1-(4-Methoxyphenyl)-2-methoxypropane | 65725-89-5

• 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: 1-(4-Methoxyphenyl)-2-methoxypropane
• 英文别名: 1-methoxy-4-(2-methoxypropyl)benzene；4-(2-Methoxypropyl)anisole
• CAS: 65725-89-5
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: YHQFKQWLXKHBRM-UHFFFAOYSA-N

物化性质

• 沸点：
  236.8±15.0 °C(Predicted)
• 密度：
  0.969±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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Methoxyphenyl)-2-methoxypropane 以 水 为溶剂， 生成
  参考文献：
  名称：

  水溶液中 2-、3- 和 4-芳基烷醇自由基阳离子侧链断裂中的氧与碳酸度：OH 基团与芳环之间距离的影响1

  摘要：

  已通过脉冲辐解对水中 2-、3- 和 4-(4-甲氧基苯基) 烷醇自由基阳离子的衰变进行动力学研究，反应产物由稳态 γ-辐解实验或钾促进的反应确定12-钨钴（III）酸盐，一种真正的单电子氧化剂。发现所有 2-芳基烷醇自由基阳离子以扩散控制的速率与 -OH 反应，导致 Cα-Cβ 键断裂产物。这表明由醇 OH 基团的去质子化引起的反应。在酸性介质（pH = 4）中，这些自由基阳离子的衰变率要低得多，导致 Cα-H 去质子化（对于 2-（4-甲氧基苯基）乙醇 (1•+) 和 1-(4-甲氧基苯基)-2-丙醇 (4•+)）或 Cα-Cβ 键裂解产物（对于 1-苯基-2-（4-甲氧基苯基）乙醇 (5•+) 和 2-甲基-1-苯基-3-(4-甲氧基苯基)-2-丙醇 (6•+) ))。3-(4-甲氧基苯基)丙醇自由基阳离子 (2•+) 在酸性介质 (pH = 4) 中以接近 1•+ 的速率反应，发生

  DOI：

  10.1021/ja990352+
• 作为产物：
  描述：

  茴香烯 在 2-苯基丙二腈 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 96.0h， 以84%的产率得到1-(4-Methoxyphenyl)-2-methoxypropane
  参考文献：
  名称：

  Direct Catalytic Anti-Markovnikov Hydroetherification of Alkenols

  摘要：

  A direct intramolecular anti-Markovnikov hydroetherification reaction of alkenols is described. By employing Catalytic quantities of commercially available 9-mesityl-10-methylacridinium perchlorate and 2-phenyl-malononitrile as a redox-cycling source of a H-atom, we report the anti-Markovnikov hydroetherification of alkenes with complete regioselectivity, In addition, we present results demonstrating that this novel catalytic system can be applied to the anti-Markovnikov hydrolactonization of alkenoic acids.

  DOI：

  10.1021/ja309635w

文献信息

• Novel Oxidative Ugi Reaction for the Synthesis of Highly Active, Visible-Light, Imide-Acridinium Organophotocatalysts
  作者：Andrea Gini、Mustafa Uygur、Thomas Rigotti、José Alemán、Olga García Mancheño

  DOI：10.1002/chem.201802830

  日期：2018.8.27

  A newly designed class of acridinium‐based organophotocatalysts bearing an imide group at the C9‐position is presented. To achieve these unprecedented structures, a synthetic strategy based on a novel straightforward oxidative Ugi‐type reaction at the benzylic position of C9‐unsubstituted acridanes was developed. The introduction of the imide‐unit affords a notable photocatalytic activity enhancement

  提出了一种新设计的基于a啶基的有机光催化剂，该催化剂在C9位带有一个酰亚胺基团。为了实现这些空前的结构，开发了一种基于新的直接氧化的Ugi型反应的合成策略，该反应在C9未取代的cri啶酮的苄基位置上进行。酰亚胺单元的引入显着增强了光催化活性，从而可以在不同的氧化性和还原性可见光催化反应中进行有效转化。
• Addition reaction of 2-phenylbenzoic acid onto unactivated olefins catalyzed by Ru(II)–xantphos catalysis
  作者：Yohei Oe、Tetsuo Ohta、Yoshihiko Ito

