(S,S)-3,3-二甲基-2-(1-苯基乙胺基)丁腈 | 75158-10-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (S,S)-3,3-二甲基-2-(1-苯基乙胺基)丁腈
• 英文名称: (S,S)-3,3-dimethyl-2-(1-phenylethylamino)butyronitrile
• 英文别名: (2S)-3,3-dimethyl-2-[[(1S)-1-phenylethyl]amino]butanenitrile
• CAS: 75158-10-0
• 化学式: C₁₄H₂₀N₂
• 分子量: 216.326
• InChiKey: GTKIFEDYSFURFE-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (S,S)-3,3-二甲基-2-(1-苯基乙胺基)丁腈 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 作用下， 以 乙醇 为溶剂， 25.0~100.0 ℃ 、303.98 kPa 条件下， 反应 48.0h， 生成 (2S)-2-氨基-3,3-二甲基丁酸甲酯
  参考文献：
  名称：

  Molecular structure of a chiral 3,5-bridged pyridine and the effect of structure on circular dichroic spectra

  摘要：

  DOI：

  10.1021/jo00266a012
• 作为产物：
  描述：

  (R,S)-3,3-dimethyl-2-(1-phenylethylamino)butyronitrile 以 甲醇 为溶剂， 生成 (S,S)-3,3-二甲基-2-(1-苯基乙胺基)丁腈
  参考文献：
  名称：

  Synthesis of new ferrocenyl aminoalcohols and aminonitriles and catalytic properties of the aminoalcohols in the ethylation of benzaldehyde

  摘要：

  Chiral ferrocenyl aminoalcohols possessing either OH or NR2 functionality alpha to the ferrocenyl ring were prepared and exhibit modest enantioselectivities for the addition of diethylzinc to benzaldehyde. Chiral ferrocenyl aminonitriles exhibit a facile inversion process in protonic solvents. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00478-9

文献信息

• Iodine as a novel and efficient reagent for the synthesis of α-aminonitriles by a three-component condensation of carbonyl compounds, amines, and trimethylsilyl cyanide
  作者：Laurel Royer、Surya K. De、Richard A. Gibbs

  DOI：10.1016/j.tetlet.2005.05.005

  日期：2005.7

  A straightforward and general method has been developed for the synthesis of α-aminonitriles by simply combining aldehydes or ketones, amines, and trimethylsilyl cyanides in the presence of a catalytic amount of molecular iodine at room temperature.

  通过在室温下在催化量的分子碘的存在下，简单地将醛或酮，胺和三甲基甲硅烷基氰化物结合起来，已经开发出一种简单而通用的合成α-氨基腈的方法。
• Lithium perchlorate/ diethylether catalyzed aminocyanation of aldehydes
  作者：Akbar Heydari、Parinaz Fatemi、Abdol-Ali Alizadeh

  DOI：10.1016/s0040-4039(98)00354-2

  日期：1998.5

  A simple and efficient one-pot method was developed to give α-aminonitriles from aldehydes + amines + TMSCN in LPDE. Optically active α-aminonitriles were snythesized by using (S)-(−)- or (R)-(+) α-methylbenzylamine, (S)-(−) α-methylbenzylamine affords predominantly S-aminonitriles and (R)-(+) α-methylbenzylamine leads to the R-aminonitriles.

  开发了一种简单有效的一锅法，由LPDE中的醛+胺+ TMSCN生成α-氨基腈。通过使用（S）-（-）-或（R）-（+）α-甲基苄胺来合成旋光性α-氨基腈，（S）-（-）α-甲基苄胺主要提供S-氨基腈和（R）-（ +）α-甲基苄胺导致R-氨基腈。
• Asymmetric Strecker Reaction with Chiral Amines: a Catalyst-Free Protocol Using Acetone Cyanohydrin in Water
  作者：Matteo Pori、Paola Galletti、Roberto Soldati、Daria Giacomini

  DOI：10.1002/ejoc.201201533

  日期：2013.3

  The synthesis of a series of new chiral α-aminonitriles was achieved in a diastereoselective Strecker reaction in a one-pot procedure with aldehydes, enantiopure amines, and acetone cyanohydrin in water. Primary and secondary amines derived from L-α-amino acids were used as sources of chirality. The reactions proceeded efficiently without any catalyst at room temperature. The diastereoselectivity of

  一系列新的手性 α-氨基腈的合成是在非对映选择性 Strecker 反应中与醛、对映纯胺和丙酮氰醇在水中的单锅程序中合成的。源自 L-α-氨基酸的伯胺和仲胺用作手性来源。反应在室温下在没有任何催化剂的情况下有效进行。研究了该过程的非对映选择性和新手性 α-氨基腈的构型稳定性。报告了通过 NMR 分析鉴定不稳定中间体，并报告了不对称诱导的拟议机制和模型。据报道，脯氨酸衍生的手性 α-氨基腈化学转化为手性氨基二酸、氨基和酰胺。
• 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.