2-((4-methoxyphenyl)amino)-2-methylpropanenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((4-methoxyphenyl)amino)-2-methylpropanenitrile
• 英文别名: 2-[(4-Methoxyphenyl)amino]-2-methylpropanenitrile；2-(4-methoxyanilino)-2-methylpropanenitrile
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: JKMJJKBDBUNCSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-chloroethyl)cyclobutan-1-one 、 2-((4-methoxyphenyl)amino)-2-methylpropanenitrile 以 乙腈 为溶剂， 反应 72.0h， 以62%的产率得到2-(4-methoxyphenyl)-2-azabicyclo[3.1.1]heptane-1-carbonitrile
  参考文献：
  名称：

  通过动态加成-分子内取代序列合成各种 2-烷基-2-氮杂双环[3.1.1]庚烷-1-腈

  摘要：

  描述了一种改进的 3-(2-氯乙基) 环丁酮的两步合成方法，并用于合成一类 2-烷基-2-氮杂双环 [3.1.1] 庚烷-1-腈。关键步骤包括将氰化氢可逆地添加到原位生成的亚胺上，然后进行分子内亲核取代，从而以中等至良好的产率 (47-92%) 生成双环骨架。这些双环化合物是稳定的，使用氢化铝锂可以很容易地将引入的氰基以高产率 (93-99%) 还原为相应的氨基甲基。

  DOI：

  10.1055/s-0030-1260811
• 作为产物：
  描述：

  甲氧苯胺 、 N-氰基-N'-甲基乙脒 在 titanium(IV) isopropylate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以42%的产率得到2-((4-methoxyphenyl)amino)-2-methylpropanenitrile
  参考文献：
  名称：

  氰基借：钛与胺的氰醇直接胺化和对映选择性实例。

  摘要：

  开发了通过催化氰基借位反应将氰醇与胺直接胺化的方法。该转化具有广泛的底物范围，出色的官能团相容性以及非常温和和简单的操作。此外，由奎宁和（S）-BINOL配体负载的钛催化剂能够实现不对称的氰基-借位反应，具有中等至高的对映选择性。

  DOI：

  10.1039/c9cc08576a

文献信息

• Synthesis of Hindered Anilines: Three-Component Coupling of Arylboronic Acids, <i>tert</i>-Butyl Nitrite, and Alkyl Bromides
  作者：David J. Fisher、James B. Shaum、C. Landon Mills、Javier Read de Alaniz

  DOI：10.1021/acs.orglett.6b02523

  日期：2016.10.7

  The synthesis of sterically hindered amines has been a significant challenge in organic chemistry. Herein, we report a modular, three-component coupling that constructs two carbon–nitrogen bonds including a sterically hindered Csp3–N bond using commercially available materials. This process uses an earth-abundant copper catalyst and mild reaction conditions, allowing access to a variety of complex

  位阻胺的合成一直是有机化学中的重大挑战。在本文中，我们报告了一种模块化的三组分偶联剂，该偶联剂使用市售材料构建了两个碳-氮键，包括空间受阻的C sp 3 -N键。该工艺使用了富含地球的铜催化剂和温和的反应条件，可使用各种复杂的芳香胺。
• Bucherer; Grolee, Chemische Berichte, 1906, vol. 39, p. 992
  作者：Bucherer、Grolee

  DOI：——

  日期：——
• Magnetic Solid Sulfonic Acid Decorated with Hydrophobic Regulators: A Combinatorial and Magnetically Separable Catalyst for the Synthesis of α-Aminonitriles
  作者：Akbar Mobaraki、Barahman Movassagh、Babak Karimi

  DOI：10.1021/co500022g

  日期：2014.7.14

  A three-component, Strecker reaction of a series of aldehydes or ketones, amines, and trimethylsilyl cyanide for the synthesis of alpha-aminonitriles in the presence of a catalytic amount of a magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H under solvent-free conditions have been investigated. This catalyst, with a combination of hydrophobicity and acidity on the Fe3O4@SiO2 core-shell of the magnetic nanobeads, as well as its water-resistant property, enabled easy mass transfer and catalytic activity in the Strecker reaction. The catalyst was easily separated by an external magnet and the recovered catalyst was reused in 6 successive reaction cycles without any significant loss of activity.
• MDM2-BASED MODULATORS OF PROTEOLYSIS AND ASSOCIATED METHODS OF USE
  申请人：Arvinas Operations, Inc.

  公开号：US20220127279A1

  公开（公告）日：2022-04-28

  The description relates to MDM2 binding compounds, including bifunctional compounds comprising the same, which find utility as modulators of targeted ubiquitination, especially inhibitors of a variety of polypeptides and other proteins which are degraded and/or otherwise inhibited by bifunctional compounds according to the present invention. In particular, the description provides compounds, which contain on one end a ligand which binds to the MDM2 E3 ubiquitin ligase and on the other end a moiety which binds a target protein such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of that protein. Compounds can be synthesized that exhibit a broad range of pharmacological activities consistent with the degradation/inhibition of targeted polypeptides of nearly any type.
• Synthesis of a Variety of 2-Alkyl-2-Azabicyclo[3.1.1]heptane-1-carbonitriles via a Dynamic Addition-Intramolecular Substitution Sequence
  作者：Christian Stevens、Ann De Blieck

  DOI：10.1055/s-0030-1260811

  日期：2011.7

  An improved two-step synthetic approach towards 3-(2-chloroethyl) cyclobutanone is described and used in the synthesis of a class of 2-alkyl-2-azabicyclo[3.1.1]heptane-1-carbonitriles. The key step consists of a reversible addition of hydrogen cyanide onto the in situ generated imines, followed by an intramolecular nucleophilic substitution, thereby leading to the bicyclic skeleton in moderate to good

  描述了一种改进的 3-(2-氯乙基) 环丁酮的两步合成方法，并用于合成一类 2-烷基-2-氮杂双环 [3.1.1] 庚烷-1-腈。关键步骤包括将氰化氢可逆地添加到原位生成的亚胺上，然后进行分子内亲核取代，从而以中等至良好的产率 (47-92%) 生成双环骨架。这些双环化合物是稳定的，使用氢化铝锂可以很容易地将引入的氰基以高产率 (93-99%) 还原为相应的氨基甲基。