2,2-dimethoxy-N-(phenylmethylene)-1-ethanamine | 54879-74-2

• 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: 2,2-dimethoxy-N-(phenylmethylene)-1-ethanamine
• 英文别名: N-(2,2-dimethoxyethyl)-1-phenylmethanimine
• CAS: 54879-74-2
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: BLRLENKSGYQRKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 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

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  2,2-dimethoxy-N-(phenylmethylene)-1-ethanamine 在 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 生成 ethyl (2,2-dimethoxyethyl)(2-(3-methoxyphenyl)-1-phenylethyl)carbamate
  参考文献：
  名称：

  Discovery of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as glutamine fructose-6-phosphate amidotransferase (GFAT) inhibitors

  摘要：

  Through high throughput screening and subsequent hit identification and optimization, we synthesized a series of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as the first reported potent and reversible GFAT inhibitors. SAR studies of this class of compounds indicated significant impact on GFAT inhibition potency by substitutions on the A-ring and C-ring. The ketone group was found to be necessary for high potency. Compound 28 (RO0509347) demonstrated potent GFAT inhibition (IC(50) = 1 mu M) with a desirable pharmacokinetic profile in rats, and showed significant efficacy in reducing the glucose excursion in an OGTT test in ob/ob mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.009
• 作为产物：
  描述：

  苯甲醛 、 氨基乙醛缩二甲醇 以 甲醇 为溶剂， 反应 16.0h， 生成 2,2-dimethoxy-N-(phenylmethylene)-1-ethanamine
  参考文献：
  名称：

  Flexible access to conformationally-locked bicyclic morpholines

  摘要：

  已经开发出一系列构象锁定双环吗啉的制备途径。这种灵活的方法允许多样化，以便从容易获得的关键构建模块合成一小批铅状支架。

  DOI：

  10.1039/c3cc45627g

文献信息

• Six-Step Gram-Scale Synthesis of the Human Immunodeficiency Virus Integrase Inhibitor Dolutegravir Sodium
  作者：Jule-Philipp Dietz、Tobias Lucas、Jonathan Groß、Sebastian Seitel、Jan Brauer、Dorota Ferenc、B. Frank Gupton、Till Opatz

  DOI：10.1021/acs.oprd.1c00139

  日期：2021.8.20

  A short and practical synthesis for preparing the active pharmaceutical ingredient dolutegravir sodium was developed. The convergent strategy starts from (R)-3-amino-1-butanol and establishes the BC ring system in a 76% isolated yield over four steps. Ring A was constructed by a one-pot 1,4-addition to diethyl-(2E/Z)-2-(ethoxymethylidene)-3-oxobutandioate and subsequent MgBr2·OEt2-mediated regioselective

  开发了一种用于制备活性药物成分多替拉韦钠的简短实用的合成方法。收敛策略从 ( R )-3-氨基-1-丁醇开始，并在四个步骤中以 76% 的分离产率建立了 BC 环系统。通过一锅1,4-加成到二乙基-( 2E / Z )-2-(乙氧基亚甲基)-3-氧代丁二酸和随后的MgBr 2 ·OEt 2介导的区域选择性环化来构建环A。与 2,4-二氟苄胺形成酰胺是通过游离羧酸或通过相应乙酯的氨解进行的。最终的盐形成通过六个线性步骤以 48-51% 的分离产率（HPLC 纯度为 99.7-99.9%）提供了多替拉韦钠。
• Curable crosslinking system with monobenzaldimine as crosslinker
  申请人：Air Products and Chemicals, Inc.

  公开号：US05451653A1

  公开（公告）日：1995-09-19

  This invention relates to improved crosslinking systems for polymeric dispersions and solutions having suitability for coatings, adhesives and use in many other applications. These systems are based upon crosslinkable polymers having a plurality of activated keto methylene groups, e.g., a beta diketone such as an acetoacetate or a keto cyano methylene functional groups and a crosslinkable component comprising an aldimine. A sufficient amount of the aldimine curing agent is used to effect reaction with the polymer containing the activated keto methylene groups and cure thereof. The improvement in the crosslinking system resides in the utilization of a monoaldimine having only one aldimine group and no other methylene reactive group as a crosslinking agent. Another improvement variation to that previously suggested comprises a redispersible polymer(s) containing activated methylene functionality and combined with the monoaldimine and the use of heterocyclic aldimine.

  本发明涉及改进的交联系统，用于适用于涂料、粘合剂和许多其他应用的聚合物分散体和溶液。这些系统基于具有多个活性酮甲基基团的可交联聚合物，例如β-二酮，例如乙酰乙酸盐或酮基氰甲基功能基团以及包含醛胺的可交联组分。使用足够量的醛胺固化剂与含有活性酮甲基基团的聚合物反应并使其固化。该交联系统的改进在于利用只有一个醛胺基团且没有其他亚甲基反应基团的单醛胺作为交联剂。先前提出的另一个改进变体包括含有活性亚甲基功能性并与单醛胺组合以及使用杂环醛胺的可再分散聚合物。
• A Convenient Synthesis of Indole-Substituted 2-Pyrrolidones and Their Cyclized Derivatives
  作者：Michel Boisbrun、Laurent Jeannin、Loïc Toupet、Jean-Yves Laronze

  DOI：10.1002/1099-0690(200009)2000:17<3051::aid-ejoc3051>3.0.co;2-3

  日期：2000.9

  Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, depending on the starting material. Derivative 18a was transformed into pyrrolo[3',4' :5,6]pyrido[3,4-b]indol-3(2H)-ones 19a and 20a by a Pictet-Spengler condensation with benzaldehyde.
• 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.
• Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 1. Some 1-phenyl and 1-phenyl-bridged derivatives of imidazole-2-thione
  作者：Lawrence I. Kruse、Carl Kaiser、Walter E. DeWolf、James S. Frazee、Eleanor Garvey、Eileen L. Hilbert、Wayne A. Faulkner、Kathryn E. Flaim、John L. Sawyer、Barry A. Berkowitz

  DOI：10.1021/jm00162a008

  日期：1986.12

  The synthesis and characterization of some 1-(phenylalkyl)imidazole-2-thiones as a novel class of "multisubstrate" inhibitors of dopamine beta-hydroxylase (DBH) are described. These inhibitors incorporate structural features that resemble both tyramine and oxygen substrates, and as evidenced by steady-state kinetics, they appear to bind both the phenethylamine binding site and the active site copper atom(s) in DBH. A series of structural congeners that incorporate different bridging chain lengths between the phenyl ring (dopamine mimic) and the imidazole-2-thione group (oxygen mimic) define the optimum distance for inhibitory potency and the likely intersite distance in the DBH active site. Additional bridging analogues were prepared to determine the active site bulk tolerance and the effects of heteroatom replacement.