N-[(1E)-(4-methoxyphenyl)methylene]methanamine | 60682-83-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[(1E)-(4-methoxyphenyl)methylene]methanamine
• 英文别名: N-methyl 4-methoxybenzaldimine
• CAS: 60682-83-9
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: LWWBBDFBZJCKHQ-JXMROGBWSA-N

物化性质

• 沸点：
  129-130 °C(Press: 18 Torr)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-[(1E)-(4-methoxyphenyl)methylene]methanamine 在 cesium fluoride 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 35.0h， 生成 dimethyl 1-methyl-2-(4-methoxyphenyl)-3-pyrroline-3,4-dicarboxylate
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 19. Synthesis and antineoplastic activity of bis[[[(alkylamino)carbonyl]oxy]methyl]-substituted 3-pyrrolines as prodrugs of tumor inhibitory pyrrolebis(carbamates)

  摘要：

  A series of bis[(carbamoyloxy)methyl]pyrrolines 2-4 were synthesized from either the appropriate alpha-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions. The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles. The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive. The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the corresponding phenylpyrroles all showed comparable activity. The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole. Electron-withdrawing substituents on the phenyl ring appear to retard this process.

  DOI：

  10.1021/jm00161a019
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 甲胺 以 甲醇 为溶剂， 反应 15.0h， 以91%的产率得到N-[(1E)-(4-methoxyphenyl)methylene]methanamine
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 19. Synthesis and antineoplastic activity of bis[[[(alkylamino)carbonyl]oxy]methyl]-substituted 3-pyrrolines as prodrugs of tumor inhibitory pyrrolebis(carbamates)

  摘要：

  A series of bis[(carbamoyloxy)methyl]pyrrolines 2-4 were synthesized from either the appropriate alpha-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions. The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles. The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive. The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the corresponding phenylpyrroles all showed comparable activity. The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole. Electron-withdrawing substituents on the phenyl ring appear to retard this process.

  DOI：

  10.1021/jm00161a019

文献信息

• Functionalized β-Thiolactams by Lewis Acid Catalyzed Addition of Alkynyl Silyl Sulfides to Azomethines
  作者：Wolf-Rüdiger Förster、Rainer Isecke、Carsten Spanka、Ernst Schaumann

  DOI：10.1055/s-1997-1275

  日期：1997.8

  Thiophilic Lewis acids (e.g. zinc iodide) have a pronounced catalytic effect on the formal [2+2] cycloaddition of alkynyl silyl sulfides 2 and Schiff bases 3 to give 2-azetidinethiones 4. In contrast to uncatalyzed reactions, a large number of functionalities is tolerated and yields are significantly improved.

  亲硫路易斯酸（例如碘化锌）对炔基硅硫化物 2 和席夫碱 3 的正式 [2+2] 环加成反应具有明显的催化作用，生成 2-氮杂环丁烷硫醇 4。与未催化的反应相比，能够容忍大量功能团，产率显著提高。
• Inverse-electron-demand Diels–Alder reactions of 4-aryl-2-pyrones with electron-rich dienophiles
  作者：László Balázs、István Kádas、László Tõke

  DOI：10.1016/s0040-4039(00)01302-2

  日期：2000.9

  The Diels–Alder reaction of 4-aryl-pyrones with electron-rich dienophiles afforded substituted biaryl derivatives in most cases. At the minimal temperatures necessary for a measurable conversion of the starting pyrones, the bicyclic lactones, the primary products of the condensation, underwent cycloreversion by extruding carbon dioxide and then aromatised through further eliminations. In the case of

  在大多数情况下，4-芳基-吡喃酮与富电子的亲二烯体的狄尔斯-阿尔德反应可得到取代的联芳基衍生物。在可测量的起始吡喃酮转化所必需的最低温度下，双环内酯（缩合的主要产物）通过挤出二氧化碳进行环还原，然后通过进一步消除芳香化。在活性更高的4-芳基-6-氯吡喃酮的情况下，观察到正式的取代，而不是预期的用活性的亲二烯体进行环加成，而在其与席夫碱的反应中，环加成的主要产物被捕获。形成新的四氢吡啶衍生物。
• A Highly Efficient Carbon−Carbon Bond Formation Reaction via Nucleophilic Addition to <i>N</i>-Alkylaldimines without Acids or Metallic Species
  作者：Hisao Nemoto、Tomoyuki Kawamura、Norikazu Miyoshi

  DOI：10.1021/ja054010h

  日期：2005.10.1

  A nucleophilic addition reaction to N-methylaldimines without acid or metal species is described. A novel reagent, dicyanomethyl acetate, is used as a nucleophile to give alpha-(N-methyl-N-acetyl)amino acid methyl esters in excellent yield.

  描述了在没有酸或金属物质的情况下对 N-甲基醛亚胺进行的亲核加成反应。一种新型试剂二氰基乙酸甲酯用作亲核试剂，以优异的产率得到 α-（N-甲基-N-乙酰基）氨基酸甲酯。
• HETEROCYCLIC COMPOUND AND HARMFUL-ARTHROPOD CONTROL AGENT CONTAINING SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：US20200165244A1

  公开（公告）日：2020-05-28

  A compound represented by formula (I), which is highly effective in controlling harmful arthropods, an intermediate thereof and a production method thereof are described. In formula (I), A 1 represents CH or a nitrogen atom; R 1 represents a C1-C6 alkyl group optionally having one or more halogen atoms; R 5 represents CF 3 , C 2 F 5 , or S(O) m CF 3 ; Q represents NR 2 C(O)OR 3 or N═CR 4 R 6 ; R 2 represents a hydrogen atom or the like; R 3 represents a C1-C6 alkyl group optionally having one or more halogen atoms or the like; R 4 represents a hydrogen atom or the like; R 6 represents a phenyl group optionally having one or more substituents selected from group D, or the like; and n and m each independently are 0, 1, or 2. Group D: a group consisting of C1-C6 alkyl groups optionally having one or more halogen atoms and C1-C6 alkoxy groups optionally having one or more halogen atoms or the like.

  描述了一种由化学式（I）表示的化合物，该化合物在控制有害节肢动物方面具有高效性，以及其中间体和生产方法。在化学式（I）中，A1代表CH或氮原子；R1代表一个C1-C6烷基基团，可选地具有一个或多个卤素原子；R5代表CF3、C2F5或S(O)mCF3；Q代表NR2C(O)OR3或N═CR4R6；R2代表氢原子或类似物；R3代表一个C1-C6烷基基团，可选地具有一个或多个卤素原子或类似物；R4代表氢原子或类似物；R6代表一个苯基团，可选地具有一个或多个来自D组的取代基，或类似物；n和m各自独立地为0、1或2。D组：由C1-C6烷基基团和/或C1-C6烷氧基团等可选地具有一个或多个卤素原子的组成的组。
• Isomerization of <i>meso</i> Diamines into their <i>C</i>₂ Symmetrical <i>d,l</i> Isomers
  作者：Alexandre Alexakis、Isabelle Aujard、Pierre Mangeney

  DOI：10.1055/s-1998-1791

  日期：1998.8

  An efficient isomerization method is disclosed which allows the obtention of the useful d,l isomers of C 2 symmetrical diamines, starting from their meso isomer.

  公开了一种有效的异构化方法，该方法允许从C 2 对称二胺的内消旋异构体开始获得有用的d,l异构体。

表征谱图