4-[(苄基)氨基]丁腈 | 71510-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(苄基)氨基]丁腈
• 中文别名: 4-[[4-(叔-丁基)苯氧基]甲基]-5-硝基藜芦醚
• 英文名称: N-(3-cyanopropyl)benzylamine
• 英文别名: 4-(Benzylamino)-butyronitril；4-(benzylamino)butanenitrile；4-benzylaminobutyronitrile；4-Benzylamino-butyronitril；4-Benzylaminobutyronitril
• CAS: 71510-64-0
• 化学式: C₁₁H₁₄N₂
• mdl: MFCD11150637
• 分子量: 174.246
• InChiKey: NZJWITSLFKTATC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 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：

  4-[(苄基)氨基]丁腈 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-苄基丁二胺
  参考文献：
  名称：

  α，ω-二取代Alkanen中的Masseuspektrometrische Zerfallsreaktionen。15.卫生法或医疗法[1] †

  摘要：

  研究了α，ω-二取代烷烃的质谱行为，尤其是不同的N-取代的α，ω-二氨基烷烃的质谱行为。发现被CH 2-基团隔开的两个氨基只能在很小的程度上彼此独立地断裂。然而，这些断裂反应主要是两个官能团都参与其中。这种类型的主要反应是：

  DOI：

  10.1002/hlca.19710540224
• 作为产物：
  描述：

  2-(benzylideneamino)cyclopropanecarbonitrile 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以47%的产率得到4-[(苄基)氨基]丁腈
  参考文献：
  名称：

  Synthesis of 2-[(Arylmethylene)amino]cyclopropanecarbonitriles via a Two-Step Ring Transformation of 2-(Cyanomethyl)aziridines

  摘要：

  2-(氰基甲基)氮杂环丁烯与N-溴琥珀酰亚胺在二氯甲烷中的反应生成高收率的3-[(芳烯基)氨基]-4-溴丁腈。后者的β-氨基-γ-溴丁腈通过与醋酸钾的反应进行1,3-环化，转化为可分离的反式和顺式2-[(芳烯基)氨基]环丙烷碳腈，从而完成了2-(氰基甲基)氮杂环丁烯到2-[(芳烯基)氨基]环丙烷碳腈的两步环转化。

  DOI：

  10.1055/s-0028-1088000

文献信息

• Acylhydrocarbylaminoalkanoic acids, compositions and uses
  申请人：Byk Gulden Lomberg Chemische Fabrik GmbH

  公开号：US04243678A1

  公开（公告）日：1981-01-06

  Compounds of the formula ##STR1## wherein R is (a) optionally-substituted and optionally-hydrogenated biphenylyl, (b) optionally-substituted and optionally-hydrogenated bicyclic aryl having from 8 to 12 ring carbon atoms or (c) a radical of the formula ##STR2## R.sup.1 is aliphatic hydrocarbyl, alicyclic hydrocarbyl or optionally-substituted phenyl; R.sup.2 is --H or lower aliphatic hydrocarbyl; R.sup.3 is --H, lower alkyl, cycloalkyl, optionally-substituted phenyl or, with R.sup.4, alkylene; R.sup.4 is lower alkyl, cycloalkyl, optionally-substituted phenyl, optionally-(nuclearly)-substituted phenalkyl or, with R.sup.3, alkylene; or R.sup.2,R.sup.3 and R.sup.4, together with the carbon to which each is bound, are adamantyl; and n is 3, 4 or 5; and salts thereof with a base are pharmacologically active. Esters thereof are valuable intermediates for the preparation of the pharmacologically-active compounds. Physiologically-acceptable embodiments are administered, e.g., in the form of an appropriate pharmaceutical composition to warm-blooded animals for protection against and treatment for stomach, intestine, pancreas, bile and liver disorders. Syntheses of pharmacologically-active components, transforming toxic embodiments to physiologically-acceptable principles, compounding such principles into pharmaceutical compositions and using such principles for preventing and treating the noted disorders are discussed.

  该公式化合物的化合物##STR1##其中R是(a)选择性取代和选择性氢化的联苯基，(b)选择性取代和选择性氢化的含有8至12个环碳原子的双环芳基，或(c)具有式##STR2##的基团R.sup.1是脂肪烃基，脂环烃基或选择性取代苯基；R.sup.2是--H或较低的脂肪烃基；R.sup.3是--H，较低的烷基，环烷基，选择性取代苯基或与R.sup.4一起，烷基；R.sup.4是较低的烷基，环烷基，选择性取代苯基，选择性-(核)-取代苯基或与R.sup.3一起，烷基；或R.sup.2，R.sup.3和R.sup.4，与每个结合的碳一起，是三环戊烷基；n为3、4或5；及其与碱的盐具有药理活性。其酯是制备具有药理活性的化合物的有价值的中间体。生理可接受的实施例被施用，例如，以适当的药物组合的形式给温血动物，用于预防和治疗胃、肠、胰腺、胆汁和肝脏疾病。讨论了药理活性成分的合成，将有毒实施例转化为生理可接受的原则，将这些原则混合成药物组合物，并将这些原则用于预防和治疗上述疾病。
• Copper-Catalyzed Cyanoalkylation of Amines via C–C Bond Cleavage: An Approach for C(sp³)–N Bond Formations
  作者：Lin Yang、Jia-Yu Zhang、Xin-Hua Duan、Pin Gao、Jiao Jiao、Li-Na Guo

