1-甲氧基-4-(1-甲氧基丙基)苯 | 88932-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-甲氧基-4-(1-甲氧基丙基)苯
• 英文名称: 1-methoxy-4-(1-methoxypropyl)benzene
• 英文别名: 1-(4-methoxyphenyl)-1-methoxypropane
• CAS: 88932-42-7
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: LRPQHVAGARYGFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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-甲氧基-4-(1-甲氧基丙基)苯 在 Wilkinson's catalyst 碘代三甲硅烷 、 氢气 、 四氯化钛 作用下， 以 苯 为溶剂， 反应 25.0h， 生成 (3R*,4S*)-3-(2-Nitro-4-methoxyphenyl)-4-(hydroxyphenyl)hexane
  参考文献：
  名称：

  Silicon-mediated synthesis of bibenzyl systems: synthesis of ring and side-chain functionalized hexestrol derivatives

  摘要：

  DOI：

  10.1021/jo00181a021
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 titanium(IV) isopropylate 、 (R)-1,1'-Bi-2-naphthol 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 14.5h， 生成 1-甲氧基-4-(1-甲氧基丙基)苯
  参考文献：
  名称：

  Efficient assembly of α-aryl and α-vinyl nitriles via iron-catalyzed ether bond activation

  摘要：

  A novel and practical method for the synthesis of diverse alpha-aryl and alpha-vinyl nitriles was developed via an iron-catalyzed sp(3) C-O ether bond cleavage with C-C bond formation in the reaction of pi-activated ethers with TMSCN. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.083

文献信息

• Controlling factors determining the regiochemistry of intramolecular alkoxymercuration
  作者：Yasuhisa Senda、Hiroko Kanto、Hiroki Itoh

  DOI：10.1039/a608003k

  日期：——

  The intramolecular alkoxymercuration of (E)-5-arylpent-4-en-1-ols indicated that the regioselectivity is closely related to the Hammett constants of the para-substituents on the benzene ring. Large solvent effects on the regioselectivity were also observed. These results were compared with those of the methoxymercuration of β-methylstyrene analogues. The regioselectivity is discussed in terms of steric effects as well as the electronic effects which are suggested by the MO calculation for the mercurinium ion intermediates.

  分子内烷氧汞化反应(E)-5-芳基-4-戊烯-1-醇表明，反应的区域选择性与苯环上对位取代基的Hammett常数密切相关。同时，我们也观察到溶剂对区域选择性产生了较大的影响。这些结果与β-甲基苯乙烯类似物的甲氧基汞化反应进行了比较。区域选择性不仅讨论了空间效应，还涉及了根据汞鎓离子中间体的分子轨道计算所提出的电子效应。
• Iron-Catalyzed π-Activated C-O Ether Bond Cleavage with C-C and C-H Bond Formation
  作者：Xiaohui Fan、Xiao-Meng Cui、Yong-Hong Guan、Lin-An Fu、Hao Lv、Kun Guo、Hong-Bo Zhu

  DOI：10.1002/ejoc.201301372

  日期：2014.1

  A novel and efficient allylic alkylation reaction between π-activated ethers and allylsilane was realized under mild conditions through iron(III)-catalyzed C–O ether bond cleavage. The present protocol provides an attractive approach for the construction of sp3–sp3 C–C bonds and can be potentially applied for the selective reduction of benzyl and allyl ethers to their corresponding hydrocarbon compounds

  通过铁（III）催化的 C-O 醚键断裂，在温和条件下实现了 π 活化醚和烯丙基硅烷之间新型高效的烯丙基烷基化反应。本协议为构建 sp3-sp3 C-C 键提供了一种有吸引力的方法，并且可以通过使用三乙基硅烷作为氢化物转移试剂将苄基和烯丙基醚选择性还原为其相应的碳氢化合物。
• Iron-catalyzed N-alkylation using π-activated ethers as electrophiles
  作者：Xiaohui Fan、Lin-An Fu、Na Li、Hao Lv、Xiao-Meng Cui、Yuan Qi

  DOI：10.1039/c3ob27128e

  日期：——

  A new method for the synthesis of diverse N-alkylation compounds was developed via an iron-catalyzed etheric Csp3–O cleavage with the C–N bond formation in the reaction of π-activated ethers with various nitrogen-based nucleophiles. In addition, the mechanism of this reaction was investigated.

  通过铁催化的醚类Csp3–O键断裂并伴随C–N键形成反应，开发了一种合成多种N-烷基化化合物的新方法，即在π活性醚与各种含氮亲核试剂的反应中生成C–N键。此外，还研究了该反应的机理。
• Photo-oxidative dealkylation of α-alkylbenzyl methyl ethers induced by titanium dioxide in acetonitrile
  作者：Marta Bettoni、Tiziana Del Giacco、Cesare Rol、Giovanni V. Sebastiani

  DOI：10.1002/poc.991

  日期：2006.1

  heterogeneity, the E/C ratio data were compared with those obtained from an electron-transfer photosensitised [by 9,10-dicyanoanthracene (DCA)] oxidation in a homogeneous phase. A significant confirmation of the mechanism, in both deaerated and aerated media, was obtained by the reaction performed from 4-methoxy-α-ethylbenzyl methyl ether (as a model) in the presence of H218O, sensitised by either TiO2

  在脱气的CH 3 CN中进行TiO 2敏化的α-烷基苄基甲基醚的光氧化反应，得到了预期的相应酮，而在充气介质中，相对于酮，以脱烷基化化合物（苯甲酸甲酯）为主要产物，或独家产品（当烷基为叔丁基时）。产物分析和分布以及相对反应性的定性估计表明，脱气CH 3中的机理CN与先前对非α-烷基化的苄基醚所假设的相同；特别地，羰基化合物应通过将苄基（通过阳离子的去质子化获得）氧化成相应的阳离子而形成。为了证明在充气介质中形成苯甲酸甲酯是合理的假设，即α-烷基-α-甲氧基苄基过氧自由基（由氧竞争性地攻击苄基获得）经历了脱烷基过程；特别地，该中间体作为叔过氧自由基可以形成二聚体，该二聚体演变成相应的氧自由基，从而通过β-断裂过程得到酯。通过评估酯/羰基（E / C）摩尔比与苄基自由基中间体的绝热电离电势之间的关系，可以证实在充气介质中提出的一般机理。为了评估介质异质性的影响，将E / C比数据与通过均相中的电子转移光敏[通过9
• Transition metal-free approach for late-stage benzylic C(sp³)–H etherifications and esterifications
  作者：Yu Zhang、Prakash Kumar Sahoo、Peng Ren、Yuman Qin、Robin Cauwenbergh、Philippe Nimmegeers、Gandhi SivaRaman、Steven Van Passel、Andrea Guidetti、Shoubhik Das

  DOI：10.1039/d2cc02661a

  日期：——

  We report a transition metal-free approach for the regioselective functionalization of benzylic C(sp3)–H bonds using alcohols and carboxylic acids as the nucleophiles. This straightforward and general route has provided various benzylic ethers and esters, including twelve pharmaceutically relevant compounds.

  我们报告了一种使用醇和羧酸作为亲核试剂对苄基 C(sp 3 )-H 键进行区域选择性功能化的无过渡金属方法。这种简单而通用的途径提供了各种苄基醚和酯，包括十二种药学相关化合物。