2-(phenylethylamino)acetonitrile | 3591-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(phenylethylamino)acetonitrile
• 英文别名: [(2-Phenylethyl)amino]acetonitrile；2-(2-phenylethylamino)acetonitrile
• CAS: 3591-82-0
• 化学式: C₁₀H₁₂N₂
• 分子量: 160.219
• InChiKey: XVUYNNMVJLUTMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-(phenylethylamino)acetonitrile 在 甲酸 、 硫酸 、 镍 、 N,N'-二环己基碳二亚胺 作用下， 以 水 为溶剂， 反应 80.5h， 生成 吡喹酮
  参考文献：
  名称：

  A new synthesis 2-acyl-1,2,3,6,7,11b-hexahydropyrazino[2,1-a]isoquinolin-4-ones based on N-cyanomethyl derivatives of 2-phenyl-ethylamides of acylglycines

  摘要：

  DOI：

  10.1007/bf00531659
• 作为产物：
  描述：

  氯乙腈 、 2-苯乙胺 在 三乙胺 作用下， 以91%的产率得到2-(phenylethylamino)acetonitrile
  参考文献：
  名称：

  2-amino-6,7,8,9-tetrahydro-6-phenethyl-3H-pyrimido[4,5-e][1,4]diazepin-4(5H)-one 的合成：潜在嘧啶的模型[4,5-e][1,4]二氮杂类叶酸抗肿瘤剂

  摘要：

  摘要 2-{N-[(2-amino-4,6-dichloropyrimidin-5-yl)methyl]-N-phenethylamino}乙腈 (5) 与 Raney 镍和氢还原环化得到氯嘧啶 [4,5-e ][1,4]二氮杂 3 不能通过尝试用氢氧化物进行亲核芳族取代转化为 2。然而，通过 2-{N-[(2-氨基-4-氯-6-甲氧基嘧啶-5-基)甲基]-N-苯乙氨基}乙腈 (13) 的还原性环化制备标题化合物 (2)然后用三甲基碘硅烷处理。

  DOI：

  10.1515/hc-2015-0216

文献信息

• Structure-affinity relationships of 12-sulfonyl derivatives of 5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquino[2,1-g][1,6]naphthyridines at .alpha.-adrenoceptors
  作者：Robin D. Clark、David B. Repke、Jacob Berger、Janis T. Nelson、Andrew T. Kilpatrick、Christine M. Brown、Alison C. MacKinnon、Ruth U. Clague、Michael Spedding

  DOI：10.1021/jm00106a036

  日期：1991.2

  dependent on the stereochemistry of the tetracyclic system. The 8a beta,12a alpha,13a alpha diastereomer of 1 (56) had moderate affinity for alpha 2-adrenoceptors while the 8a beta,12a beta,13a alpha diastereomer (55) had very low affinity. The affinity and selectivity of these agents for alpha 2-adrenoceptors was found to correspond to that observed for several isomeric yohimbine analogues which have

  有效的α2-肾上腺素受体拮抗剂（8aR，12aS，13aS）-5,8,8a，9,10,11,12,12a，13,13a-十氢-3-甲氧基-12-（甲基磺酰基）-6H的类似物制备了-异喹啉[2,1-g] [1,6]萘啶（1b），并评估了α1-和α2-肾上腺素受体的亲和力。通过从大鼠大脑皮膜中置换[3H]育亨宾来评估对α2肾上腺素受体的亲和力，尽管1b和紧密的结构类似物表现出高亲和力，但对于存在于该组织中的α2A或α2B亚型均没有选择性。然而，所有的高亲和力α2-肾上腺素受体配体对[3 H]吡唑嗪（α1）结合具有选择性。发现对[3 H]育亨宾标记的α2-肾上腺素受体的亲和力高度依赖于四环系统的立体化学。8a beta，12a alpha，1（56）的13a alpha非对映异构体对α2肾上腺素受体具有中等亲和力，而8a beta，12a beta，13a alpha非对映异构体（55）具有非常
• A Novel Transformation of Primary Amines to N-Monoalkylhydroxylamines
  作者：Hidetoshi Tokuyama、Takeshi Kuboyama、Akiko Amano、Tohru Yamashita、Tohru Fukuyama

  DOI：10.1055/s-2000-6428

  日期：——

  A novel transformation of primary amines to the corresponding N-monoalkylhydroxylamines is described. The three-step protocol involves selective mono-cyanomethylation of primary amines, regioselective formation of nitrones by m-CPBA oxidation, and hydroxylaminolysis of the nitrones with hydroxylamine hydrochloride. The method is applicable for a wide range of primary amines, including alkyl, benzyl, and chiral.

