(dicyclopropylmethylene)amine | 93680-23-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (dicyclopropylmethylene)amine
• 英文别名: dicyclopropylketimine；Dicyclopropylmethanimine
• CAS: 93680-23-0
• 化学式: C₇H₁₁N
• 分子量: 109.171
• InChiKey: FOMOUHOLMFMUIK-UHFFFAOYSA-N

物化性质

• 沸点：
  228.6±7.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  23.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (dicyclopropylmethylene)amine 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 0.33h， 生成 dicyclopropylmethanimine hydrochloride
  参考文献：
  名称：

  Syntheses and Reactions of Some Cyclopropyl-substituted Imines. Part 2. Structural and Conformational Properties of Dicyclopropylketimine as Studied by Microwave Spectroscopy and Quantum Chemical Calculations.

  摘要：

  DOI：

  10.3891/acta.chem.scand.53-0291
• 作为产物：
  描述：

  双环丙基酮 在 1,3-二甲基-2-咪唑啉酮 、 四丁基氟化铵 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以95%的产率得到(dicyclopropylmethylene)amine
  参考文献：
  名称：

  原位生成N-未取代酮亚胺一锅催化合成α-四取代氨基酸衍生物

  摘要：

  报道了通过原位产生N-未取代的酮亚胺的α-四取代氨基酸衍生物的一锅催化合成。由于N-未取代的酮亚胺的不可逆形成，产率高于常规一锅法反应条件下产生的产率。该方法无需分离具有烷基取代基的不稳定N-未取代的酮亚胺，并简化了高度拥挤的 α-氨基酸衍生物的合成。

  DOI：

  10.1021/acs.orglett.2c02587

文献信息

• Development of Novel Catalytic Direct Syntheses of N-Unsubstituted Ketimines and Their Applications to One-Pot Reactions
  作者：Hiroyuki Morimoto、Takashi Ohshima、Yuta Kondo

  DOI：10.1055/a-2131-3448

  日期：2024.3

  Herein, we summarize our recent efforts toward developing catalytic methods for the synthesis of N-unsubstituted ketimines and their applications to one-pot reactions for producing various nitrogen-containing compounds. This account provides detailed background, optimization, scope, and mechanistic information. We hope this work will stimulate future studies on the implementation of N-unsubstituted

  在此，我们总结了我们最近在开发合成 N-未取代酮亚胺的催化方法及其在生产各种含氮化合物的一锅反应中的应用的努力。该帐户提供了详细的背景、优化、范围和机制信息。我们希望这项工作能够促进未来对 N-未取代酮亚胺的研究。 1 简介 2 钪催化N-未取代酮亚胺的合成 3 四正丁基氟化铵催化N-未取代酮亚胺的合成 4。结论
• 1-Azoniabicyclo[3.3.0]oct-1(5)-ene salt derivatives and process for the preparation of the same
  申请人：SANWA KAGAKU KENKYUSHO CO., LTD.

  公开号：EP0484702A1

  公开（公告）日：1992-05-13

  There are described 1-azoniabicyclo[3.3.0]oct-1(5)-ene salt derivatives of formula (I) inclusive of 1-azonia-4,6-dimethylbicyclo[3.3.0]oct-1 (5)-ene perchlorate, and a process for the preparation of the same. The derivatives can be prepared by heating dicyclopropylmethanimine salt derivative in a solvent, in the presence or absence of an ammonium salt. Each of the derivatives is employed as an intermediate for preparing various medicines and agricultural chemicals.

  描述了包括 1-氮杂-4,6-二甲基双环[3.3.0]辛-1(5)-烯高氯酸盐在内的式(I)的 1-氮杂双环[3.3.0]辛-1(5)-烯盐衍生物及其制备方法。这些衍生物可以通过在溶剂中加热二环丙基甲亚胺盐衍生物，在有或没有铵盐的情况下制备。每种衍生物都可用作制备各种药物和农药的中间体。
• Syntheses and Reactions of Some Cyclopropyl-Substituted Imines. Part 1.
  作者：Pål Songe、Per Kolsaker、Christian Rømming、Margareta Törnqvist、Yngve Stenstrøm、Ruo-Hua Zhang、Kurt V. Mikkelsen、Alexander Senning

  DOI：10.3891/acta.chem.scand.52-0790

  日期：——

  Quenching the reaction solution from cyclopropanecarbonitrile and cyclopropylmagnesium bromide in tetrahydrofuran (THF) with anhydrous NH3 gave an about equimolar mixture of dicyclopropyl ketimine (3) and 1,1-dicyclopropane-carboximidoylcyclopropane (4). Reactions of the ketimines 3 and 4 with some nucleophiles are described. Thus, reaction of 4 with malononitrile gave a good yield of 2-amino-3-cyano-5-(3,3-dicyanopropyl)-4,6-dicyclopropylpyridine (6). Neat 4, catalysed by MgCl2, gave a self-condensation product, 1,3,5,7-tetracyclopropyl-2,6,9-triazadispirobicyclo[3.3.1]nona-2,6-diene-4,1':8,1 "-dicyclopropane} (7), while an equimolar mixture of neat 3 and 4 with catalytic amounts of MgCl2 gave a mixed condensation product, 2',2',4',6',-tetracyclopropylspiro[cyclopropyl-1 ,5'-(1',5'-dihydropyrimidine)] (8). Hydrolysis of 4 at medium pH gave a mixture of 7 and the partly hydrolysed 4: 1-cyclopropanecarbonyl-1-cyclopropanecarboximidoylcyclopropane (10). Reaction of 3 with cyclopropylamine gave N-cyclopropyldicyclopropyl ketimine (11). Gas phase FTIR-spectra of 4 and 10 indicated intramolecular hydrogen bonds. The structures of 7 and 8 were established by single-crystal X-ray analyses. In the bicyclic compound 7 the apical nitrogen atom is pyramidal, making the structure asymmetric (both enantiomers present in the unit cell), as confirmed by solid-state C-13 NMR spectroscopy. On the other hand solution C-13 NMR shows a high degree of symmetry, explainable by rapid inversion at the apical nitrogen atom.
• Funke, Frank; Duetsch, Michael; Stein, Frank, Chemische Berichte, 1994, vol. 127, # 5, p. 911 - 920
  作者：Funke, Frank、Duetsch, Michael、Stein, Frank、Noltemeyer, Matthias、Meijere, Armin de

  DOI：——

  日期：——
• 7-SUBSTITUIERTE 1-ARYL-NAPHTHYRIDIN-3-CARBONSÄUREAMIDE UND IHRE VERWENDUNG
  申请人：Bayer Aktiengesellschaft

  公开号：EP3512849A1

  公开（公告）日：2019-07-24