4-methoxy-N-(2-phenylethylidene)benzenamine | 205647-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxy-N-(2-phenylethylidene)benzenamine
• 英文别名: N-(4-methoxyphenyl)-2-phenylethanimine
• CAS: 205647-24-1
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: WONNXVCVCHTOCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(2-phenylethylidene)benzenamine 在 正丁基锂 、 ammonium cerium(IV) nitrate 、 鹰爪豆碱 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.17h， 生成 (S)-2-苯基-1-(噻唑-2-基)乙胺
  参考文献：
  名称：

  Enantioselective Addition of Thiazolyllithiumto Aldimines with the Aid of Chiral Ligand. Asymmetric Synthesis of (S)-Doe, a Component of Marine Natural Product, Dolastatin 10

  摘要：

  The external chiral ligand mediated asymmetric reaction of thiazolyllithium with aldimines was examined. The amino ether (5) gave rise to relatively high selectivity in the reaction of phenylimine, and sparteine (6) provided high selectivity in the reaction of imines bearing an alpha-methylene group. The reaction was applied to the synthesis of (S)-Doe, a component of antileukemic marine natural product, dolastatin 10.

  DOI：

  10.3987/com-97-s(n)15
• 作为产物：
  描述：

  苯乙醇 、 甲氧苯胺 在 Mg-Al hydrotalcite doped with Fe(3+). Elemental composition: Mg - 29.4%, Al - 3.05%, Fe - 11.4%. 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 24.0h， 以32%的产率得到4-methoxy-N-(2-phenylethylidene)benzenamine
  参考文献：
  名称：

  Recyclable hydrotalcite catalysts for alcohol imination via acceptorless dehydrogenation

  摘要：

  一系列类水滑石材料对无受体醇脱氢和一锅法亚胺化的固有催化活性。

  DOI：

  10.1039/c5gc00312a

文献信息

• 3-Thiolated 2-azetidinones: synthesis and in vitro antibacterial and antifungal activities
  作者：Maaroof Zarei、Masoud Mohamadzadeh

  DOI：10.1016/j.tet.2011.05.043

  日期：2011.8

  A series of 3-thiolated β-lactams were synthesized by [2+2] ketene–imine cycloaddition reaction from S-substituted mercaptoacetic acids and Schiff bases. Then, some of the 3-methylthio β-lactams were converted to 3-(methylsulfinyl) β-lactams and 3-(methylsulfonyl) β-lactams using m-CPBA under different reaction conditions. All the compounds were characterized by spectral data and elemental analyses

  通过[2 + 2]乙烯酮-亚胺环加成反应，由S-取代的巯基乙酸和席夫碱合成了一系列3-硫醇化的β-内酰胺。然后，某些3-甲硫β内酰胺转化成3-（甲基亚磺酰基），使用β内酰胺和3-（甲磺酰基）β内酰胺米-CPBA不同的反应条件下。所有化合物均通过光谱数据和元素分析进行​​了表征，并评估了它们对包括金黄色葡萄球菌（耐甲氧西林的菌株）在内的致病菌株的体外抗菌和抗真菌活性。初步筛选结果表明，其中一些化合物具有中等至非常好的抗菌和抗真菌活性。
• Facile Synthesis and Isolation of Secondary Amines <i>via</i> a Sequential Titanium(IV)-Catalyzed Hydroamination and Palladium-Catalyzed Hydrogenation
  作者：Erica K. J. Lui、Laurel L. Schafer

  DOI：10.1002/adsc.201500861

  日期：2016.3.3

  alkyl‐substituted secondary amines has been developed. Using a bis(amidate)bis(amido)titanium(IV) precatalyst, the hydroamination of terminal alkynes with a range of amines results in the selective formation of the anti‐Markovnikov product. The crude enamine/imine mixtures are effectively hydrogenated using palladium on carbon (Pd/C) and H2 to afford the corresponding secondary amine in excellent yields.

  已开发出一种原子经济且催化的路线，用于合成芳基和烷基取代的仲胺。使用双（酰胺基）双（酰胺基）钛（IV）预催化剂，末端炔烃与一系列胺进行加氢胺化，选择性地形成了反马尔科夫尼科夫产物。使用碳载钯（Pd / C）和H 2有效地氢化粗制的烯胺/亚胺混合物，从而以优异的收率得到相应的仲胺。简单的后处理程序可以分离纯化合物，同时避免通过柱色谱法纯化。
• One-Pot AgOAc-Mediated Synthesis of Polysubstituted Pyrroles from Primary Amines and Aldehydes: Application to the Total Synthesis of Purpurone
  作者：Qingjiang Li、Aili Fan、Zhiyao Lu、Yuxin Cui、Wenhan Lin、Yanxing Jia

  DOI：10.1021/ol101644g

  日期：2010.9.17

  A simple and efficient method for the synthesis of 1,3,4-trisubstituted or 3,4-disubstituted pyrroles has been developed. The reaction represents the first time that pyrroles are synthesized directly from readily available aldehydes and amines (anilines) as starting materials. This method has been successfully applied to the rapid synthesis of purpurone.

  已经开发了一种简单有效的合成1,3,4-三取代或3,4-二取代的吡咯的方法。该反应代表首次从容易获得的醛和胺（苯胺）为原料直接合成吡咯。该方法已成功地应用于紫嘌呤的快速合成。
• Regio- and Diastereoselective Decarboxylative Allylation of <i>N-</i>Aryl α-Amino Acids by Dual Photoredox/Nickel Catalysis
  作者：Jun Zheng、Christoph Nopper、Rifhat Bibi、Ali Nikbakht、Felix Bauer、Bernhard Breit

  DOI：10.1021/acscatal.2c01688

  日期：——

  Homoallylic amines are important building blocks for the synthesis of nitrogen-containing natural products. They are generally synthesized by addition of allyl metal compounds to imines. With the establishment of photoredox catalysis in organic chemistry, research interest in homoallylic amine syntheses via radical reactions has increased. Herein, we present a dual photoredox/nickel catalyzed regio-

  高烯丙基胺是合成含氮天然产物的重要组成部分。它们通常通过将烯丙基金属化合物与亚胺加成来合成。随着有机化学中光氧化还原催化的建立，通过自由基反应合成高烯丙基胺的研究兴趣增加了。在此，我们提出了N-芳基 α-氨基酸的双光氧化还原/镍催化的区域选择性和非对映选择性烯丙基化反应。我们的方法以高产率和高合成能力产生支链高烯丙基胺在温和和氧化还原中性条件下的非对映选择性。我们反应的合成灵活性在广泛的底物范围内得到证明，其特点是具有高官能团耐受性。详细的机理研究表明，亚胺是该反应的关键中间体。
• Polystyrene-supported TBD as an efficient and reusable organocatalyst for cyanosilylation of aldehydes, ketones, and imines
  作者：Satoru Matsukawa、Syohei Fujikawa

  DOI：10.1016/j.tetlet.2011.12.070

  日期：2012.2

  Polystyrene-supported TBD (PS-TBD) catalyzes cyanosilylation of both aldehydes and ketones using TMSCN to give the corresponding products in high yields. Imines were also converted into the desired alpha-cyanoanimes under the same conditions. PS-TBD was easily recovered and reused without significant loss of catalytic activity. (C) 2011 Elsevier Ltd. All rights reserved.