4-[(4-甲氧基苯基)甲基]吗啉 | 17494-29-0

• 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: 4-[(4-甲氧基苯基)甲基]吗啉
• 英文名称: 4-(4-methoxy-benzyl)-morpholine
• 英文别名: N-(4-methoxybenzyl)morpholine；4-(p-methoxybenzyl)morpholine；4-(4-Methoxybenzyl)morpholine；4-[(4-methoxyphenyl)methyl]morpholine
• CAS: 17494-29-0
• 化学式: C₁₂H₁₇NO₂
• mdl: MFCD01653013
• 分子量: 207.272
• InChiKey: OQGALYCHDSDDRW-UHFFFAOYSA-N

物化性质

• 沸点：
  110 °C(Press: 0.5 Torr)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(4-甲氧基苯基)甲基]吗啉 在 sodium tetrahydroborate 、 五甲基二乙烯三胺 、 仲丁基锂 、 三溴化硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 42.5h， 生成 3-[[2-Hydroxy-5-(morpholin-4-ylmethyl)phenyl]methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-one
  参考文献：
  名称：

  3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl ]-1,3,4-oxadiazol-2(3H)-one, BMS-191011:  Opener of Large-Conductance Ca²⁺-Activated Potassium (Maxi-K) Channels, Identification, Solubility, and SAR

  摘要：

  Compound 8a (BMS-191011), an opener of the cloned large-conductance, Ca2+-activated potassium (maxi-K) channel, demonstrated efficacy in in vivo stroke models, which led to its nomination as a candidate for clinical evaluation. Its maxi-K channel opening properties were consistent with its structural topology, being derived by combining elements from other known maxi-K openers. However, 8a suffered from poor aqueous solubility, which complicated elucidation of SAR during in vitro evaluation. The activity of 8a in in vivo stroke models and studies directed toward improving its solubility are reported herein. Enhanced solubility was achieved by appending heterocycles to the 8a scaffold, and a notable observation was made that inclusion of a simple amino group (anilines 8k and 8l) yielded excellent in vitro maxi-K ion channel opening activity and enhanced brain-to-plasma partitioning compared to the appended heterocycles.

  DOI：

  10.1021/jm061006n
• 作为产物：
  描述：

  4-(p-methoxyselenobenzoyl)morpholine 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到4-[(4-甲氧基苯基)甲基]吗啉
  参考文献：
  名称：

  使用SmI 2 -H 2 O将硒代酰胺还原为胺

  摘要：

  硒酰胺被SmI 2与H 2 O选择性还原为胺。该方法通常用于伯，仲和叔芳基和烷基硒酰胺底物，并选择性地输送胺产物。使用直接添加H 2 O活化的SmI 2在温和条件下进行还原反应，不需要额外的路易斯碱添加剂。

  DOI：

  10.1021/acs.orglett.6b03325

文献信息

• Phosphine ligands in the ruthenium-catalyzed reductive amination without an external hydrogen source
  作者：Maria Makarova、Oleg I. Afanasyev、Fedor Kliuev、Yulia V. Nelyubina、Maria Godovikova、Denis Chusov

  DOI：10.1016/j.jorganchem.2021.121806

  日期：2021.6

  A systematic study of the phosphine additives influence on the activity of a ruthenium catalyst in reductive amination without an external hydrogen source was carried out. [CymeneRuCl2]2 was used as a reference catalyst, and a broad set of phosphines including Alk3P, Alk2ArP, Ar3P and X3P was screened. Three complexes of general formula (Cymene)RuCl2PR3 were isolated in a pure form, and their catalytic

  在没有外部氢源的情况下，对膦添加剂对钌催化剂在还原胺化中的活性的影响进行了系统的研究。[CymeneRuCl 2 ] 2用作参考催化剂，并筛选出包括Alk 3 P，Alk 2 ArP，Ar 3 P和X 3 P在内的各种膦。以纯形式分离了三种通式（Cymene）RuCl 2 PR 3的配合物，并将其催化活性与原位进行了比较生成的复合体。发现具有电子受体基团的无阻碍的三芳基膦是最透视的活化剂，大约增加了催化剂的活性。六倍，Alk 2 ArP配体的影响较小，而三烷基膦使钌催化剂失活。
• Selective cross-coupling of amines by alumina-supported palladium nanocluster catalysts
  作者：Ken-ichi Shimizu、Katsuya Shimura、Keiichiro Ohshima、Masazumi Tamura、Atsushi Satsuma

  DOI：10.1039/c1gc15835j

  日期：——

  Al2O3-supported Pd nanoclusters with an average particle size of 1.8 nm act as a reusable catalyst for the selective cross-coupling of amines. The reaction is a structure-sensitive reaction, demanding coordinatively unsaturated Pd atoms on a metallic nanocluster. The support also affects the activity, an amphoteric oxide (Al2O3) is most effective.

  平均粒径为1.8纳米的氧化铝负载钯纳米团簇可作为氨基的选择性交叉偶联反应的可重复使用催化剂。该反应对结构敏感，需要金属纳米团簇上配位不饱和的钯原子。载体也对活性有影响，两性氧化物（Al2O3）效果最佳。
• Alkylation of cyclic amines with alcohols catalyzed by Ru(II) complexes bearing N -Heterocyclic carbenes
  作者：Öznur Doğan Ulu、Nevin Gürbüz、İsmail Özdemir

  DOI：10.1016/j.tet.2017.09.027

  日期：2018.2

  includes the synthesis of 2-(1,3-dioxane-2-yl)ethyl substituted benzimidazole substituted N-heterocyclic carbenes precursors and their ruthenium complexes. Synthesized compounds were characterized by elemental analysis and NMR spectroscopy. All complexes have been tested in the alkylation of pyrrolidine and morpholine with alcohols, showing an excellent activity in this reaction.

  本文包括2-（1,3-二恶烷-2-基）乙基取代的苯并咪唑取代的N-杂环卡宾前体及其钌配合物的合成。合成的化合物通过元素分析和NMR光谱进行表征。所有配合物均已在吡咯烷和吗啉与醇的烷基化反应中进行了测试，在该反应中显示出出色的活性。
• Palladium nanoparticles stabilised by cinchona-based alkaloids in glycerol: efficient catalysts for surface assisted processes
  作者：A. Reina、C. Pradel、E. Martin、E. Teuma、M. Gómez

  DOI：10.1039/c6ra19230k

  日期：——

  Cinchona-based alkaloids led to well-dispersed palladium nanoparticles in neat glycerol, leading to efficient eco-friendly catalytic phases in hydrogenations and hydrodehalogenations.

  基于金鸡纳碱的化合物在纯甘油中导致钯纳米颗粒良好分散，从而在氢化和脱卤反应中形成高效环保的催化相。
• Carbon monoxide-driven osmium catalyzed reductive amination harvesting WGSR power
  作者：Klim O. Biriukov、Mikhail M. Vinogradov、Oleg I. Afanasyev、Dmitry V. Vasilyev、Alexey A. Tsygankov、Maria Godovikova、Yulia V. Nelyubina、Dmitry A. Loginov、Denis Chusov

  DOI：10.1039/d1cy00695a

  日期：——

  First osmium-catalyzed reductive amination under the water gas–shift reaction conditions was developed. Proposed catalytic system demonstrates high performance even at the catalyst loading as low as 0.0625 mol%.

  首次在水煤气转移反应条件下开发了铂催化的还原胺化反应。提出的催化体系表现出高性能，即使在催化剂负载量仅为0.0625 mol% 时也是如此。