2-methyl-2-((1-phenylethyl)amino)propane-nitrile | 882182-35-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-methyl-2-((1-phenylethyl)amino)propane-nitrile
• 英文别名: 2-methyl-2-(((1S)-1-phenylethyl)amino)propanenitrile；(S)-2-methyl-2-(1-phenylethylamino)propanenitrile；2-methyl-2-[[(1S)-1-phenylethyl]amino]propanenitrile
• CAS: 882182-35-6
• 化学式: C₁₂H₁₆N₂
• 分子量: 188.272
• InChiKey: VJGVMJATGPCNCU-JTQLQIEISA-N

物化性质

• 熔点：
  77-78 °C(Solv: hexane (110-54-3))
• 沸点：
  309.1±17.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-2-((1-phenylethyl)amino)propane-nitrile 、 双环[4.1.0]庚烷-2-酮 在 (S)-(-)-α-methylbenzylamine hydrochloride 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  An approach to 2-cyanopyrrolidines bearing a chiral auxiliary

  摘要：

  The reaction of 2-methyl-2-(1-phenylethyl)amino)propanenitrile with different gamma-halocarbonyl compounds is investigated. The influence of different parameters such as the nature of the substrate and solvent, is discussed. The reaction is considered as a convenient route to 2-cyanopyrrolidines in the case of aliphatic gamma-halocarbonyl compounds possessing a reasonably reactive carbonyl group. In many cases, the products can be obtained as single enantiomers. It is shown that cyclopropyl ketones can also react with 2-methyl-2-((1-phenylethyl)amino)propanenitrile to give 2-cyanopyrrolidines. A mechanistic scheme is proposed in order to explain the experimental facts observed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.01.008
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 丙酮氰醇 以 甲醇 为溶剂， 反应 24.0h， 以100%的产率得到2-methyl-2-((1-phenylethyl)amino)propane-nitrile
  参考文献：
  名称：

  立体选择性合成2,4-甲基脯氨酸的同系物

  摘要：

  报道了新颖的刚性双环脯氨酸类似物2-氮杂双环[2.2.1]庚烷-1-羧酸和6-氮杂双环[3.2.1]辛烷-5-羧酸的立体选择性合成。由相应的2-环烯-1-酮以五个步骤进行合成。改进了已知的2，4-甲基脯氨酸的方法。这三个氨基酸构成了构象受限的脯氨酸类似物的文库，其可用于拟肽和肽模型的设计。

  DOI：

  10.1016/j.tetasy.2005.12.009

文献信息

• NOVEL INHIBITORS OF POLY(ADP-RIBOSE)POLYMERASE (PARP)
  申请人：CHU Daniel

  公开号：US20090062268A1

  公开（公告）日：2009-03-05

  A compound having the structure set forth in Formula (I): wherein the variables Y, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein. Compounds described herein are inhibitors of poly(ADP-ribose)polymerase activity. Also described herein are pharmaceutical compositions that include at least one compound described herein and the use of such compounds and pharmaceutical compositions to treat diseases, disorders and conditions that are ameliorated by the inhibition of PARP activity.

  具有以下式（I）所示结构的化合物： 其中变量Y，R1，R2，R3，R4和R5如本文所定义。本文描述的化合物是聚(ADP-核糖)聚合酶活性的抑制剂。本文还描述了包括至少一种本文描述的化合物的药物组合物，以及利用这些化合物和药物组合物治疗通过抑制PARP活性而改善的疾病、疾病和症状。
• One-pot synthesis of α-aminonitriles from alkyl and aryl cyanides: a Strecker reaction via aldimine alanes
  作者：Szabolcs Sipos、István Jablonkai

  DOI：10.1016/j.tetlet.2009.02.004

  日期：2009.4

  A one-pot Strecker reaction using various alkyl, arylalkyl and arylnitriles is developed. Aldimine alanes were generated in situ from nitriles by the addition of diisobutylaluminium hydride, and were converted into the corresponding imines on reaction with (S)-(-)-1-phenylethylamine. Nucleophilic addition to the imines in the presence of catalytic triethylamine, using acetone cyanohydrin as a cyanide source, provided alpha-aminonitriles. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of enantiopure (R,R)- and (S,S)-cis-2,3-propanoprolines
  作者：Natalia A. Kopylova、Oleksandr O. Grygorenko、Igor V. Komarov、Ulrich Groth

  DOI：10.1016/j.tetasy.2010.11.017

  日期：2010.12

  A novel approach to the synthesis of an enantiopure bicyclic proline analogue, hexahydrocyclopentalb]pyrrole-6a(1H)-carboxylic acid ('2,3-propanoproline'), has been developed. The method relied on tandem Strecker-nucleophilic cyclization reaction of 2-(2-bromoethyl)cyclopentanone. The overall synthetic scheme included six steps and resulted in 18% overall yield of both enantiomers of the title amino acid. (C) 2010 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of 2,4-methanoproline homologues
  作者：Oleksandr O. Grygorenko、Oleksiy S. Artamonov、Gennady V. Palamarchuk、Roman I. Zubatyuk、Oleg V. Shishkin、Igor V. Komarov

  DOI：10.1016/j.tetasy.2005.12.009

  日期：2006.1

  The stereoselective synthesis of 2-azabicyclo[2.2.1]heptane-1-carboxylic acid and 6-azabicyclo[3.2.1]octane-5-carboxylic acid, novel rigid bicyclic proline analogues, is reported. The synthesis was performed in five steps from the corresponding 2-cycloalken-1-ones. A known approach to 2,4-methanoproline is improved. The three amino acids constitute a library of conformationally constrained proline

  报道了新颖的刚性双环脯氨酸类似物2-氮杂双环[2.2.1]庚烷-1-羧酸和6-氮杂双环[3.2.1]辛烷-5-羧酸的立体选择性合成。由相应的2-环烯-1-酮以五个步骤进行合成。改进了已知的2，4-甲基脯氨酸的方法。这三个氨基酸构成了构象受限的脯氨酸类似物的文库，其可用于拟肽和肽模型的设计。
• An approach to 2-cyanopyrrolidines bearing a chiral auxiliary
  作者：Oleksandr O. Grygorenko、Nataliya A. Kopylova、Pavel K. Mikhailiuk、Anja Meißner、Igor V. Komarov

  DOI：10.1016/j.tetasy.2007.01.008

  日期：2007.2

  The reaction of 2-methyl-2-(1-phenylethyl)amino)propanenitrile with different gamma-halocarbonyl compounds is investigated. The influence of different parameters such as the nature of the substrate and solvent, is discussed. The reaction is considered as a convenient route to 2-cyanopyrrolidines in the case of aliphatic gamma-halocarbonyl compounds possessing a reasonably reactive carbonyl group. In many cases, the products can be obtained as single enantiomers. It is shown that cyclopropyl ketones can also react with 2-methyl-2-((1-phenylethyl)amino)propanenitrile to give 2-cyanopyrrolidines. A mechanistic scheme is proposed in order to explain the experimental facts observed. (c) 2007 Elsevier Ltd. All rights reserved.