α-phenyl β-dimethylaminoacrylonitrile | 70205-70-8

• 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: α-phenyl β-dimethylaminoacrylonitrile
• 英文别名: 3-(dimethylamino)-2-phenylacrylonitrile；3-Dimethylamino-2-phenylacrylonitril；β-Dimethylamino-α-phenyl-acrylonitril；β-Dimethylamino-atropanitril；2-Phenyl-3-dimethylaminoacrylnitril；3-(Dimethylamino)-2-phenylprop-2-enenitrile
• CAS: 70205-70-8；70515-61-6；18226-50-1
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: VDKZGONUAHUVJF-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80°C
• 沸点：
  375.6±31.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  α-phenyl β-dimethylaminoacrylonitrile 在 氢溴酸肼 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 3-氨基-4-苯基-1H-吡唑
  参考文献：
  名称：

  Structure–activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors

  摘要：

  A structure-activity relationship study of dorsomorphin, a previously identified inhibitor of SMAD 1/5/8 phosphorylation by bone morphogenetic protein (BMP) type 1 receptors ALK2, 3, and 6, revealed that increased inhibitory activity could be accomplished by replacing the pendent 4-pyridine ring with 4-quinoline. The activity contributions of various nitrogen atoms in the core pyrazolo[1,5-a]pyrimidine ring were also examined by preparing and evaluating pyrrolo[1,2-a] pyrimidine and pyrazolo[1,5-a] pyridine derivatives. In addition, increased mouse liver microsome stability was achieved by replacing the ether substituent on the pendent phenyl ring with piperazine. Finally, an optimized compound 13 (LDN-193189 or DM-3189) demonstrated moderate pharmacokinetic characteristics (e.g., plasma t(1/2) = 1.6 h) following intraperitoneal administration in mice. These studies provide useful molecular probes for examining the in vivo pharmacology of BMP signaling inhibition. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.052
• 作为产物：
  描述：

  Bredereck 试剂 、 苯乙腈 以 甲苯 为溶剂， 反应 3.0h， 生成 α-phenyl β-dimethylaminoacrylonitrile
  参考文献：
  名称：

  Identification and Preliminary Characterization of a Potent, Safe, and Orally Efficacious Inhibitor of Acyl-CoA:Diacylglycerol Acyltransferase 1

  摘要：

  A high-throughput screen against human DGAT-1 led to the identification of a core structure that was subsequently optimized to afford the potent, selective, and orally bioavailable compound 14. Oral administration at doses >= 0.03 mg/kg significantly reduced postprandial triglycerides in mice following an oral lipid challenge. Further assessment in both acute and chronic safety pharmacology and toxicology studies demonstrated a clean profile up to high plasma levels, thus culminating in the nomination of 14 as clinical candidate ABT-046.

  DOI：

  10.1021/jm201524g

文献信息

• A facile, regioselective synthesis of pyrazolo[1, 5-a]pyrimidine analogs in the presence of KHSO4 in aqueous media assisted by ultrasound and their anti-inflammatory and anti-cancer activities
  作者：Shunan Kaping、Utpalparna Kalita、Melboureen Sunn、Laishram Indira Singha、Jai Narain Vishwakarma

  DOI：10.1007/s00706-015-1638-x

  日期：2016.7

  5-a]pyrimidine derivatives under ultrasound irradiation assisted by KHSO4 in aqueous medium. 3-(4-Methoxyphenyl)-3-oxopropanenitrile reacted with hydrazine hydrate in refluxing ethanol to give 5-(4-methoxyphenyl)-1H-pyrazol-3-amine. Condensation of 3-aminopyrazoles with formylated active proton compounds furnished pyrazolopyrimidines in high to excellent yield. The chemical structure and regioselectivity

  摘要描述了一种环境友好，简单，有效和方便的方法，该方法用于在水性介质中在KHSO 4辅助的超声辐射下合成新型吡唑并[1,5- a ]嘧啶衍生物。3-（4-甲氧基苯基）-3-氧代丙烷腈与水合肼在回流的乙醇中反应，得到5-（4-甲氧基苯基）-1 H-吡唑-3-胺。3-氨基吡唑与甲酰化的活性质子化合物的缩合以高至优异的产率提供了吡唑并嘧啶。通过IR，1 H NMR，13确认合成的化合物的化学结构和区域选择性1 H NMR和质谱数据。对所选化合物进行了X射线晶体学研究。此外，筛选了这些合成的化合物的抗炎和抗癌活性，结果令人鼓舞。该方案的主要优点是收率高，操作简单，反应时间短，并且没有苛刻的反应条件。 图形概要
• .beta.-Aminocinnamonitriles as potential antiinflammatory agents
  作者：S. A. Lang、E. Cohen

