1-(phenylamino)cycloheptanecarbonitrile | 92292-01-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(phenylamino)cycloheptanecarbonitrile
• 英文别名: 1-Anilino-1-cyan-cycloheptan；1-Anilino-1-cycloheptane carbonitrile；1-anilinocycloheptane-1-carbonitrile
• CAS: 92292-01-8
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: YAGBCOPLMKDFBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  1-(phenylamino)cycloheptanecarbonitrile 在 乙醇 、 sodium 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 1-Phenyl-3-(1-phenylamino-cycloheptylmethyl)-thiourea
  参考文献：
  名称：

  Studies on Organophosphorus Compounds: The Synthesis of [1,3,2]-Diazaphospholes and [1,3,2]-Oxaazaphospholes

  摘要：

  A number of spiro[cyclopentane (cyclohexane, and cycloheptane)-1,4'-perhydro-[1,3,2]diazaphosphole] derivatives (3a-c, 5a-c, 11a-c, and 12a-c) and spiro-[cyclopentane (cyclohexane, and cycloheptane)-1,4'-perhydro[1,3,2]oxaazaphos-phole] derivatives (7a-c) were prepared via an interaction of 2,4-bis-(4-methoxy-phenyl)-1,3,2,4-dithiaphosphetane-2,4-disulphide (1) with substances containing two functional groups.

  DOI：

  10.1080/10426500600754794
• 作为产物：
  描述：

  三甲基氰硅烷 、 苯胺 、 环庚酮 在 C₂₅H₂₄N₄O₄*2C₁₆H₁₄O₄Si^(2-)*2Zn⁽²⁺⁾*2H₂O 作用下， 以 neat (no solvent) 为溶剂， 反应 5.0h， 生成 1-(phenylamino)cycloheptanecarbonitrile
  参考文献：
  名称：

  微孔金属有机骨架催化剂在环境条件下无溶剂斯特雷克反应和CO 2固定

  摘要：

  乙酸锌（II）四水合物，柔性四吡啶基配体，四（3-吡啶基氧基亚甲基）甲烷（3-tpom），弯曲的二羧酸和4,4'-（二甲基硅烷二基）双苯甲酸（H 2 L）在溶剂热条件下导致形成微孔锌（II）-有机骨架{{Zn 2（3-tpom）（L）2 ]·2H 2 O} n（1）。从热重分析可以明显看出，该框架具有很好的热稳定性，而温度可变粉末X射线衍射分析进一步支持了该框架。通过气体吸附分析已经确定了骨架的微孔性质。与其他在环境条件（298 K和1 bar压力）下具有较大动力学直径（N 2为3.64Å，CH 4为3.8Å ）的气体相比，该框架具有出色的选择性二氧化碳吸附能力。此外，装饰有催化活性不饱和金属位点的骨架是CO 2环加成反应的良好催化剂与环氧化物和三组分Strecker反应在环境条件下进行，不需要任何溶剂。异质性以及在环境和无溶剂条件下的良好催化活性使1作为这些有机转化的优良催化剂。

  DOI：

  10.1021/acs.inorgchem.9b03051

文献信息

• Zr(HSO4)4 catalyzed one-pot strecker synthesis of α-amino nitriles from aldehydes and ketones under solvent-free conditions
  作者：A. R. Hajipour、Y. Ghayeb、N. Sheikhan

  DOI：10.1007/bf03246031

  日期：2010.6

  A mild and efficient method has been developed for the preparation of α-amino nitriles from the condensation of aldehydes and ketones with aniline and TMSCN in the presence of a catalytic amount of Zr(HSO4)4 under solvent-free conditions at room temperature.

  已经开发了一种温和有效的方法，在室温下在无溶剂条件下，在催化量的Zr（HSO 4）4存在下，由醛和酮与苯胺和TMSCN缩合制备α-氨基腈。
• Magnetic Fe3O4–BF3: highly efficient Lewis acid catalyst for the synthesis of α-aminonitriles
  作者：Mohsen Shekouhy、Ali Moaddeli、Ali Khalafi-Nezhad

  DOI：10.1007/s11164-015-2246-4

  日期：2016.4

  magnetically separable Lewis acid catalyst and successfully used for the one-pot synthesis of α -aminonitriles. A broad range of substrates including the aromatic and heteroaromatic aldehydes, cyclic ketones (cyclopentanone, cyclohexanone and cycloheptanone), aryl–alkyl ketones, diaryl ketones and tetralones, isatin derivatives and acenaphthenequinone were condensed with amines (aliphatic and aromatic) and trimethylsilyl

  制备了Fe 3 O 4磁性纳米颗粒负载的BF 3作为新型的可磁分离的路易斯酸催化剂，并成功用于一锅法合成 α- 氨基腈。广泛的底物包括芳族和杂芳族醛，环酮（环戊酮，环己酮和环庚酮），芳基-烷基酮，二芳基酮和四氢萘酮，靛红衍生物和苯醌与胺（脂族和芳族）和三甲基甲硅烷基氰化物缩合。所有反应均在短时间内完成，并以良好至极好的收率获得了产物。该催化剂可以循环使用几次，而不会降低效率。最后， α 含腺嘌呤的-氨基腈已成功合成。
• High pressure mediated three component Strecker synthesis of α-aminonitriles from ketones, aromatic amines and trimethylsilyl cyanide
  作者：Kiyoshi Matsumoto、Jong Chul Kim、Naoto Hayashi、Gérard Jenner

  DOI：10.1016/s0040-4039(02)02270-0

  日期：2002.12

  High pressure (600 MPa) reaction conditions, in the absence of a catalyst, have proved to be a powerful way to stimulate the three component Strecker reaction synthesis of alpha-aminonitriles in high yields. Examples of two types of double Strecker reactions were also described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Application of Secondary Amines in the Synthesis of Some New Spiro Heterocyclic Compounds
  作者：A. M. Soliman、A. A. Sultan、Omran Abd Ellah、A. K. El-Shafei

  DOI：10.1080/10426500802713283

  日期：2010.6.30

  1-Anilinocycloalkanecarbonitriles 1a-c were prepared and reacted with active methylene reagents to give compounds 5a-c through 10a-c and reacted with different other reagents such as benzaldehyde, ethyl aminoacetate, ethyl mercaptoacetate, or hydrazine carbothioamide, which afforded the desired spiro heterocycles compounds 11a-c through 14a-c.
• A novel approach for the synthesis of α-aminonitriles using Mitsunobu’s reagent under solvent-free conditions
  作者：Devdutt Chaturvedi、Amit K. Chaturvedi、Nisha Mishra、Virendra Mishra

  DOI：10.1016/j.tetlet.2012.07.117

  日期：2012.10

  A highly efficient, one-pot, three-component, solvent-free protocol for the synthesis of alpha-aminonitriles starting from their corresponding carbonyl compounds, amines, using Mitsunobu's reagent has been developed. Diversity of alpha-aminonitriles has been synthesized in good to excellent yields (80-99%) using various kinds of aldehydes/ketones and a variety of amines. (C) 2012 Elsevier Ltd. All rights reserved,