1-己基-4-甲氧基苯 | 81693-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-己基-4-甲氧基苯
• 英文名称: 1-hexyl-4-methoxybenzene
• 英文别名: 4-hexyl-anisole；4-Hexylanisole
• CAS: 81693-80-3
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: IAINKDPTJUTRFY-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C
• 沸点：
  124-125 °C(Press: 9 Torr)
• 密度：
  0.9276 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-己基-4-甲氧基苯 生成 1-甲氧基-4-正戊苯
  参考文献：
  名称：

  Skraup; Nieten, Chemische Berichte, 1924, vol. 57, p. 1303

  摘要：

  DOI：
• 作为产物：
  描述：

  1-己-1-炔基-4-甲氧基苯 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以95%的产率得到1-己基-4-甲氧基苯
  参考文献：
  名称：

  The Synthesis of Velloziolide via Nicholas Reaction Based γ-Carbonyl Cations

  摘要：

  The total synthesis of the 9,11-seco-rosane diterpene velloziolide (1) has been accomplished by employing the Nicholas reaction chemistry of 2a as a gamma-carbonyl cation equivalent. An initial model Study demonstrated the utility of Nicholas reactions of 2 in the generation of 4-arylalkynoate Co(2)(CO)(6) complexes, and in conjunction with Gilman cuprate addition and Johnson-Claisen rearrangement chemistry, the preparation of a 3-methyl-3-vinyl-4-arylalkanoate model for velloziolide. The Nicholas reaction/gamma-carbonyl cation methodology was then employed twice in the total synthesis to incorporate onto 3,4-methylenedioxytoluene the 4-carbon unit that became the gem-dimethyltetralin portion of the velloziolide and, subsequently, to incorporate the gamma-arylalkanoate function of the epsilon-lactone.

  DOI：

  10.1021/jo901471b

文献信息

• Thiol-Catalyzed Radical Decyanation of Aliphatic Nitriles with Sodium Borohydride
  作者：Takuji Kawamoto、Kyohei Oritani、Dennis P. Curran、Akio Kamimura

  DOI：10.1021/acs.orglett.8b00626

  日期：2018.4.6

  Radical decyanation of aliphatic nitriles was achieved in the presence of NaBH4 and a thiol. The reaction proceeds via a radical mechanism involving borane radical anion addition to nitrile to form an iminyl radical, which undergoes carbon–carbon cleavage. Reductive radical addition to acrylonitrile is followed by decyanation to give a two-carbon homologated product in a net radical ethylation reaction

  在NaBH 4和硫醇的存在下，脂族腈的自由基发生了脱氰。反应是通过自由基机理进行的，该机理涉及将硼烷自由基阴离子加到腈上形成亚氨基自由基，然后进行碳-碳裂解。向丙烯腈中还原性自由基加成后，进行脱氰，在净自由基乙基化反应中得到两碳均聚物。
• Visible-Light-Induced Nickel-Catalyzed Cross-Coupling with Alkylzirconocenes from Unactivated Alkenes
  作者：Yadong Gao、Chao Yang、Songlin Bai、Xiaolei Liu、Qingcui Wu、Jing Wang、Chao Jiang、Xiangbing Qi

  DOI：10.1016/j.chempr.2019.12.010

  日期：2020.3

  Transition-metal-catalyzed cross-coupling reactions between naturally abundant sp3-hybridized carbon centers facilitate access to diverse molecules with complex three-dimensional structures. Organometallic compounds are among one of the most powerful reagents that are broadly used in carbon–carbon bond formations. Although sp2-hybridized organometallic compounds are widely employed in cross-couplings, sp3-hybridized

