1-(乙氧基甲基)-4-甲基苯 | 54191-22-9

• 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-(乙氧基甲基)-4-甲基苯
• 英文名称: 1-(ethoxymethyl)-4-methylbenzene
• 英文别名: 4-methyl-1-(ethoxymethyl)benzene；1-ethoxymethyl-4-methylbenzene；Ethyl-(4-methylbenzyl)-ether；(p-methyl)benzyl-ethylether；4-methyltoluene ethyl ether；ethyl 4-methylbenzyl ether
• CAS: 54191-22-9
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: FIDCVOWDKPLFMW-UHFFFAOYSA-N

物化性质

• 沸点：
  204 °C(Press: 765 Torr)
• 密度：
  0.9329 g/cm3(Temp: 18 °C)
• 保留指数：
  1170

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-(乙氧基甲基)-4-甲基苯 在 N-羟基邻苯二甲酰亚胺 、 氧化亚氮 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以60%的产率得到对甲基苯甲醛
  参考文献：
  名称：

  A New Approach for Oxygenation Using Nitric Oxide under the Influence of N-Hydroxyphthalimide

  摘要：

  An approach for partial oxygenation through a carbocation as an intermediate was successfully developed by using nitric oxide under the influence of N-hydroxyphthalimide. Thus, a variety of benzylic ethers were converted into the corresponding partially oxidized compounds, which are difficult to prepare by conventional methods, in high yields. For example, the reaction of phthalane with NO in the presence of a catalytic amount of NHPI at 60 degrees C gave phthalaldehyde in 80% yield. The reaction was found to proceed through the formation of a hemiacetal, such as 1-hydroxyphthalane. In addition, 1,3-di-tert-butoxymethyl benzene afforded 1,3-benzenedicarbaldehyde in good yield. On the other hand, isochroman was converted into 1,1'-oxodiisochromane under these reaction conditions. The reaction of ethers with NO in the presence of a NHPI catalyst is thought to proceed via the formation of a carbocation as an intermediate. A possible reaction path was suggested.

  DOI：

  10.1021/jo982406o
• 作为产物：
  描述：

  1-(carbomethoxy)-1,4-cyclohexadiene 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 苄基三乙基氯化铵 、 silver nitrate 、 三乙胺 作用下， 以 四氯化碳 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 62.5h， 生成 1-(乙氧基甲基)-4-甲基苯
  参考文献：
  名称：

  Regioselective ring opening in substituted benzocyclopropenes. An alternative or complementary mechanism for electrophilic substitution involving attack at .alpha. bond

  摘要：

  DOI：

  10.1021/ja00543a032

文献信息

• A Versatile Iridium(III) Metallacycle Catalyst for the Effective Hydrosilylation of Carbonyl and Carboxylic Acid Derivatives
  作者：Yann Corre、Vincent Rysak、Xavier Trivelli、Francine Agbossou-Niedercorn、Christophe Michon

  DOI：10.1002/ejoc.201700801

  日期：2017.9.1

  IrIII metallacycle rapidly and selectively catalyses the reduction of various esters, carboxylic acids, ketones, and aldehydes. The reactions proceed in high yields at room temperature by hydrosilylation followed by desilylation. Depending on the substrate, esters are reduced to alcohols or ethers and carboxylic acids to alcohols or aldehydes.

  通用的Ir III金属环可快速，选择性地催化各种酯，羧酸，酮和醛的还原。该反应在室温下通过氢化硅烷化然后脱甲硅烷基化以高收率进行。取决于底物，酯被还原为醇或醚，而羧酸被还原为醇或醛。
• Highly efficient indium-catalyzed chemoselective allylation–etherification and reductive etherification of aromatic aldehydes with functional silanes
  作者：Ming-Song Yang、Li-Wen Xu、Hua-Yu Qiu、Guo-Qiao Lai、Jian-Xiong Jiang

  DOI：10.1016/j.tetlet.2007.11.062

  日期：2008.1

  Indium(III) chloride is an effective Lewis acid catalyst for one-pot allylation–etherification and reductive etherification of aromatic aldehydes with functional silanes, allyltriethoxysilane, and triethoxysilane, at room temperature to afford corresponding ethers in excellent yields. Additionally, the InCl3-catalyzed reactions in the presence of TMSCl offer significant advantages in its ease of working-up

