2-(methyl(phenyl)amino)propanenitrile | 69905-97-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(methyl(phenyl)amino)propanenitrile
• 英文别名: 2-(N-methylanilino)propanenitrile；N-(1-cyanoethyl)-N-methylaniline；N-methyl-N-phenyl-alanine nitrile；N-Methyl-N-phenyl-alanin-nitril；α-Methylanilino-propionsaeure-nitril；Methyl-(α-cyan-aethyl)-anilin；2-(N-methyl-N-phenylamino)propionitrile
• CAS: 69905-97-1
• 化学式: C₁₀H₁₂N₂
• 分子量: 160.219
• InChiKey: HAMNZIGCXKLDPH-UHFFFAOYSA-N

物化性质

• 沸点：
  272.0±23.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(methyl(phenyl)amino)propanenitrile 在 盐酸 、 sodium nitrite 作用下， 生成 N-methyl-N-(4-nitroso-phenyl)-alanine nitrile
  参考文献：
  名称：

  Sachs; Kraft, Chemische Berichte, 1903, vol. 36, p. 760

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(甲基(苯基)氨基)乙腈 在 copper(l) iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 2-(methyl(phenyl)amino)propanenitrile
  参考文献：
  名称：

  2-(N-methylanilino)-2-phenylsulfanylacetonitrile, a reagent tested for electrophilic, nucleophilic and radical reactions

  摘要：

  2-(N-Methylanilino) -2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide. Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated alpha-aminoalkenenitriles of 2E-configuration. Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates. Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by Cul or Lewis acids to give varied alpha-amino nitriles. The 4-oxo-2-amino nitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung. When 1 was treated with tributylstannane, the corresponding amino nitrile alpha-radical was formed and the self-coupling product was isolated.

  DOI：

  10.1039/p19940002217

文献信息

• One‐Pot Synthesis of α‐Amino Nitrile Units through Alkylative Strecker Cyanation from Formamides
  作者：Bao Yu、Florent Bodinier、Maximiliene Saague‐Tenefo、Patrice Gerardo、Janick Ardisson、Marie‐Isabelle Lannou、Geoffroy Sorin

  DOI：10.1002/ejoc.202100418

  日期：2021.7.7

  Easy and straightforward access to α-amino nitrile units by one-pot synthesis through a reductive Strecker cyanation from readily available formamides. The reaction is broad in scope and the conditions are mild, inexpensive, and easy to set-up, providing numerous α-amino nitriles in good yields (34 examples, 41–94 % yield).

  通过从现成的甲酰胺中进行还原性 Strecker 氰化反应，通过一锅法合成，轻松直接地获得 α-氨基腈单元。该反应范围广泛，条件温和、价格低廉且易于设置，以良好的收率提供了大量 α-氨基腈（34 个实例，41-94% 的收率）。
• Covalently hooked EOSIN-Y in a Zr(IV) framework as visible-light mediated, heterogeneous photocatalyst for efficient C H functionalization of tertiary amines
  作者：Gaurav Kumar、Pratik Solanki、Mohd Nazish、Subhadip Neogi、Rukhsana I. Kureshy、Noor-ul H. Khan

  DOI：10.1016/j.jcat.2019.02.011

  日期：2019.3

  novel heterogeneous photo-catalyst by utilizing post-synthetic modification of an amine functionalized Zr(IV) metal-organic framework (UiO-66-NH2) through covalent hooking of EOSIN-Y via dehydrating coupling. The characterization of the catalyst was accomplished by FT-IR, XRD, BET surface analysis, TGA, as well as TEM, SEM, XPS, DRS-UV–visible, and NMR spectroscopy, confirming successful covalent linking

  在这里，我们报告了通过利用胺键合的Zr（IV）金属-有机骨架（UiO-66-NH 2）的后合成修饰，通过脱水偶联通过EOSIN-Y的共价连接，合成了一种新型的非均相光催化剂。通过FT-IR，XRD，BET表面分析，TGA以及TEM，SEM，XPS，DRS-UV-可见和NMR光谱对催化剂进行表征，从而证实了EOSIN-Y与悬垂剂成功进行了共价连接框架中的NH 2功能。修饰后的[受电子邮件保护] 2充当C的简单绿色可见光介导的光催化剂H活化叔胺，产率极高。重要的是，发现掺入染料的非均相光催化剂的活性优于均相光催化剂EOSIN-Y的活性。因此，通过开发这样的光催化剂，可以排除均相催化的分离困难以及有毒EOSIN-Y的环境不利影响。此外，[受电子邮件保护的] 2催化剂可连续循环使用多达10个循环，而活性没有任何重大损失。根据文献报道和实验结果，我们还提出了一个合理的反应机理。
• Preparation of secondary amines from nitriles
  申请人：——

