dimethyl(p-bromobenzylidene)aminoacetal | 1009309-65-2

• 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: dimethyl(p-bromobenzylidene)aminoacetal
• 英文别名: Dimethyl-(p-Brombenzyliden)-aminoacetal；(E)-N-(4-bromobenzylidene)-2,2-dimethoxyethanamine；1-(4-bromophenyl)-N-(2,2-dimethoxyethyl)methanimine
• CAS: 1009309-65-2
• 化学式: C₁₁H₁₄BrNO₂
• 分子量: 272.142
• InChiKey: ILGOOXRFTJHHQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  3

反应信息

• 作为反应物：
  描述：

  dimethyl(p-bromobenzylidene)aminoacetal 在 氯甲酸乙酯 、 三甲氧基磷 作用下， 以4%的产率得到6-溴异喹啉
  参考文献：
  名称：

  Fluorescence of amphiphilic hemicyanine dyes without free double bonds

  摘要：

  Amphiphilic hemicyanine dyes were obtained by coupling unpolar derivatives of aniline and naphthylamine, respectively, to polar derivatives of pyridinium and isoquinolinium, respectively. These dyes have no free double bond that is prone to photoisomerization. They are effective voltage-sensitive probes in biomembranes. The dyes were characterized by their spectra of absorption and by the spectra, the quantum yields, and the lifetimes of fluorescence. (i) An enhanced polarity of solvents shifts the absorption to the blue and the fluorescence to the red. The solvatochromism is described by an enhancement of the Stokes shift at an invariant 00 energy. (ii) An enhanced polarity lowers the quantum yield of fluorescence by orders of magnitude. The effect is described by an enhancement of nonradiative deactivation at an invariant radiative decay. The enhancements of the Stokes shift and of the nonradiative decay are assigned to two types of intramolecular charge-transfer that couple to polar solvents. The first one is induced by electronic excitation. The second one is induced by intramolecular twist in the excited state. The properties of the dyes in amphiphilic assemblies are discussed in terms of their properties in bulk solvents.

  DOI：

  10.1021/j100119a048
• 作为产物：
  描述：

  对溴苯甲醛 、 氨基乙醛缩二甲醇 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 dimethyl(p-bromobenzylidene)aminoacetal
  参考文献：
  名称：

  一锅法合成多环喹啉的非对映选择性分子内环化/波瓦罗夫反应级联

  摘要：

  通过原位产生的2-氧代咪唑阳离子的Povarov反应，开发了合成复杂的类生物碱氮杂杂环化合物的方法。该反应导致形成 2 个 C-N、2 个 C-C 键和三个立体中心，具有优异的区域和非对映选择性。基于对照实验和量子化学数据，提出了反应环化的机理，并对非对映选择性的起源进行了合理化解释。此外，已经使用相同的方法实现了难以获得的 4,4'-bi(imidazol-2-one) 衍生物的直接合成。

  DOI：

  10.1039/d2ob01031c

文献信息

• Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 2. Structure-activity relationships at the phenethylamine binding site
  作者：Lawrence I. Kruse、Carl Kaiser、Walter E. DeWolf、James S. Frazee、Stephen T. Ross、Joyce Wawro、Merrie Wise、Kathryn E. Flaim、John L. Sawyer

  DOI：10.1021/jm00386a008

  日期：1987.3

  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.
• Fluorescence of amphiphilic hemicyanine dyes without free double bonds
  作者：Heinz Ephardt、Peter Fromherz

  DOI：10.1021/j100119a048

  日期：1993.4

  Amphiphilic hemicyanine dyes were obtained by coupling unpolar derivatives of aniline and naphthylamine, respectively, to polar derivatives of pyridinium and isoquinolinium, respectively. These dyes have no free double bond that is prone to photoisomerization. They are effective voltage-sensitive probes in biomembranes. The dyes were characterized by their spectra of absorption and by the spectra, the quantum yields, and the lifetimes of fluorescence. (i) An enhanced polarity of solvents shifts the absorption to the blue and the fluorescence to the red. The solvatochromism is described by an enhancement of the Stokes shift at an invariant 00 energy. (ii) An enhanced polarity lowers the quantum yield of fluorescence by orders of magnitude. The effect is described by an enhancement of nonradiative deactivation at an invariant radiative decay. The enhancements of the Stokes shift and of the nonradiative decay are assigned to two types of intramolecular charge-transfer that couple to polar solvents. The first one is induced by electronic excitation. The second one is induced by intramolecular twist in the excited state. The properties of the dyes in amphiphilic assemblies are discussed in terms of their properties in bulk solvents.
• Diastereoselective intramolecular cyclization/Povarov reaction cascade for the one-pot synthesis of polycyclic quinolines
  作者：E. A. Kuznetsova、A. V. Smolobochkin、T. S. Rizbayeva、A. S. Gazizov、J. K. Voronina、O. A. Lodochnikova、D. P. Gerasimova、A. B. Dobrynin、V. V. Syakaev、D. N. Shurpik、I. I. Stoikov、A. R. Burilov、M. A. Pudovik、O. G. Sinyashin

  DOI：10.1039/d2ob01031c

  日期：——

  method for the synthesis of complex alkaloid-like aza-heterocycles has been developed through the Povarov reaction of in situ generated 2-oxoimidazolium cations. The reaction lead to the formation of 2 C–N, 2 C–C bonds and three stereocentres, and features excellent regio- and diastereoselectivity. Based on the controlled experiments and quantum chemistry data, the mechanism of the reaction cyclization

  通过原位产生的2-氧代咪唑阳离子的Povarov反应，开发了合成复杂的类生物碱氮杂杂环化合物的方法。该反应导致形成 2 个 C-N、2 个 C-C 键和三个立体中心，具有优异的区域和非对映选择性。基于对照实验和量子化学数据，提出了反应环化的机理，并对非对映选择性的起源进行了合理化解释。此外，已经使用相同的方法实现了难以获得的 4,4'-bi(imidazol-2-one) 衍生物的直接合成。