1-heptyl-4-methoxybenzene | 92368-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-heptyl-4-methoxybenzene
• CAS: 92368-72-4
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: VNMDJTBBWZLPBU-UHFFFAOYSA-N

物化性质

• 熔点：
  5-6 °C
• 沸点：
  160-162 °C(Press: 17 Torr)
• 密度：
  0.873 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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-heptyl-4-methoxybenzene 在 lithium 、 乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以50%的产率得到4-庚基苯酚
  参考文献：
  名称：

  锂-乙二胺-THF-介导的芳烃α-位裂解的范围和局限性：在温和条件下芳基甲基醚和苄基醚的脱保护

  摘要：

  考察了锂-乙二胺-THF介导的芳烃α位还原键断裂的范围和局限性。即使在低至 -10 °C 的条件下，无氧 THF 中的锂金属（5 equiv）和乙二胺（7 equiv）等非常温和的条件对芳族醚的去甲基化也非常有效。烯丙基苄基醚也在这些条件下脱保护，烯丙醇部分几乎没有变化。通过这项研究，开发了 2,6-二甲基苄基 (m-xylylmethyl, MXM) 基团作为苄基的替代物，在上述还原条件下易于裂解。

  DOI：

  10.1055/s-2004-815977
• 作为产物：
  描述：

  2-(4-methoxyphenyl)octanal 在 5 mol% Pd/C 作用下， 以 环己烷 为溶剂， 反应 24.0h， 以95%的产率得到1-heptyl-4-methoxybenzene
  参考文献：
  名称：

  钯/碳催化脂肪醛脱羰的再评价

  摘要：

  描述了一种使用市售 Pd/C 催化剂对脂肪醛进行脱羰的改进方法。反应条件适用于线性、环状或空间要求高的底物，因为它们以高达 99% 的产率提供相应的烷烃。此外，这种 Pd/C 催化的方法表现出良好的官能团耐受性。先前报道的方法与当前方法的比较表明，反应条件对反应结果起着至关重要的作用。该方法还可用于合成工业上重要化合物的两步反应序列。

  DOI：

  10.1055/s-0037-1610433

文献信息

• <i>p</i>-Selective (sp²)-C–H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
  作者：Ganesh Pandey、Sandip Kumar Tiwari、Bhawana Singh、Kumar Vanka、Shailja Jain

  DOI：10.1039/c7cc07529d

  日期：——

  p-Selective (sp2)-C-H functionalization of electron rich arenes have been achieved for acylation and alkylation reaction, respectively, with acyl/alkylselenides by organic photoredox catalysis involving interesting mechanistic pathway.

  富电子芳烃的p-选择性（sp2）-CH功能化已通过涉及有趣机理的有机光氧化还原催化分别通过酰基/烷基硒化物进行酰化和烷基化反应。
• New One-pot Cross-coupling Reaction between Grignard Reagents and Alkoxymethyldiphenylphosphonium Iodides in situ-Formed from Alcohols, Chlorodiphenylphosphine and Iodomethane
  作者：Taichi Shintou、Wataru Kikuchi、Teruaki Mukaiyama

  DOI：10.1246/cl.2003.676

  日期：2003.8

  A new one-pot cross-coupling reaction between Grignard reagents and alkoxymethyldiphenylphosphonium iodides, which were in situ-formed from nBuLi-treated alcohols, chlorodiphenylphosphine and iodomethane, proceeded smoothly to afford the corresponding coupling products in good to high yields.

  格氏试剂与烷氧基甲基二苯基碘化鏻之间的新一锅交叉偶联反应由 nBuLi 处理的醇、氯代二苯基膦和碘甲烷原位形成，顺利进行，以良好到高产率提供相应的偶联产物。
• Nitrous Oxide-dependent Iron-catalyzed Coupling Reactions of Grignard Reagents
  作者：Peter Döhlert、Maik Weidauer、Stephan Enthaler