  DOI：10.1021/jm00238a027

  日期：1975.4

  A number of beta-aminocinnamonitriles have been prepared by the reaction of salts of acetonitrile and propionitrile with benzonitrile. These materials were evaluated in the carrageenan antiinflammatory screen in Royal Hart, Wistar strain rats. Despite good weight gains in the parent molecule, beta-aminocinnamonitrile (1), only marginal activity was found in related compounds and some possible "metabolites

  通过乙腈和丙腈的盐与苄腈的反应已经制备了许多β-氨基肉桂腈。这些材料在Wistar品系Royal Hart大鼠的角叉菜胶消炎筛选中进行了评估。尽管母体分子β-氨基肉桂腈（1）的体重增加了很多，但在相关化合物和某些可能的“代谢产物”中仅发现了少量活性。
• Regioselectivity in the Reaction of 2‐Aminobenzothiazoles and 2‐Aminobenzimidazoles with Enaminonitriles and Enaminones: Synthesis of Functionally Substituted Pyrimido[2,1‐<i>b</i>][1,3]benzothiazole and Pyrimido[1,2‐<i>a</i>]benzimidazole Derivatives
  作者：Abdulaziz Alnajjar、Mervat Mohammed Abdelkhalik、Hossam Mohammed Riad、Samia Mohammed Sayed、Kamal Usef Sadek

  DOI：10.1002/jhet.3337

  日期：2018.12

  A variety of new polyfunctionally substituted benzo[d]pyrimido[2,1‐b][1,3]thiazole and benzo[4,5]imidazo[1,2‐a]pyrimidine derivatives have been synthesized. The general synthetic procedure used for this purpose involves the condensation of 2‐aminobenzothiazole and 2‐aminobenzimidazole with a variety of enaminonitriles, enaminones, and acrylaldehyde. The regioselectivity for initial attack of either

  各种新的多官能取代的苯并[ d ]嘧啶基[2,1– b ] [1,3]噻唑和苯并[4,5]咪唑[1,2- a ]已经合成了]嘧啶衍生物。用于该目的的一般合成方法涉及2-氨基苯并噻唑和2-氨基苯并咪唑与各种烯氨基腈，烯胺和丙烯醛的缩合。研究并合理化了对环内环氮或环外氨基的初始进攻的区域选择性。可以得出结论，环氮是酸性介质中反应性最强的分子，也可以分离出环状中间体，这证明了环化后的结论。然而，在碱性或中性介质中，发现环外氨基是反应性最高的中心。尽可能通过元素分析，光谱数据和替代合成路线阐明了新合成化合物的所有结构。
• Synthesis of New [1,2,4]Triazolo[1,5-<i>a</i> ]pyrimidine Derivatives: Reactivity of 3-Amino[1,2,4]triazole towards Enaminonitriles and Enaminones
  作者：Abdulaziz Alnajjar、Mervat Mohammed Abdelkhalik、Mohamed Abdelmonem Raslan、Solwan Maher Ibraheem、Kamal Usef Sadek

  DOI：10.1002/jhet.3222

  日期：2018.7

  A diversity of new 7‐substituted[1,2,4]triazolo[1,5‐a]pyrimidine and 6‐substituted[1,2,4]triazolo[1,5‐a]pyrimidine‐7‐amine derivatives has been synthesized via reaction of 3‐amino‐[1,2,4]triazole with enaminonitriles and enaminones. The regio orientation and the structure of the products were confirmed by spectral and analytical data and synthesis via an alternative route. The procedure proved to be

  已经开发了多种新的7-取代的[1,2,4]三唑[1,5- a ]嘧啶和6-取代的[1,2,4]三唑[1,5 - a ]嘧啶-7-胺衍生物通过3-氨基[1,2,4]三唑与烯胺腈和烯胺酮的反应合成。产物的区域取向和结构通过光谱和分析数据以及通过另一种途径的合成得到证实。该方法被证明是简单，有效和高收率的，并且获得了[1,2,4]三唑并[1,5- a ]嘧啶的多样性。
• Insecticidal 5-substituted-2,4-diaminopyrimidine derivatives
  申请人：FMC Corporation

  公开号：US05627189A1

  公开（公告）日：1997-05-06

  An insecticidal composition comprising, in admixture with an agriculturally acceptable carrier, an insecticidally effective amount of a compound of the formula: ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.7, R.sup.8, m, n, and p are as defined herein, and agriculturally acceptable salts thereof, and methods of using the same.

  一种杀虫组合物，与农业可接受的载体混合，包含式子的化合物的杀虫有效量：##STR1## 其中R、R.sup.1、R.sup.2、R.sup.3、R.sup.7、R.sup.8、m、n和p如本文所定义，以及其农业可接受的盐，以及使用它们的方法。