Olefin bifunctionalization is a facile route to obtain complex molecules from abundant and commercially available olefin feedstocks. Visible light together with a catalytic amount of tris(bipyridine)ruthenium salt catalyzes the aryl alkoxylation of styrenes with aryl diazonium salts in alcohol solvents via a photoredox process. The scope of this proposed reaction with respect to various aryl diazonium

  烯烃双官能化是从丰富的和可商购的烯烃原料中获得复杂分子的简便途径。可见光与催化量的三（联吡啶）钌盐一起通过光氧化还原工艺在醇溶剂中催化苯乙烯与芳基重氮盐的芳基烷氧基化反应。已经针对各种芳基重氮盐和苯乙烯研究了该拟议反应的范围。
• Photoredox-Catalyzed Intermolecular Radical Arylthiocyanation/Arylselenocyanation of Alkenes: Access to Aryl-Substituted Alkylthiocyanates/Alkylselenocyanates
  作者：Injamam Ul Hoque、Soumyadeep Roy Chowdhury、Soumitra Maity

  DOI：10.1021/acs.joc.8b03155

  日期：2019.3.15

  An efficient and highly selective approach for intermolecular arylthiocyanation/arylselenocyanation of alkenes has been reported under mild conditions. Using diazonium salts as the arylating agent and ammonium thiocyanate as the thiocyanate source, chemoselective difunctionalization of alkenes has been done under irradiation of visible light. Both styrenes and acrylates work well to deliver various aryl-substituted alkylthiocyanates in good to excellent yields. In addition, hitherto unknown beta-aryl alkylselenocyanates were also synthesized using the developed protocol with potassium selenocyanate.
• Electrophilic Substitution at Saturated Carbon. XXVIII. The Stereochemical Capabilities of Vinyl Anions¹
  作者：D. H. Hunter、Donald J. Cram

  DOI：10.1021/ja00976a018

  日期：1966.12
• Transition-Metal-Free Catalytic Carboalkoxylation of Styrenes at Room Temperature
  作者：R. Govindarajan、Jasimuddin Ahmed、Asim Kumar Swain、Swadhin K. Mandal

  DOI：10.1021/acs.joc.9b01744

  日期：2019.11.1

  Herein, we describe the first transition-metal-free catalytic carboalkoxylation of styrenes with aryl diazonium salts by Meerwein addition in the presence of a phenalenyl ligand at room temperature without requiring any light stimulation. This three-component reaction allows facile difunctionalization of styrene derivatives with various alcohols (such as 1, 2, and 3 degrees) as the source of alkoxy group during this transformation. The key intermediates and the transition states involved in this reaction path were unraveled by a series of control experiments coupled with density functional theory calculations. The full mechanistic investigation provides an understanding of the selectivity toward carboalkoxylation Meerwein arylation addition elimination) in the presence of various alcohols over the simple arylation to multiple bond (Meerwein arylation-elimination) reaction.