  氯化铟（III）是一种有效的路易斯酸催化剂，可在室温下一锅化芳族醛与官能硅烷，烯丙基三乙氧基硅烷和三乙氧基硅烷的烯丙基化—醚化和还原醚化，从而以优异的收率提供相应的醚。另外，在TMSC1存在下，InCl 3催化的反应提供了明显的优点，因为其易于处理以在温和条件下制备不对称醚。
• A kinetic model for water reactivity (avoiding activities) for hydrolyses in aqueous mixtures – selectivities for solvolyses of 4-substituted benzyl derivatives in alcohol–water mixtures
  作者：T. William Bentley、In Sun Koo、Hojune Choi、Gareth Llewellyn

  DOI：10.1002/poc.1308

  日期：2008.3

  For solvolyses of various benzyl substrates in ethanol–water (EW) and methanol–water (MW) mixtures, product selectivities (S) are reported for chlorides at 75 °C defined as follows using molar concentrations: S = ([ether product]/[alcohol product]) × ([water]/[alcohol solvent]). The results support earlier evidence that solvolyses of 4-nitrobenzyl substrates are SN2 processes, which are not susceptible

  对于乙醇-水（EW）和甲醇-水（MW）混合物中各种苄基底物的溶剂化，据报道，在75°C下氯化物的产物选择性（S）定义为使用摩尔浓度，定义如下：S  =（[醚产物] / [[酒精产品]）×（[水] / [酒精溶剂]）。该结果支持了较早的证据，即4-硝基苄基底物的溶剂分解是S N 2过程，在从水到醇的整个溶剂范围内，其机械变化均不敏感。小号EW和MW在25和/或45°C时的最大热值，以及包括动力学溶剂同位素效应（KSIE）的其他动力学数据，报道了4-硝基苄基甲磺酸酯和甲苯磺酸酯的溶剂分解。提出了一个动力学模型，解释了速率和产物。通常将由于溶剂极性引起的一般介质效应与一个溶剂效应结合在一起，从而影响水和酒精分子在S N中的亲核性2反应。根据该模型，当将醇加入水中时，反应速度由于溶剂极性的降低而降低，但是水的亲核性相对于醇增加。从酒精到水的整个溶剂组成范围内的实验速率和产品数据的可用性，揭示了使用
• Highly reactive sulfinates. The synthesis, solvolysis and rearrangement of benzyl trichloromethanesulfinates
  作者：Samuel Braverman、Ytzhak Duar

  DOI：10.1016/s0040-4020(01)88389-7

  日期：1990.1

  Benzyl trichloromethanesulfinates are easily obtained by oxidation of the corresponding sulfenates, in excellent yields. Examination of their reactivity revealed some unique features. In contrast to benzyl arenesulfinates which undergo solvolysis with complete S-O bond fission, these esters undergo solvolysis with exclusive C-O bond fission, and with a rate enhancement by a factor of 6 powers of ten

  苄基三氯甲烷亚磺酸盐很容易通过氧化相应的亚磺酸盐而获得，产率很高。检查它们的反应性显示出一些独特的特征。与通过完全SO键裂变进行溶剂分解的苄基亚芳基磺酸盐相反，这些酯通过独家CO键裂变进行溶剂分解，并且速率可提高10倍6的倍数，与甲苯磺酸甲苯磺酸酯相当。类似地，与苄基亚芳基磺酸盐不同，这些酯在极性非羟基溶剂中加热时，容易重排成亚砜。已在各种条件下对这些反应进行了动力学研究，并通过检查Hammett和Winstein相关性分析了溶剂分解对取代基和溶剂作用的敏感性。讨论了两种反应的机理。
• Selective cross coupling via oxovanadium(V)-induced oxidative desilylation of benzylic silanes
  作者：Toshikazu Hirao、Takashi Fujii、Yoshiki Ohshiro

  DOI：10.1016/0040-4039(94)80034-0

  日期：1994.10

  Benzylic silanes bearing an electron-donating group at the ortho- or para-position underwent the oxovanadium(V)-induced one-electron oxidative desilylation due to low ionization potential, which was applied to the intermolecular regioselective coupling with allylic silanes or silyl enol ether.

  在邻位或对位带有给电子基团的苯甲硅烷由于低电离势而经历了氧钒（V）诱导的单电子氧化甲硅烷基化反应，该技术被用于与烯丙基硅烷或甲硅烷基烯醇醚的分子间区域选择性偶联。