  公开号：US20020128513A1

  公开（公告）日：2002-09-12

  Secondary amines of the formula (II) (X—CH 2 —) 2 NH  (II) where X is a C 1-20 -alkyl, C 2-20 -alkenyl or C 3-8 -cycloalkyl group which may be unsubstituted or substituted by C 1-20 -alkyl, C 3-8 -cycloalkyl, C 4-20 -alkylcycloalkyl, C 4-20 -cycloalkylalkyl, C 2-20 -alkoxyalkyl, C 6-14 -aryl, C 7-20 -alkylaryl, C 7-20 -aralkyl, C 1-20 -alkoxy, hydroxy, C 1-20 -hydroxyalkyl, amino, C 1-20 -alkylamino, C 2-20 -dialkylamino, C 2-12 -alkenylamino, C 3-8 -cycloalkylamino, arylamino, diarylamino, aryl-C 1-8 -alkylamino, halogen, mercapto, C 2-20 -alkenyloxy, C 3-8 -cycloalkoxy, aryloxy and/or C 2-8 -alkoxycarbonyl, are prepared by reacting nitriles of the formula (III) X—CN  (III) with hydrogen at from 20 to 250° C. and pressures of from 60 to 350 bar in the presence of an Rh-containing catalyst comprising from 0.1 to 5% by weight, based on the total weight of the catalyst, of Rh on a support to give mixtures of primary amines of the formula (I) X—CH 2 —NH 2 (I) and secondary amines of the formula (II) (X—CH 2 —) 2 NH  (II) and returning at least part of the primary amines separated from the mixtures obtained to the reaction.

  化学方程式中的次要胺的公式（II）（X—CH2—）2NH  （II），其中X是C1-20-烷基、C2-20-烯基或C3-8-环烷基，可以未取代或被C1-20-烷基、C3-8-环烷基、C4-20-烷基环烷基、C4-20-环烷基烷基、C2-20-烷氧基烷基、C6-14-芳基、C7-20-烷基芳基、C7-20-芳基烷基、C1-20-烷氧基、羟基、C1-20-羟基烷基、氨基、C1-20-烷基氨基、C2-20-二烷基氨基、C2-12-烯基氨基、C3-8-环烷基氨基、芳基氨基、二芳基胺基、芳基-C1-8-烷基氨基、卤素、巯基、C2-20-烯氧基、C3-8-环烷氧基、芳氧基和/或C2-8-烷氧羰基，通过在20至250°C和60至350巴的压力下，在含有0.1至5%重量Rh的催化剂的存在下，将公式（III）X—CN  （III）的腈与氢反应制备而成，所述催化剂基于总重量的0.1至5%的Rh载于载体上，以给出公式（I）X—CH2—NH2（I）的一次胺和公式（II）（X—CH2—）2NH  （II）的二次胺的混合物，并将至少从所得混合物中分离的一部分一次胺返回反应中。
• Iron-catalysed sequential reaction towards α-aminonitriles from secondary amines, primary alcohols and trimethylsilyl cyanide
  作者：Hang Shen、Liangzhen Hu、Qing Liu、Muhammad Ijaz Hussain、Jing Pan、Mingming Huang、Yan Xiong

  DOI：10.1039/c5cc10346k

  日期：——

  An iron-catalyzed sequential reaction of secondary amines with primary alcohols, trimethylsilyl cyanide and TBHP under mild reaction conditions to afford corresponding [small alpha]-aminonitriles in one-pot was developed for the first time

  首次开发了铁胺催化的仲胺与伯醇，三甲基甲硅烷基氰化物和TBHP在温和的反应条件下进行的顺序反应，一次即可得到相应的α-氨基腈
• Dental composites based on X-ray-opaque mixed oxides prepared by flame spraying
  申请人：Burtscher Peter

  公开号：US20050176843A1

  公开（公告）日：2005-08-11

  The present invention relates to dental composites comprising at least one nanoparticulate mixed oxide (a) of SiO 2 with X-ray-opaque metal oxides of one or more elements selected from the group consisting of Y, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu which has been prepared by flame spraying.

  本发明涉及牙科复合材料，其包括至少一种由火焰喷涂制备的纳米混合氧化物（a）SiO2和选自Y、La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Ho、Er、Tm、Yb、Lu等元素的X射线不透明金属氧化物混合而成的材料。