  自然丰富的sp 3-杂化碳中心之间的过渡金属催化交叉偶联反应有助于获得具有复杂三维结构的各种分子。有机金属化合物是最强大的试剂之一，广泛用于碳-碳键的形成。尽管sp 2-杂化的有机金属化合物广泛用于交叉偶联，但是sp 3-杂化的有机金属偶联剂的开发较少。在这里，我们报告可见光诱导的单个镍催化的C（sp 3）–C（sp 3），C（sp 3）–C（sp 2）和C（sp 3）–C（sp）使用烷基锆茂的交叉偶联反应，该反应很容易从末端或内部未活化的烯烃通过加氢锆和链步反应就地生成。该方法温和，适用于多种底物，包括伯，仲，叔烷基，芳基，烯基，炔基卤化物和各种烯烃。机理研究表明，镍催化的自由基交叉偶联是一种新颖的途径，代表了锆锆茂的首次可见光诱导的转变。
• Hydrodecyanation of Secondary Alkyl Nitriles and Malononitriles to Alkanes using DiMeImd-BH₃
  作者：Takuji Kawamoto、Kyohei Oritani、Atsushi Kawabata、Tsubasa Morioka、Hiroshi Matsubara、Akio Kamimura

  DOI：10.1021/acs.joc.0c00105

  日期：2020.5.1

  The decyanation of secondary aliphatic nitriles and the 2-fold decyanation of malononitriles leading to alkanes in the presence of 1,3-dimethylimidazol-2-ylidene borane (diMeImd-BH3) are reported. These reactions proceed via a radical mechanism that involves the addition of a borane radical to the nitrile to form an iminyl radical, followed by cleavage of a carbon-carbon bond. Theoretical calculations

  据报道，在1，3-二甲基咪唑-2-亚烷基硼烷（diMeImd-BH3）存在下，仲脂肪族腈的脱氰作用和丙二腈的2倍脱氰作用生成烷烃。这些反应通过自由基机理进行，该自由基机理包括向腈中加入硼烷自由基以形成亚氨基自由基，然后裂解碳-碳键。理论计算表明，这些亚胺基的β-裂解是该反应中决定速率的步骤，该裂解提供了NHC-BH2CN和相应的烷基。
• Ligands for metals and improved metal-catalyzed processes based thereon
  申请人：Massachusetts Institute of Technology

  公开号：US06307087B1

  公开（公告）日：2001-10-23

  One aspect of the present invention relates to novel ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.

  本发明的一个方面涉及用于过渡金属的新颖配体。本发明的第二个方面涉及在过渡金属催化的碳-杂原子和碳-碳键形成反应中使用含有这些配体的催化剂。本方法在许多过渡金属催化反应的特征上提供了改进，包括适宜的底物范围、反应条件和效率。
• Terminal‐Selective Functionalization of Alkyl Chains by Regioconvergent Cross‐Coupling
  作者：Stéphanie Dupuy、Ke‐Feng Zhang、Anne‐Sophie Goutierre、Olivier Baudoin

  DOI：10.1002/anie.201608535

  日期：2016.11.14

  zinc bromides and regioconvergent Negishi coupling with aryl or alkenyl triflates. The use of a suitable phosphine ligand favoring Pd migration enabled the selective formation of the linear cross‐coupling product. Subsequently, mixtures of secondary alkyl bromides were prepared from linear alkanes by standard bromination, and regioconvergent cross‐coupling then provided access to the corresponding linear

  碳氢化合物仍然是功能化有机分子的最重要前体，在新型CH键功能化方法的发现中引起了人们的兴趣。我们在这里描述了一种新的步骤经济的方法，该方法使C-C键能够在直链烷烃的末端位置进行构建。首先，我们表明仲烷基溴化物可以原位转化为烷基溴化锌和与会聚芳基或烯基三氟甲磺酸酯的区域收敛的Negishi。使用合适的膦配体促进Pd迁移，可以选择性形成线性交叉偶联产物。随后，通过标准溴化反应，由直链烷烃制备仲烷基溴化物的混合物，然后通过区域会聚交叉偶联，仅需两个步骤即可获得相应的线性芳基化产物。