  本文介绍了一种将伯胺转化为相应的 N-单烷基羟胺的新方法。该三步法包括伯胺的选择性单氰基甲基化、通过间-氯丙基苯甲酸氧化作用形成具有区域选择性的亚硝基，以及用盐酸羟胺对亚硝基进行羟基氨分解。该方法适用于多种伯胺，包括烷基伯胺、苄基伯胺和手性伯胺。
• Design, Synthesis and Evaluation of Serine Protease Inhibitor Analogues
  作者：Laila Kamoune、Wim M. De Borggraeve、Constant Gielens、Arnout Voet、Koen Robeyns、Marc De Maeyer、Luc Van Meervelt、Frans Compernolle、Georges Hoornaert

  DOI：10.1002/ejoc.200700180

  日期：2007.6

  Recent efforts in the field of thrombin inhibitor research have focused on the identification of pyrazinone-containing compounds. In this manuscript we describe the synthesis of the new pyrazinones 12-36. All the targets were fully characterised and screened for serine protease inhibition. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

  最近凝血酶抑制剂研究领域的努力集中在鉴定含吡嗪酮的化合物上。在这份手稿中，我们描述了新的吡嗪酮 12-36 的合成。所有目标都经过充分表征并筛选丝氨酸蛋白酶抑制。© Wiley-VCH Verlag GmbH & Co. KGaA，2007 年。
• NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES
  申请人：Menet Christel Jeanne Marie

  公开号：US20110190260A1

  公开（公告）日：2011-08-04

  [1,2,4]Triazolo[1,5-a]pyridine compounds are disclosed that have a formula represented by the formula (I). The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diseases involving cartilage degradation, bone and/or joint degradation, for example osteoarthritis; and/or conditions involving inflammation or immune responses, such as Crohn's disease, rheumatoid arthritis, psoriasis, allergic airways disease (e.g. asthma, rhinitis), juvenile idiopathic arthritis, colitis, inflammatory bowel diseases, endotoxin-driven disease states (e.g. complications after bypass surgery or chronic endotoxin states contributing to e.g. chronic cardiac failure), diseases involving impairment of cartilage turnover (e.g diseases involving the anabolic stimulation of chondrocytes), congenital cartilage malformations, diseases associated with hypersecretion of IL6, transplantation rejection (e.g. organ transplant rejection) and proliferative diseases.

  本文披露了一种具有公式（I）所表示的化学式的[1,2,4]三唑并[1,5-a]吡啶化合物。这些化合物可以制备为药物组合物，并可用于预防和治疗哺乳动物（包括人类）的各种疾病，包括但不限于涉及软骨降解、骨骼和/或关节降解的疾病，例如骨关节炎；以及涉及炎症或免疫反应的疾病，如克隆病、类风湿性关节炎、牛皮癣、过敏性呼吸道疾病（例如哮喘、鼻炎）、少年特发性关节炎、结肠炎、炎性肠病、内毒素驱动的疾病状态（例如旁路手术后的并发症或慢性内毒素状态导致的慢性心力衰竭等）、涉及软骨周转障碍的疾病（例如涉及软骨细胞的合成刺激的疾病）、先天性软骨畸形、与IL6高分泌相关的疾病、移植排斥（例如器官移植排斥）和增生性疾病。
• Compounds useful for the treatment of degenerative and inflammatory diseases
  申请人：Menet Christel Jeanne Marie

  公开号：US08853240B2

  公开（公告）日：2014-10-07

  [1,2,4]triazolo[1,5-a]pyridine compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, diseases involving cartilage degradation, bone and/or joint degradation, for example osteoarthritis; and/or conditions involving inflammation or immune responses, such as Crohn's disease, rheumatoid arthritis, psoriasis, allergic airways disease (e.g. asthma, rhinitis), juvenile idiopathic arthritis, colitis, inflammatory bowel diseases, endotoxin-driven disease states (e.g. complications after bypass surgery or chronic endotoxin states contributing to e.g. chronic cardiac failure), diseases involving impairment of cartilage turnover (e.g. diseases involving the anabolic stimulation of chondrocytes), congenital cartilage malformations, diseases associated with hypersecretion of IL6 and transplantation rejection (e.g. organ transplant rejection) and proliferative diseases.

  本文披露了一种公式如下的[1,2,4]三唑并[1,5-a]吡啶化合物：这些化合物可制备为药物组合物，并可用于预防和治疗哺乳动物包括人类的各种疾病，包括但不限于涉及软骨降解、骨骼和/或关节退化的疾病，例如骨关节炎；以及涉及炎症或免疫反应的疾病，例如克罗恩病、类风湿性关节炎、牛皮癣、过敏性呼吸道疾病（例如哮喘、鼻炎）、少年特发性关节炎、结肠炎、炎性肠病、内毒素驱动的疾病状态（例如旁路手术后的并发症或慢性内毒素状态导致的慢性心力衰竭等），涉及软骨周转障碍的疾病（例如涉及软骨细胞的合成刺激的疾病）、先天性软骨畸形、与IL6高分泌相关的疾病和移植排斥（例如器官移植排斥）以及增生性疾病。