2-(4-Methoxy-phenyl)-octan | 3307-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-Methoxy-phenyl)-octan
• 英文别名: 1-Methoxy-4-octan-2-ylbenzene
• CAS: 3307-20-8
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: DQGSMTJARVOICM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  2-(4-Methoxy-phenyl)-octan 在 碘代三甲硅烷 作用下， 反应 0.25h， 以100%的产率得到(1-甲基)庚基苯酚
  参考文献：
  名称：

  Methylation of Phenolic Hydroxyl Group and Demethylation of Anisoles

  摘要：

  在室温下，在双（三甲基硅）酰胺钠的存在下，酚羟基与碘甲烷发生了温和的甲基化反应。用纯净的碘三甲基硅烷进行微波加热，可以轻松实现反向反应，即甲基苯基醚的去甲基化反应。

  DOI：

  10.3184/030823409x431328
• 作为产物：
  描述：

  2-<4-Methoxyphenyl>-octan-2-ol 在 palladium on activated charcoal 盐酸 、 氢气 、 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 生成 2-(4-Methoxy-phenyl)-octan
  参考文献：
  名称：

  Sonawane,H.R. et al., Indian Journal of Chemistry, 1965, vol. 3, p. 260 - 265

  摘要：

  DOI：

文献信息

• Novel synthetic route to aryl alkanes from aromatic aldehydes and ketones. Novel geminal dialkylation of the carbonyl group of aromatic aldehydes and ketones
  作者：Alain Krief、M. Clarembeau、Ph. Barbeaux

  DOI：10.1039/c39860000457

  日期：——

  Benzyl-lithiums, readily available from benzyl methyl selenides and alkyl-lithiums, are efficiently alkylated; this reaction allows the geminal dialkylation of the carbonyl groups of aromatic aldehydes and ketones and the geminal aryl–alkylation of aliphatic analogues.

  可从苄基甲基硒化物和烷基锂容易获得的苄基锂被有效地烷基化。该反应可以使芳香族醛和酮的羰基发生双二烷基化反应，并使脂肪族类似物的双芳基烷基化反应。
• Iron-Catalyzed Oxidative Heterocoupling Between Aliphatic and Aromatic Organozinc Reagents: A Novel Pathway for Functionalized Aryl-Alkyl Cross-Coupling Reactions
  作者：Gérard Cahiez、Laura Foulgoc、Alban Moyeux

  DOI：10.1002/anie.200900175

  日期：——

  Aryl–alkyl cross‐coupling products are obtained by the iron‐catalyzed oxidative heterocoupling of organozinc reagents under mild conditions. This novel reaction pathway is versatile, allowing for the use of primary and secondary aliphatic diorganozinc reagents as coupling partners as well as tolerating functionalized aryl‐ and alkylzinc reagents.

  芳基-烷基交叉偶联产物是在温和条件下通过铁催化的有机锌试剂的氧化杂化获得的。这种新颖的反应途径用途广泛，可以使用脂族二有机锌一级和二级脂肪族试剂作为偶联伙伴，并可以耐受官能化的芳基锌和烷基锌试剂。
• Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C–N Bond Activation
  作者：Corey H. Basch、Jennie Liao、Jianyu Xu、Jacob J. Piane、Mary P. Watson

  DOI：10.1021/jacs.7b02389

  日期：2017.4.19

  strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki-Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C-N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be

  我们开发了一种通过 CN 键活化利用烷基胺作为烷化剂的策略。这种烷基吡啶盐的 Suzuki-Miyaura 交叉偶联很容易由伯胺形成，是金属催化交叉偶联的第一个例子，通过 CN 键活化胺与未活化的烷基。该反应具有广泛的范围和官能团耐受性。可以安装伯和仲烷基。初步研究表明 NiI/NiIII 催化循环。
• Nickel-catalyzed anti-Markovnikov hydroarylation of alkenes
  作者：Julia Nguyen、Andrea Chong、Gojko Lalic

  DOI：10.1039/c8sc05445b

  日期：——

  We have developed a nickel-catalyzed hydroarylation of alkenes using aryl halides as coupling partners. Excellent anti-Markovnikov selectivity is achieved with aryl-substituted alkenes and enol ethers. We also show that hydroarylation occurs with alkyl substituted alkenes to yield linear products. Preliminary examination of the reaction mechanism suggests irreversible hydrometallation as the selectivity

  我们开发了一种镍催化的烯烃加氢芳基化方法，使用芳基卤化物作为偶联伙伴。使用芳基取代的烯烃和烯醇醚可实现出色的抗马可夫尼科夫选择性。我们还表明，烷基取代的烯烃发生加氢芳基化，产生线性产物。反应机理的初步研究表明不可逆的加氢金属化是加氢芳基化的选择性决定步骤。
• Gallium dichloride-mediated reductive Friedel-Crafts reaction
  作者：Yukihiko Hashimoto、Kazuyuki Hirata、Hirotaka Kagoshima、Nobuhiro Kihara、Masaki Hasegawa、Kazuhiko Saigo

  DOI：10.1016/s0040-4020(01)87183-0

  日期：1993.7

  In the presence of gallium dichloride, the reaction of carbonyl compounds or their dimethylacetals with aromatic compounds afforded Friedel-Crafts alkylated adducts in good yields. It was suggested that the adducts were obtained by way of a reduction of the carbonyl compounds or their dimethylacetals, followed by the Friedel-Crafts reaction in one-pot. This is the first organic synthetic method with gallium dichloride, low valent gallium.