N-<(3-fluorophenyl)methylene>-2,2-dimethoxyethanamine | 73261-94-6

• 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: N-<(3-fluorophenyl)methylene>-2,2-dimethoxyethanamine
• 英文别名: N-(2,2-dimethoxyethyl)-3-fluorobenzylideneamine；N-(2,2-dimethoxyethyl)-1-(3-fluorophenyl)methanimine
• CAS: 73261-94-6
• 化学式: C₁₁H₁₄FNO₂
• 分子量: 211.236
• InChiKey: QAQHBQWRMSEULO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(3-fluorophenyl)methylene>-2,2-dimethoxyethanamine 在 双氧水 、 氯甲酸乙酯 、 乙酸酐 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 7-氟-1-异喹啉酮
  参考文献：
  名称：

  [EN] ACTIVATORS OF AUTOPHAGIC FLUX AND PHOSPHOLIPASE D AND CLEARANCE OF PROTEIN AGGREGATES INCLUDING TAU AND TREATMENT OF PROTEINOPATHIES
  [FR] ACTIVATEURS DE FLUX AUTOPHAGIQUE ET DE PHOSPHOLIPASE D ET CLAIRANCE D'AGRÉGATS DE PROTÉINES COMPRENANT TAU ET TRAITEMENT DE PROTÉINOPATHIES

  摘要：

  公开号：

  WO2017062500A3
• 作为产物：
  描述：

  氨基乙醛缩二甲醇 、 3-氟苯甲醛 反应 0.33h， 生成 N-<(3-fluorophenyl)methylene>-2,2-dimethoxyethanamine
  参考文献：
  名称：

  Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 2. Structure-activity relationships at the phenethylamine binding site

  摘要：

  1-Aralkylimidazole-2-thiones have been shown to be potent multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1). In the present study, a series of 1-benzylimidazole-2-thiones was prepared to explore the effects of substitution in the benzyl ring on the inhibition of DBH. A detailed structure-activity relationship for in vitro activity was discovered and this was shown by a modified Hansch analysis to correlate (r = 0.91) with four key structural features of the benzyl ring: the presence of a hydroxyl at the 4-position, molar refractivity at the 3-, 4-, and 5-positions, inductive effects of the substituents at the 3-, 4-, and 5-positions, and pi-electron density. The affinity (Kis) of eight substituted inhibitors for DBH was shown to correlate (r = 0.75) with the affinity (KD) of comparably substituted tyramines for the ternary DBH-oxygen-tyramine complex. This correlate is used to support the hypothesis that binding of inhibitor to DBH occurs in a fashion that mimics the binding of tyramine substrates. The most potent inhibitors were selected for study in vivo in the spontaneously hypertensive rat model of hypertension. The changes in vascular dopamine and norepinephrine levels that resulted from oral administration of the inhibitors corresponded to the observed reduction in mean arterial blood pressure. A divergence between in vitro potency and in vivo efficacy upon oral dosing was noted and is suggested to result from an in vivo metabolic conjugation of the phenolic group of inhibitor.

  DOI：

  10.1021/jm00386a008

文献信息

• Self-modulated highly chemoselective direct-reductive-amination (DRA) of benzaldehydes straightforward to N-monosubstituted benzylamine hydrochlorides
  作者：Lixin Xing、Chuanjie Cheng、Rui Zhu、Boyang Zhang、Xinyan Wang、Yuefei Hu

  DOI：10.1016/j.tet.2008.09.072

  日期：2008.12

  All unprecedented efficient and chemoselective DRA of benzaldehydes and primary amines was developed to directly yield N-monosubstituted benzylamine hydrochlorides as single products in practically quantitative yields. The method was characterized by simply adding a few milliliters of CHCl3 in the conventional Pd-C catalytic hydrogenation system at atmospheric pressure and room temperature. A self-modulated system and a four-stage cyclic pathway were proposed. (C) 2008 Elsevier Ltd. All rights reserved.
• Facile synthesis of halo-substituted tetrahydroisoquinolines and tetrahydro-2-benzazepines via N-acetyl-1,2-dihydroisoquinolines
  作者：Carl D. Perchonock、Ivan Lantos、Joseph A. Finkelstein、Kenneth G. Holden

  DOI：10.1021/jo01298a038

  日期：1980.5