2-氨基-1-环己烯甲腈 | 15595-71-8

• 物质功能分类: 化学试剂 - 有机试剂 - 氰化物/腈
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-氨基-1-环己烯甲腈
• 英文名称: 2-aminocyclohex-1-enecarbonitrile
• 英文别名: 2-Aminocyclohex-1-ene-1-carbonitrile；2-amino-1-cyclohexene-1-carbonitrile；2-amino-cyclohex-2-ene carbonitrile；1-amino-2-cyanocyclohexene；2-amino-1-cyano-1-cyclohexene；2-aminocyclohexene-1-carbonitrile
• CAS: 15595-71-8
• 化学式: C₇H₁₀N₂
• mdl: MFCD16046430
• 分子量: 122.17
• InChiKey: PFIVIEDNXASHEY-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  326.9±42.0 °C(Predicted)
• 密度：
  1.05±0.1 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：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2-氨基-1-环己烯甲腈 在 硫酸 作用下， 生成 2-氧代环己烷甲腈
  参考文献：
  名称：

  Preparation of Enantiopure Ketones and Alcohols Containing a Quaternary Stereocenter through Parallel Kinetic Resolution of β-Keto Nitriles

  摘要：

  Racemic 1-methyl-2-oxocycloalkanecarbonitriles have been subjected to bioreduction by the fungus Mortierella isabellina NRRL 1757 through a parallel kinetic-resolution process. The u and l alcohols thus obtained (up to >99% ee) were easily separated and oxidized to the R and S ketones, respectively. The process can be then repeated so that both enantiomers of the ketone and two epimers of the alcohol can be obtained in their enantiopure forms.

  DOI：

  10.1021/jo011092t
• 作为产物：
  描述：

  2-氧代环己烷甲腈 在 ammonium carbonate 作用下， 生成 2-氨基-1-环己烯甲腈
  参考文献：
  名称：

  v. Auwers; Bahr; Frese, Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 67

  摘要：

  DOI：

文献信息

• Diverse Tandem Cyclization Reactions of <i>o</i>-Cyanoanilines and Diaryliodonium Salts with Copper Catalyst for the Construction of Quinazolinimine and Acridine Scaffolds
  作者：Xinlong Pang、Chao Chen、Xiang Su、Ming Li、Lirong Wen

  DOI：10.1021/ol503156g

  日期：2014.12.5

  Two cyclization modes are realized to produce different nitrogen-containing heterocycles, i.e., quinazolin-4(3H)-imines and acridines by assembling o-cyanoanilines and diaryliodonium salts via tandem reaction pathways.

  通过经由串联反应途径组装邻氰基苯胺和二芳基碘鎓盐，实现了两种环化模式以产生不同的含氮杂环，即喹唑啉-4（3 H）-亚胺和a啶。
• Certain 9-amino-2-(or 4)-oxa 1,2,3,4-tetrahydro- or
  申请人：Pfizer Inc.

  公开号：US05202440A1

  公开（公告）日：1993-04-13

  Compounds selected from the group consisting of 9-amino-4-oxa-1,2,3,4-tetrahydro-acridine, 9-amino-2-oxa-1,2,3,4-tetrahydro-acridine, 9-amino-8-fluoro-4-oxa-1,2,3,4-tetrahydro-acridine, 9-amino-4-oxa-1,2,3,4,5,6,7,8-octahydro-acridine or a pharmaceutical acceptable salt thereof are useful treating Alzheimer's disease.

  从由9-氨基-4-氧杂-1,2,3,4-四氢吖啶、9-氨基-2-氧杂-1,2,3,4-四氢吖啶、9-氨基-8-氟-4-氧杂-1,2,3,4-四氢吖啶、9-氨基-4-氧杂-1,2,3,4,5,6,7,8-八氢吖啶或其药物可接受盐组成的组中选出的化合物，用于治疗阿尔茨海默病是有用的。
• Tin (IV) chloride-promoted reactions of β-dicarbonyl compounds with nitriles. Synthesis of aminopyridines and aminoquinolines.
  作者：Augusto C. Veronese、Rosella Callegari、Suada Ahmed Ali Salah

  DOI：10.1016/s0040-4039(00)97429-x

  日期：1990.1

  β-Ketoesters and β-diesters react with β-enaminonitriles in the presence of stoichiometric amounts of tin (IV) chloride to give 4-aminopyridines and pyridones while they react with aromatic orthoaminonitriles to give 4-aminoquinolines and quinolones.

  在化学计量的氯化锡（IV）存在下，β-酮酸酯和β-二酯与β-烯腈反应，生成4-氨基吡啶和吡啶酮，而与芳族邻氨基腈反应，生成4-氨基喹啉和喹诺酮。
• Radical Annulation of 2-Cyanoaryl Acrylamides via C═C Double Bond Cleavage: Access to Amino-Substituted 2-Quinolones
  作者：Wen-Jin Xia、Tai-Gang Fan、Zhi-Wei Zhao、Xin Chen、Xiang-Xiang Wang、Ya-Min Li

  DOI：10.1021/acs.orglett.1c02281

  日期：2021.8.6

  2-cyanoaryl acrylamides via C═C double bond cleavage has been developed for facile and efficient access to a broad spectrum of functionalized 4-amino-2-quinolones, which are important N-heterocycles. In this transformation, the solvent THF is demonstrated to play a crucial role, and the addition of alkyl radicals to nitrile, 1,5-hydride shift, and cleavage of the C–C bond are involved in the mechanism

  已经开发了一种通过 C=C 双键裂解的 2-氰基丙烯酰胺的新型环化，以方便有效地获得广泛的官能化 4-氨基-2-喹诺酮类化合物，它们是重要的N-杂环。在这种转化中，溶剂四氢呋喃被证明起着至关重要的作用，烷基与腈的加成、1,5-氢化物转移和 C-C 键的断裂都参与了该机制。
• Catalytic Reductive Synthesis and Direct Derivatization of Unprotected Aminoindoles, Aminopyrroles, and Iminoindolines
  作者：Leonardus H. Leijendekker、Jens Weweler、Tobias M. Leuther、Jan Streuff

  DOI：10.1002/anie.201702310

  日期：2017.5.22

  A titanium(III)-catalyzed radical cyclization to unprotected 3-aminoindoles, 3-aminopyrroles, or 3-iminoindolines is reported. The reaction is non-hazardous, scalable, and allows facile isolation of the free products by extraction. The method is demonstrated on a large substrate scope and it further allows the direct installation of various nitrogen protecting groups or the synthesis of building blocks

  报道了钛（III）催化的自由基环化成未保护的3-氨基吲哚，3-氨基吡咯或3-亚氨基二氢吲哚。该反应是无害的，可扩展的，并且允许通过萃取容易地分离游离产物。该方法在较大的底物范围内得到了证明，它还允许直接安装各种氮保护基团或以单一顺序合成肽化学的基础材料。熔融双吲哚可直接从环化产物中获得。