1-methoxy-4-(1-phenylbutyl)benzene | 1438827-73-6

• 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-methoxy-4-(1-phenylbutyl)benzene
• 英文别名: 1-Methoxy-4-(1-phenylbutyl)benzene
• CAS: 1438827-73-6
• 化学式: C₁₇H₂₀O
• 分子量: 240.345
• InChiKey: VHLARQBLBXOJKV-UHFFFAOYSA-N

物化性质

• 沸点：
  342.8±21.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  dimethyl-[2-[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl]phenyl]silane 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三甲基氯硅烷 、 水 、 potassium carbonate 、 三苯基膦 、 potassium iodide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 26.0h， 生成 1-methoxy-4-(1-phenylbutyl)benzene
  参考文献：
  名称：

  Iridium-Catalyzed Borylation of Secondary Benzylic C–H Bonds Directed by a Hydrosilane

  摘要：

  Most functionalizations of C-H bonds by main-group reagents occur at aryl or methyl groups. We describe a highly regioselective borylation of secondary benzylic C-H bonds catalyzed by an iridium precursor and 3,4,7,8-tetramethyl-1,10-phenanthroline as the ligand. The reaction is directed to the benzylic position by a hydrosilyl substituent. This hydrosilyl directing group is readily deprotected or transformed to other functional groups after the borylation reaction, providing access to a diverse set of secondary benzylboronate esters by C-H borylation chemistry.

  DOI：

  10.1021/ja403462b

文献信息

• Nickel‐Catalyzed Chain‐Walking Cross‐Electrophile Coupling of Alkyl and Aryl Halides and Olefin Hydroarylation Enabled by Electrochemical Reduction
  作者：Gadde Sathish Kumar、Anatoly Peshkov、Aleksandra Brzozowska、Pavlo Nikolaienko、Chen Zhu、Magnus Rueping

  DOI：10.1002/anie.201915418

  日期：2020.4.16

  novel route to afford 1,1-diarylalkane derivatives from simple and readily available alkyl and aryl halides in good yields and excellent regioselectivities under mild conditions. The procedure shows good tolerance for a broad variety of functional groups and both primary and secondary alkyl halides can be used. Furthermore, the reaction was successfully scaled up to the multigram scale proving the

  开发了第一种用于镍催化的交叉亲电子偶联的电化学方法。该方法提供了一种新颖的途径，可以在温和的条件下，以简单的，容易获得的烷基和芳基卤化物以良好的收率和优异的区域选择性来制备1,1-二芳基烷烃衍生物。该方法显示出对多种官能团的良好耐受性，并且可以使用伯烷基卤和仲烷基卤。此外，该反应已成功扩大到数克规模，证明了其在工业应用中的潜力。机理研究表明，在电还原链走芳基化反应中形成了氢化镍，这导致了新的苯乙烯催化的镍催化加氢芳基化反应的进一步发展，提供了一系列1，
• BH ₃  ⋅ Me ₂ S: An Alternative Hydride Source for NiH‐Catalyzed Reductive Migratory Hydroarylation and Hydroalkenylation of Alkenes
  作者：Jiandong Liu、Hegui Gong、Shaolin Zhu

  DOI：10.1002/ejoc.202100005

  日期：2021.3.12

  The inexpensive borane dimethylsulfide (BMS) complex was found to be an efficient hydride source for nickel‐hydride catalyzed migratory hydrofunctionalization. Using BMS, migratory hydroarylation and migratory hydroalkenylation were achieved with broad substrate scope under mild conditions.

  廉价的硼烷二甲基硫醚（BMS）络合物被发现是氢化镍催化迁移性加氢官能化的有效氢化物来源。使用BMS，在温和条件下，在较宽的底物范围内实现了迁移加氢芳基化和迁移加氢烯基化。
• Ligand‐Enabled Nickel‐Catalyzed Redox‐Relay Migratory Hydroarylation of Alkenes with Arylborons
  作者：Yuli He、Chuang Liu、Lei Yu、Shaolin Zhu

  DOI：10.1002/anie.202001742

  日期：2020.6.2

  A redox-relay migratory hydroarylation of isomeric mixtures of olefins with arylboronic acids catalyzed by nickel complexes bearing diamine ligands is described. A range of structurally diverse 1,1-diarylalkanes, including those containing a 1,1-diarylated quaternary carbon, were obtained in excellent yields and with high regioselectivity. Preliminary experimental evidence supports the proposed non-dissociated

  描述了由带有二胺配体的镍配合物催化的烯烃与芳基硼酸的异构体混合物的氧化还原-中继迁移氢化芳基化。以优异的产率和高区域选择性获得了一系列结构多样的1，1-二芳基烷烃，包括那些含有1，1-二芳基化季碳的烷烃。初步的实验证据支持了在苄基位置进行选择性还原消除之前，芳烃-镍（II）-氢化物物种沿着烯烃的烷基链的非离解链走动。证明低至0.5mol％的催化剂负载量对于大规模合成是足够的，同时保持高反应性，突出了该转化的实用价值。
• Nickel‐Catalyzed Electrochemical Reductive Relay Cross‐Coupling of Alkyl Halides to Aryl Halides
  作者：Ke‐Jin Jiao、Dong Liu、Hong‐Xing Ma、Hui Qiu、Ping Fang、Tian‐Sheng Mei

  DOI：10.1002/anie.201912753

  日期：2020.4.16

  A highly regioselective Ni-catalyzed electrochemical reductive relay cross-coupling between an aryl halide and an alkyl halide has been developed in an undivided cell. Various functional groups are tolerated under these mild reaction conditions, which provides an alternative approach for the synthesis of 1,1-diarylalkanes.

  在未分开的电池中已经开发出芳基卤化物和烷基卤化物之间的高度区域选择性的镍催化的电化学还原中继交叉偶联。在这些温和的反应条件下可以耐受各种官能团，这为合成1,1-二芳基烷烃提供了另一种方法。
• Remote Migratory Cross-Electrophile Coupling and Olefin Hydroarylation Reactions Enabled by in Situ Generation of NiH
  作者：Fenglin Chen、Ke Chen、Yao Zhang、Yuli He、Yi-Ming Wang、Shaolin Zhu

  DOI：10.1021/jacs.7b08064

  日期：2017.10.4

  ligand-controlled nickel migration/arylation. This general protocol allows the use of abundant and bench-stable alkyl bromides and aryl bromides for the synthesis of a wide range of structurally diverse 1,1-diarylalkanes in excellent yields and high regioselectivities under mild conditions. We also demonstrated that alkyl bromide could be replaced by the proposed olefin intermediate while using n-propyl bromide/Mn0

  通过配体控制的镍迁移/芳构化，已经开发出一种用于远程还原性交亲电试剂偶联的高效策略。该通用方案允许使用大量稳定的烷基溴化物和芳基溴化物，在温和条件下以优异的收率和高区域选择性合成各种结构多样的1,1-二芳基烷烃。我们还证明，在使用正丙基溴/ Mn 0作为潜在的氢化物源的同时，烷基溴可以被提议的烯烃中间体替代。