1-(cyclohex-1-en-1-yl)ethan-1-amine | 325490-26-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(cyclohex-1-en-1-yl)ethan-1-amine
• 英文别名: 1-(cyclohex-1-en-1-yl)ethanamine；1-(1-cyclohexenyl)ethylamine；1-(cyclohexen-1-yl)ethanamine
• CAS: 325490-26-4
• 化学式: C₈H₁₅N
• 分子量: 125.214
• InChiKey: DYOAYILVQKBJOT-UHFFFAOYSA-N

物化性质

• 沸点：
  72 °C(Press: 11 Torr)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(cyclohex-1-en-1-yl)ethan-1-amine 生成 (S)-1-(1-cyclohexenyl)ethylamine
  参考文献：
  名称：

  Resolution of β-unsaturated amines with isopropylidene glycerol hydrogen phthalate

  摘要：

  1-Phenyl-2-propenylamine 2, 1-phenyl-2-propinylamine 3, 1-(1-cyclohexenyl)ethylamine 4, (E)-2-ethylidenecyclohexylamine 5 and alpha -methylallylamine hydrochloride 6 were selected as candidates for resolution with isopropylidene glycerol hydrogen phthalate 1, previously described as an efficient resolving agent of 1-arylalkylamines. With only the exception of 5, all these substrates were resolved by (S)-1. In particular both the enantiomers of 2 and 3 were obtained in excellent yields and with very high enantiomeric excesses. The absolute configurations of non-racemic forms of 2, 3 and 4, not prepared before except those of 3, were established by correlation with the respective hydrogenation products. The enantiomeric excesses of all the resolved substrates were accurately determined by chiral HPLC analysis. The fact that 1 resolves 4 and 6 but not their saturated analogues and shows higher efficiency in resolving 2 and 3 than 1-phenylpropylamine indicates the positive influence of the presence of beta -unsaturation on the resolvability of aminic substrates with such an acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00373-6
• 作为产物：
  描述：

  亚乙基环己烷 在 溶剂黄146 、 锌 作用下， 以 丙酮 、 苯 为溶剂， 反应 19.25h， 生成 1-(cyclohex-1-en-1-yl)ethan-1-amine
  参考文献：
  名称：

  Amination of olefinic compounds with bis(2,2,2-trichloroethyl) azodicarboxylate

  摘要：

  DOI：

  10.1021/jo00005a063

文献信息

• Non-enzymatic acylative kinetic resolution of primary allylic amines
  作者：Amandine Kolleth、Martin Cattoen、Stellios Arseniyadis、Janine Cossy

  DOI：10.1039/c3cc45453c

  日期：——

  A non-enzymatic acetyl transfer-based kinetic resolution of primary allylic amines is reported. The process involves the use of (1S,2S)-1 in conjunction with a supported ammonium salt and affords the corresponding enantio-enriched N-acetylated allylic amines with unprecedented levels of selectivity (s-factors up to 34).

  报道了一种非酶催化的基于乙酰转移的初级烯丙基胺的动力学分离方法。该过程涉及使用(1S,2S)-1与一种支持型铵盐结合，能够以前所未有的选择性（s因子高达34）获得相应的对映体富集的N-乙酰化烯丙基胺。
• Ruthenium-Catalyzed Oxidative Coupling of Primary Amines with Internal Alkynes through CH Bond Activation: Scope and Mechanistic Studies
  作者：Sara Ruiz、Pedro Villuendas、Manuel A. Ortuño、Agustí Lledós、Esteban P. Urriolabeitia

  DOI：10.1002/chem.201500338

  日期：2015.6.1

  presented as a general atom‐economy methodology with a broad scope of applications in the synthesis of N‐heterocycles. Reactions proceed through regioselective CH bond activation in 15 minutes under microwave irradiation or in 24 hours with conventional heating. The synthesis of 2,3,5‐substituted pyridines, benzo[h]isoquinolines, benzo[g]isoquinolines, 8,9‐dihydro‐benzo[de]quinoline, 5,6,7,8‐tetrahydroisoquinolines

  Ru配合物催化伯胺与内部炔烃的氧化偶联是一种通用的原子经济学方法，在N杂环的合成中具有广泛的应用范围。反应通过微波辐射在15分钟内或在常规加热条件下的24小时内通过区域选择性CH键活化而进行。2,3,5-取代的吡啶，苯并[ h ]异喹啉，苯并[ g ]异喹啉，8,9-二氢-苯并[ de ]喹啉，5​​,6,7,8-四氢异喹啉，吡啶基[3， 4克]异喹啉和吡啶[4,3克取决于所用的起始伯胺，可以达到]异喹啉。在苄胺底物上的DFT计算支持了一种反应机理，该机理包括乙酸盐辅助的CH键活化，迁移插入和CN键形成步骤，涉及28–30 kcal mol -1。计算研究扩展到其他底物，即1-萘甲基，2-甲基烯丙基和2-噻吩甲胺。
• Prost,M. et al., Chimica Therapeutica, 1967, vol. 2, p. 133 - 143
  作者：Prost,M. et al.

  DOI：——

  日期：——
• A Dual-Catalysis/Anion-Binding Approach to the Kinetic Resolution of Allylic Amines
  作者：Eric G. Klauber、Nisha Mittal、Tejas K. Shah、Daniel Seidel

  DOI：10.1021/ol200712b

  日期：2011.5.6

  A dual-catalysis approach enables the small-molecule catalyzed kinetic resolution of allylic amines by acylation. By employing 2 mol % of each 4-(pyrrolidin D)pyridine (PPY) and a readily available chiral hydrogen-bonding cocatalyst, the first nonenzymatic kinetic resolution of allylic amines was accomplished with s factors of up to 20.
• EP0986384A4
  申请人：——

  公开号：EP0986384A4

  公开（公告）日：2004-09-15