  DOI：10.1021/acs.joc.9b01084

  日期：2019.7.5

  The efficient copper-catalyzed cyanoalkylation of amines via C–C bond cleavage has been demonstrated. Distinctive features of this procedure involves mild conditions, broad range of nitrogen nucleophiles, high selectivity, and good functional group tolerance, thus providing a useful approach for the C(sp3)–N bond formations. Most importantly, this protocol is applicable to the late-stage functionalization

  已经证明了通过C–C键裂解的铜的高效胺催化氰基烷基化反应。此过程的显着特征涉及温和条件，宽范围的氮亲核试剂，高选择性和良好的官能团耐受性，因此为形成C（sp 3）–N键提供了一种有用的方法。最重要的是，该协议适用于天然产物，氨基酸酯和药物的后期功能化。机理研究表明，自由基中间体参与了这一转变。
• Central Cholinergic Agents. I. Potent Acethlcholinesterase Inhibitors, 2-(.OMEGA.-(N-Alkyl-N-(.OMEGA.-phenyl-alkyl)amino)alkyl)-1H-isoindole-1,3(2H)-diones, Based on a New Hypothesis of the Enzyme's Active Site.
  作者：Yuji ISHIHARA、Koki KATO、Giichi GOTO

  DOI：10.1248/cpb.39.3225

  日期：——

  It has been suggested that the active site of acetylcholinesterase contains a hydrophobic binding site (HBS-1), which is closely adjacent to both the anionic and the esteratic sites. In this paper, we assumed that there exists another hydrophobic binding site (HBS-2), some distance removed from the anionic site. On this assumption, a new working hypothesis was proposed for the design of acetylcholinesterase inhibitors. A series of 2-[ω-[N-alkyl-N-(ω-phenyl-alkyl)amino]alkyl]-1H-isoindole-1, 3(2H)-diones was designed based on this hypothesis and tested for its inhibitory activities on acetylcholinesterase. Some in this series were revealed to be more potent than physostigmine. Optimum activity was found to be associated with a five carbon chain length separating the benzylamino group from the 1H-isoindole-1, 3(2H)-dione (phthalimide) moiety. Quantitative study of substitution effect on the phthalimide moiety revealed that hydrophilic and electron-withdrawing groups enhance the activity.

  有人提出，乙酰胆碱酯酶的活性部位包含一个疏水性结合位点(HBS-1)，该位点紧邻阴离子位点和酯酶位点。本文假设存在另一个疏水性结合位点(HBS-2)，该位点与阴离子位点相距一定距离。基于此假设，我们提出了设计新型乙酰胆碱酯酶抑制剂的工作假说。依据该假说，设计了一系列2-[ω-[N-烷基-N-(ω-苯基-烷基)氨基]烷基]-1H-异吲哚-1,3(2H)-二酮，并测试了它们对乙酰胆碱酯酶的抑制活性。系列中某些化合物的抑制活性显示出比毒扁豆碱更强的效力。最佳活性与苄氨基与1H-异吲哚-1,3(2H)-二酮(邻苯二甲酰亚胺)部分之间间隔五个碳原子相关。对邻苯二甲酰亚胺部分进行取代效应的定量研究发现，亲水性和吸电子基团能提高活性。
• Synthesis of 1,6-Disubstituted 4,5,6,7-Tetrahydropyrazolo[3,4-c]pyridin-7-one Derivatives and Evaluation of Their Anticancer Activity
  作者：Vani Nelamane Devegowda、Seon-Hee Seo、Ae Nim Pae、Ghil-Soo Nam、Kyung-Il Choi

  DOI：10.5012/bkcs.2012.33.2.647

  日期：2012.2.20

  Promising anticancer compounds of the type 1,6-disubstituted 4,5,6,7-tetrahydropyrazolo[3,4-c]pyridin-7-ones were identified. The target compounds were readily synthesized in a large scale via a sequence of reactions starting from the commercially available primary amines. Their in vitro anti-proliferative activity has been evaluated on prostate (DU-145), colon (HT-29 and HCT-116) and melanoma (A375P) human cancer cell lines. The relationships between the structure and the anticancer activity, covering all tested cancer cell lines, revealed that the compound 5c with 2,4-dimethylphenyl substituent at $R^2$ was the most potent with the $IC_50}$ values in the range as low as 0.16 to $0.40\mu}M$.

  发现了有前景的抗癌化合物，类型为1,6-二取代的4,5,6,7-四氢吡咯并[3,4-c]吡啶-7-酮。这些靶化合物通过一系列反应，从商业可获得的初级胺出发，容易大规模合成。它们在前列腺（DU-145）、结肠（HT-29和HCT-116）以及黑色素瘤（A375P）的人癌细胞系上进行了体外抗增殖活性评估。结构与抗癌活性之间的关系覆盖了所有测试的癌细胞系，结果显示，化合物5c在处具有2,4-二甲基苯取代基，是最有效的，其值低至0.16至<0.40\mu}M>。
• NOVEL 1,6-DISUBSTITUTED-3-AMINO-4,5,6,7-TETRAHYDRO-1H-PYRAZOLO[3,4-C]PYRIDIN-7-ONE COMPOUNDS AND PREPARATION THEREOF
  申请人：NAM Ghilsoo

  公开号：US20110319619A1

  公开（公告）日：2011-12-29

  Provided are a novel 1,6-disubstituted-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-7-one compound, a pharmaceutically acceptable salt compound thereof, a method for preparing the compound, and an anticancer pharmaceutical composition including the compound as an effective ingredient.

  提供了一种新颖的1,6-二取代-4,5,6,7-四氢-1H-吡唑并[3,4-c]吡啶-7-酮化合物，其药用盐化合物，一种制备该化合物的方法，以及包含该化合物作为有效成分的抗癌药物组合物。