(2-氰基乙基氨基)-乙酸甲酯 | 44915-39-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (2-氰基乙基氨基)-乙酸甲酯
• 英文名称: [(2-cyanoethyl)amino]acetic acid methyl ester
• 英文别名: Cyanoethylglycine Methyl Ester；methyl [(2-cyanoethyl)amino]acetate；N-(2-cyano-ethyl)-glycine methyl ester；N-(2-Cyan-aethyl)-glycin-methylester；N-<2-Cyanethyl>-glykokoll-methylester；N-<2-Cyan-ethyl>-glycin-methylester；methyl 2-(2-cyanoethylamino)acetate
• CAS: 44915-39-1
• 化学式: C₆H₁₀N₂O₂
• mdl: MFCD09031159
• 分子量: 142.158
• InChiKey: GWBTUTBQZWQICM-UHFFFAOYSA-N

物化性质

• 沸点：
  142-143 °C(Press: 12 Torr)
• 密度：
  1.0983 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  (2-氰基乙基氨基)-乙酸甲酯 在 盐酸肼 、 sodium methylate 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 32.0h， 生成 3-氨基-5-叔丁氧羰基-吡咯并[3,4-C]吡唑
  参考文献：
  名称：

  Potent and Selective Aurora Inhibitors Identified by the Expansion of a Novel Scaffold for Protein Kinase Inhibition

  摘要：

  Potent and selective Aurora kinase inhibitors were identified from the combinatorial expansion of the 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole bi-cycle, a novel and versatile scaffold designed to target the ATP pocket of protein kinases. The most potent compound reported in this study had an IC(50) of 0.027 microM in the enzymatic assay for Aur-A inhibition and IC(50)s between 0.05 microM and 0.5 microM for the inhibition of proliferation of different tumor cell lines.

  DOI：

  10.1021/jm049076m
• 作为产物：
  描述：

  丙烯腈 、 甘胺酸甲酯 反应 48.0h， 以52.8%的产率得到(2-氰基乙基氨基)-乙酸甲酯
  参考文献：
  名称：

  Negrebetskii, Vad. V.; Kolesova, V. A.; Bobkova, R. G., Journal of general chemistry of the USSR, 1991, vol. 61, # 1.1, p. 104 - 108

  摘要：

  DOI：

文献信息

• [EN] PROCESS FOR THE PREPARATION OF AN alpha-AMINO CARBONYL COMPOUND<br/>[FR] PROCEDE DE PREPARATION D'UN COMPOSE DOLLAR G(A)-AMINO CARBONYLE
  申请人：DSM IP ASSETS BV

  公开号：WO2004078702A1

  公开（公告）日：2004-09-16

  The invention relates to a process for the preparation of an α-amino carbonyl compound by reacting an imine starting material with a suitable electrophile in the presence of a base. This process has the advantage that the imine starting materials can be prepared from glyoxylic acid esters or glyoxylic acid ester derivatives and α-hydrogen containing primary amines, which are usually cheap and readily available. These imine starting materials can usually be prepared with a high yield and/or almost without the formation of any side products.

  该发明涉及一种通过在碱存在下，将亚胺起始物与适当的亲电试剂反应制备α-氨基羰基化合物的方法。这种方法的优点在于，亚胺起始物可以由乙酰乙酸酯或乙酰乙酸酯衍生物和α-氢含量的一级胺反应制备，这些原料通常便宜且易得。这些亚胺起始物通常可以高产率地制备，或几乎不形成任何副产物。
• Process for the preparation of an alpha-amino carbonyl compound
  申请人：Hyett John David

  公开号：US20060135790A1

  公开（公告）日：2006-06-22

  The invention relates to a process for the preparation of an α-amino carbonyl compound by reacting an imine starting material with a suitable electrophile in the presence of a base. This process has the advantage that the imine starting materials can be prepared from glyoxylic acid esters or glyoxylic acid ester derivatives and α-hydrogen containing primary amines, which are usually cheap and readily available. These imine starting materials can usually be prepared with a high yield and/or almost without the formation of any side products.

  本发明涉及一种α-氨基羰基化合物的制备工艺，该工艺通过亚胺起始原料与合适的亲电子体在碱存在下发生反应来制备α-氨基羰基化合物。这种工艺的优点是，亚胺起始原料可以从乙醛酸酯或乙醛酸酯衍生物和含α-氢的伯胺中制备，这些原料通常便宜且容易获得。这些亚胺起始原料通常可以高产和/或几乎不产生任何副产物。
• Design and synthesis of 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles and pyrazolo[3,4-b]pyridines for Aurora-A kinase inhibitors
  作者：Jianyou Shi、Guobin Xu、Wei Zhu、Haoyu Ye、Shengyong Yang、Youfu Luo、Jing Han、Jincheng Yang、Rui Li、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.bmcl.2010.04.083

  日期：2010.7

  Two series of 3-aminopyrazole compounds including 24 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles and 16 pyrazolo[3,4-b]pyridines were synthesized and evaluated against HCT116, A549, and A2780 tumor cell lines. Among them, three compounds were found to have the ideal anti-proliferative activities in vitro. Docking experiments showed that the novel pyrazolo[3,4-b]pyridines share the similar interaction mode with Aurora-A kinase as PHA739358. (C) 2010 Elsevier Ltd. All rights reserved.
• (3R)-4-[(3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-(2,2,2-trifluoroethyl)-1,4-diazepan-2-one, a selective dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes
  作者：Tesfaye Biftu、Dennis Feng、Xiaoxia Qian、Gui-Bai Liang、Gerard Kieczykowski、George Eiermann、Huaibing He、Barbara Leiting、Kathy Lyons、Aleksandr Petrov、Ranabir Sinha-Roy、Bei Zhang、Giovanna Scapin、Sangita Patel、Ying-Duo Gao、Suresh Singh、Joseph Wu、Xiaoping Zhang、Nancy A. Thornberry、Ann E. Weber

  DOI：10.1016/j.bmcl.2006.09.099

  日期：2007.1

  Replacement of the triazolopiperazine ring of sitagliptin (DPP-4 IC(50)=18nM) with 3-(2,2,2-trifluoroethyl)-1,4-diazepan-2-one gave dipeptidyl peptidase IV (DPP-4) inhibitor 1 which is potent (DPP-4 IC(50)=2.6nM), selective, and efficacious in an oral glucose tolerance test in mice. It was selected for extensive preclinical development as a potential back-up candidate to sitagliptin.
• Terent'ew; Buzkus, Zhurnal Obshchei Khimii, 1953, vol. 23, p. 1230,1232;engl.Ausg.S.1295,1296
  作者：Terent'ew、Buzkus

  DOI：——

  日期：——