  DOI：10.2533/chimia.2015.327

  日期：——

  The formation of carbon–carbon bonds is one of the fundamental transformations in chemistry. In this regard the application of palladium-based catalysts has been extensively investigated during recent years, but nowadays research focuses on iron catalysis, due to sustainability, costs and toxicity issues; hence numerous examples for iron-catalyzed cross-coupling reactions have been established, based on the coupling of electrophiles (R1-X, X = halide) with nucleophiles (R2-MgX). Only a small number of protocols deals with the iron-catalyzed oxidative coupling of nucleophiles (R1-MgX + R2-MgX) with the aid of oxidants (1,2-dihaloethanes). However, some issues arise with these oxidants; hence more recently the potential of the industrial waste product nitrous oxide (N2O) was investigated, because the unproblematic side product N2 is formed. Based on that, we demonstrate the catalytic potential of easily accessible iron complexes in the oxidative coupling of Grignard reagents. Importantly, nitrous oxide was essential to obtain yields up to >99% at mild conditions (e.g. 1 atm, ambient temperature) and low catalyst loadings (0.1 mol%) Excellent catalyst performance is realized with turnover numbers of up to 1000 and turnover frequencies of up to 12000 h–1. Moreover, a good functional group tolerance is observed (e.g. amide, ester, nitrile, alkene, alkyne). Afterwards the reaction of different Grignard reagents revealed interesting results with respect to the selectivity of cross-coupling product formation.

  碳-碳键的形成是化学中的基本转化之一。在这方面，近年来广泛研究了钯基催化剂的应用，但如今研究重点转向铁催化，原因在于可持续性、成本和毒性问题；因此，已建立了许多铁催化的交叉偶联反应的示例，基于亲电子体（R1-X，X = 卤素）与亲核体（R2-MgX）的偶联。只有少数协议涉及铁催化的亲核体（R1-MgX + R2-MgX）的氧化偶联，借助氧化剂（1,2-二卤乙烷）。然而，这些氧化剂存在一些问题；因此，最近更多地研究了工业废物氧化亚氮（N2O）的潜力，因为无害的副产物N2会形成。基于这一点，我们展示了易于获得的铁配合物在氧化偶联格林纳德试剂中的催化潜力。重要的是，氧化亚氮对于在温和条件下（例如1大气压、室温）和低催化剂负载（0.1摩尔%）下获得高达>99%的产率至关重要。优秀的催化剂性能通过最高达1000的周转数和最高达12000 h-1的周转频率得以实现。此外，观察到了良好的官能团容忍性（例如酰胺、酯、腈、烯烃、炔烃）。随后，不同格林纳德试剂的反应揭示了与交叉偶联产物形成的选择性相关的有趣结果。
• Hydrogen‐Induced Formation of Surface Acid Sites on Pt/Al(PO₃)₃ Enables Remarkably Efficient Hydrogenolysis of C−O Bonds in Alcohols and Ethers
  作者：Kento Oshida、Kang Yuan、Yukari Yamazaki、Rio Tsukimura、Hidenori Nishio、Katsutoshi Nomoto、Hiroki Miura、Tetsuya Shishido、Xiongjie Jin、Kyoko Nozaki

  DOI：10.1002/anie.202403092

  日期：——

  nanoparticles have been developed for the hydrogenolysis of a wide range of alcohols and ethers under exceptionally mild conditions (0.1–1 atm of H2, as low as 70 °C). The key for the high performance of the catalyst is H2-induced formation of surface Brønsted acid sites, which efficiently activate C−O bonds in alcohols and ethers.

  偏磷酸铝负载的铂纳米颗粒已开发用于在极其温和的条件（0.1–1 atm H 2 ，低至 70 °C）下氢解各种醇和醚。该催化剂高性能的关键是H 2诱导表面布朗斯台德酸位点的形成，从而有效地激活醇和醚中的C−O键。
• Negishi Alkyl−Aryl Cross-Coupling Catalyzed by Rh: Efficiency of Novel Tripodal 3-Diphenylphosphino-2-(diphenylphosphino)methyl-2-methylpropyl Acetate Ligand
  作者：Syogo Ejiri、Shunsuke Odo、Hideki Takahashi、Yugo Nishimura、Kazuma Gotoh、Yasushi Nishihara、Kentaro Takagi

  DOI：10.1021/ol100210u

  日期：2010.4.16

  3-Diphenylphosphino-2-(diphenylphoshino)methyl-2-methylpropyl acetate acted as an efficient ligand for a Rh catalyst, achieving cross-coupling between arylzinc compounds bearing electron-withdrawing groups and alkyl electrophiles. The beneficial effect of the tripodal ligand and such aryl nucleophiles was discussed with regard to the specificity of the Rh catalysis.