  DOI：10.1016/j.tetlet.2010.03.052

  日期：2010.5

  Ru(II)–xantphos catalysis is found to be effective for the addition reaction of 2-phenylbenzoic acid onto unactivated olefins. Thus, the reactions of 2-phenylbenzoic acid and unactivated olefins are carried out in the presence of 5 mol % of Ru(II)–xantphos catalysis in refluxing CHCl3 for 48 h to afford the corresponding esters in 40–95% yield. The control experiments indicate that the influence of

  发现Ru（II）–xantphos催化对于将2-苯基苯甲酸加成到未活化的烯烃上是有效的。因此，2-苯基苯甲酸和未活化的烯烃的反应是在5 mol％的Ru（II）-黄药催化下，在回流的CHCl 3中进行48小时，以40-95％的收率得到相应的酯。对照实验表明，在我们的新催化体系中，TfOH对布朗斯台德酸催化剂的影响很小。
• Probing the Free Energy Landscape of Organophotoredox-Catalyzed Anti-Markovnikov Hydrofunctionalization of Alkenes
  作者：Sharath Chandra Mallojjala、Victor O. Nyagilo、Stephanie A. Corio、Alafate Adili、Anuradha Dagar、Kimberly A. Loyer、Daniel Seidel、Jennifer S. Hirschi

  DOI：10.1021/jacs.2c07807

  日期：2022.9.28

  anti-Markovnikov alkene hydrofunctionalization reactions─hydroesterification, hydroamination, and hydroetherification─enabled by organophotoredox catalysis. All three reactions are found to proceed via initial oxidation of the model alkenes to form a radical cation intermediate, followed by sequential nucleophilic attack and hydrogen-atom transfer to deliver the hydrofunctionalized product. A normal

  实验性13 C 动力学同位素效应 (KIE) 为有机光氧化还原催化实现的三种分子间反马尔可夫尼科夫烯烃加氢官能化反应——加氢酯化、加氢胺化和加氢醚化提供了前所未有的机理洞察力。发现所有三个反应都是通过模型烯烃的初始氧化形成自由基阳离子中间体，然后进行连续的亲核攻击和氢原子转移以提供加氢官能化产物。经历亲核攻击的烯烃碳上的正常13 C KIE 为所有三个反应中的限速亲核攻击提供了定性证据。与预测13的比较从该步骤的密度泛函理论 (DFT) 计算获得的 C KIE 值表明，烯烃氧化在加氢酯化和加氢胺化中具有部分限速影响，而亲核攻击仅在加氢醚化反应中限速。碱性添加剂（2,6-二甲基吡啶）通过去质子化激活亲核试剂，并且是对自由基阳离子进行亲核攻击的过渡态的组成部分，为开发这些反应的不对称版本提供了重要的设计原则。更富电子的吡啶碱基（2,6-二甲氧基吡啶）在分子间和分子内氢化反应中表现出相当大的速率增强。
• Lee, Ikchoon; Lee, Won Heui; Lee, Hai Whang, Journal of the Chemical Society. Perkin transactions II, 1991, # 5, p. 785 - 791
  作者：Lee, Ikchoon、Lee, Won Heui、Lee, Hai Whang、Lee, Byung Choon

  DOI：——

  日期：——
• Structural Effects in the TiO2-Photocatalyzed Oxidation of Alkylaromatic Compounds in Acetonitrile in the Presence of Ag2SO4
  作者：Enrico Baciocchi、Cesare Rol、Giovanni V. Sebastiani、Luca Taglieri

  DOI：10.1021/jo00097a031

  日期：1994.9

  The TiO2-sensitized photochemical reactions of some alkylbenzenes (ArCH(2)R; R = H, Me), 1-aryl-2-propanols, and corresponding methyl ethers (ArCH2C(OR'')R'CH3; R', R'' = H, Me) have been investigated in MeCN, in the presence of Ag2SO4, which traps the photogenerated electrons. With ArCH(2)R, the corresponding radical cations are generated by the photoexcited TiO2 and are then deprotonated to form benzyl radicals; from the latter 1,2-diarylethanes, 3-arylpropanonitriles, and benzylacetamides are obtained as major products. With ArCH2C(OR'')R'CH3, the formed radical cations undergo C-C bond cleavage as the only observed route, when Ar = Ph. However, when Ar = 4-MeOPh and R' = H, the radical cation undergoes C-H bond cleavage as the major or exclusive reaction path. These results are compared with those obtained in the corresponding homogeneous photochemical reactions, and their implications with respect to the role of the structure on the side-chain reactivity of aromatic radical cations are discussed.