m-methoxybenzylidenemethylamine | 16928-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: m-methoxybenzylidenemethylamine
• 英文别名: N-(3-methoxybenzylidene)methanamine；N-(3-methoxybenzylidene)-methyl-amine；1-(3-methoxyphenyl)-N-methylmethanimine；3-Methoxy-benzaldehyd-methylimid；(3-methoxy-benzylidene)-methyl-amine；(3-Methoxy-benzyliden)-methyl-amin；m-Methoxy-N-methylbenzylidenamin；Methanamine, N-[(3-methoxyphenyl)methylene]-
• CAS: 16928-30-6
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: GMYWIOGIHDHYMK-UHFFFAOYSA-N

物化性质

• 沸点：
  128 °C(Press: 26 Torr)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  m-methoxybenzylidenemethylamine 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 2-[(3-methoxy-benzyl)-methyl-amino]-1-phenyl-ethanol
  参考文献：
  名称：

  4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors

  摘要：

  Novel 4-phenyl tetrahydroisoquinolines that inhibit both dopamine and norepinephrine transporters were designed and prepared. In this Letter, we describe the synthesis, in vitro activity and associated structure-activity relationships of this series. We also report the ex vivo NET occupancy of a representative compound, 41. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.050
• 作为产物：
  描述：

  N-Chlor-N-methyl-m-methoxy-benzylamin 在 三乙胺 作用下， 反应 3.0h， 生成 m-methoxybenzylidenemethylamine
  参考文献：
  名称：

  使用胺作为亚胺的方便来源，可伸缩地一锅合成β-内酰胺环†

  摘要：

  以仲苄胺和酰氯为起始原料，设计了一种简便的合成取代β-内酰胺的方法。反应进行顺利，所有产物均以高收率获得。

  DOI：

  10.1039/c6ra02744j

文献信息

• Efficient Synthesis of New 4-Arylideneimidazolin-5-ones Related to the GFP Chromophore by 2+3 Cyclocondensation of Arylideneimines with Imidate Ylides
  作者：Janusz Kowalik、Anthony Baldridge、Laren Tolbert

  DOI：10.1055/s-0029-1218796

  日期：2010.7

  A 2+3 condensation of a wide assortment of Schiff bases, prepared from aromatic aldehydes and primary amines, with methyl 2-(1-ethoxyethylideneamino)acetate allows convenient access to an extensive family of substituted 4-arylideneimidazolin-5-one analogues of the green fluorescent protein (GFP) chromophore. 4-arylideneimidazolin-5-one - azomethine ylide - Schiff bases - heterocycle - 2+3 cycloaddition

  由芳族醛和伯胺制得的各种席夫碱与2-（1-乙氧基乙叉基氨基）乙酸甲酯的2 + 3缩合反应可方便地获得广泛的取代的4-芳基亚氨基咪唑啉-5-酮类似物家族绿色荧光蛋白（GFP）生色团。 4-芳基亚胺达唑啉-5-酮-甲亚胺叶立德-席夫碱-杂环-2 + 3环加成
• Highly Enantioselective Synthesis of Tetrahydroquinolines via Cobalt(II)-Catalyzed Tandem 1,5-Hydride Transfer/Cyclization
  作者：Weidi Cao、Xiaohua Liu、Wentao Wang、Lili Lin、Xiaoming Feng

  DOI：10.1021/ol1028282

  日期：2011.2.18

  A chiral catalyst prepared from N,N′-dioxide and Co(BF4)2·6H2O was applied in the asymmetric hydride transfer initiated cyclization reaction, giving optically active tetrahydroquinolines in good yields with high enantioselectivities under mild reaction conditions. Meanwhile, in light of the absolute configuration of the product, a possible working model was proposed to explain the origin of the activation

  将由N，N'-二氧化物和Co（BF 4）2 ·6H 2 O制备的手性催化剂用于不对称氢化物转移引发的环化反应中，在温和的反应条件下，以高收率和高对映选择性得到旋光性四氢喹啉。同时，根据产品的绝对配置，提出了可能的工作模型来解释激活和不对称感应的起源。
• A Novel Construction of 2-Benzazepine Scaffold Based on TiCl4-Mediated Tandem Mannich Reaction–Aromatic Electrophilic Substitution
  作者：Liangxi Li、Zhiming Li、Quanrui Wang

  DOI：10.1002/hlca.200900107

  日期：2009.12

  A novel construction of 2‐benzazepine derivatives based on TiCl4‐mediated tandem Mannich reaction of electron‐rich benzyl iminium ions with alkenyl ethers and Friedel–Crafts‐type alkylation is described. The protocol is amenable to provide the tricyclic furo[3,2‐d][2]benzazepine and pyrano[3,2‐d][2]benzazepine derivatives, respectively, with 2,3‐dihydrofuran or 3,4‐dihydro‐2H‐pyran as the substrates

  描述了一种基于TiCl 4介导的富电子苄基亚胺离子与链烯基醚和Friedel – Crafts型烷基化的串联曼尼希反应的新型2-苯并ze庚因衍生物的结构。该协议适用于分别为三环呋喃[3,2- d ] [2]苯并and庚因和吡喃并[3,2- d ] [2]苯并ze庚因衍生物提供2,3-二氢呋喃或3,4-二氢呋喃。 2 H-吡喃为底物。
• Three-component carboarylation of unactivated imines with arynes and carbon nucleophiles
  作者：Jing-Kun Xu、Sheng-Jun Li、Hai-Yang Wang、Wen-Cong Xu、Shi-Kai Tian

  DOI：10.1039/c6cc09311f

  日期：——

  With 2-(trimethylsilyl)aryl triflates as aryne precursors, an unprecedented three-component carboarylation reaction of unactivated imines with arynes and carbon nucleophiles has been developed to access a variety of functionalized tertiary amines...

  以2-（三甲基甲硅烷基）芳基三氟甲磺酸酯为芳烃前体，已开发出前所未有的未活化亚胺与芳烃和碳亲核试剂的三组分碳芳基化反应，以获取各种官能化叔胺。
• Formal Insertion of Imines (or Nitrogen Heteroarenes) and Arynes into the C–Cl Bond of Carbon Tetrachloride
  作者：Sheng-Jun Li、Yi Wang、Jing-Kun Xu、Dong Xie、Shi-Kai Tian、Zhi-Xiang Yu

  DOI：10.1021/acs.orglett.8b01845

  日期：2018.8.3

  The formal insertion of double and triple bonds into the C–Cl bond of carbon tetrachloride has enabled the full utilization of carbon tetrachloride in chemical synthesis. A range of unactivated imines and electron-deficient nitrogen heteroarenes served as effective sources of C=N bonds to react with arynes and carbon tetrachloride to afford functionalized anilines whose core structures are present

  正式将双键和三键插入四氯化碳的C–Cl键使得化学合成中可以充分利用四氯化碳。一系列未活化的亚胺和缺电子的氮杂芳烃可作为C = N键的有效来源，与芳烃和四氯化碳反应，提供官能化的苯胺，其苯胺结构存在于某些有价值的节肢动物杀螨剂中。对照实验和DFT计算表明涉及三氯甲基阴离子中间体。