2-氰基-2-吡啶-3-乙酸乙酯 | 39266-24-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氰基-2-吡啶-3-乙酸乙酯
• 英文名称: α-cyanopyridine-3-acetate
• 英文别名: ethyl 2-(3-pyridinyl)-cyanoacetate；ethyl 2-cyano-2-(pyridin-3-yl)acetate；Pyridyl-(3)-cyanessigsaeure-ethylester；cyano-pyridin-3-yl-acetic acid ethyl ester；Ethyl 2-cyano-2-pyridin-3-YL-acetate；ethyl 2-cyano-2-pyridin-3-ylacetate
• CAS: 39266-24-5
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: HIUYWGBJSNFGKT-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  333.8±27.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 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：
  63
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-氰基-2-吡啶-3-乙酸乙酯 在 盐酸 作用下， 以 甲酸 为溶剂， 生成 ethyl 3-amino-3-oxo-2-(pyridin-3-yl)propanoate
  参考文献：
  名称：

  Managing Highly Coordinative Substrates in Asymmetric Catalysis: A Catalytic Asymmetric Amination with a Lanthanum-Based Ternary Catalyst

  摘要：

  Full details of a catalytic asymmetric amination with a lanthanum/amide-based ligand catalyst system are described. A catalyst comprising La(NO3)(3)center dot 6H(2)O, (R)-3a and H-D-Val-V'Bu was identified to promote the catalytic asymmetric amination of nonprotected succinimide derivative 1 with as little as 1 mol % catalyst loading Mechanistic studies by various spectroscopic analyses and several control and kinetic experiments suggested that the catalyst components were in equilibrium between the associated and dissociated forms, and that the reaction likely proceeded through a La(NO3)(3)center dot 6H(2)O/(R)-3a/H-D-Val-O'Bu ternary complex. This catalyst system was also effective for asymmetric amination of N-nonsubstituted alpha-alkoxycarbonyl amides 7, hitherto unprecedented substrates in asymmetric catalysis, probably due to their attenuated reactivity and difficult stereocontrol, affording the amination products in up to > 99% yield and > 99% ee. The high catalytic performance and enantiocontrol of the reaction with highly coordinative substrates were achieved by the activation/recognition of the substrates exerted by coordination to lanthanum and hydrogen bonding cooperatively in the transition state.

  DOI：

  10.1021/ja9052653
• 作为产物：
  描述：

  3-溴吡啶 、 氰乙酸乙酯 在 苯并恶唑 、 potassium phosphate 、 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以78%的产率得到2-氰基-2-吡啶-3-乙酸乙酯
  参考文献：
  名称：

  以 1,3-苯并恶唑为配体，碘化铜 (I) 催化丙二酸二乙酯与 (杂) 芳基溴化物的 (杂) 芳基化

  摘要：

  提出了在碘化铜 (I) 和 1,3-苯并恶唑存在下芳基溴化物与丙二酸二乙酯的有效 Ullmann 型偶联。该方法具有广泛的底物范围（杂环和苯基溴化物）和良好的官能团耐受性（OMe、Me、Ac、CN、NO2、F 和 Cl）。此外，达到完全转化所需的时间更少（3-9 小时）。

  DOI：

  10.1055/s-0036-1591210
• 作为试剂：
  描述：

  氰乙酸乙酯 、 3-溴吡啶 、 potassium tert-butylate 、 溶剂黄146 在 1,1'-双(二苯基膦)二茂铁 、 醋酸钯 二氯甲烷 、 Sodium sulfate-III 、 silica gel 、 ethyl acetate petroleum ether 、 2-氰基-2-吡啶-3-乙酸乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.17h， 以This resulted in 4.6 g (54%) of ethyl 2-cyano-2-(pyridin-3-yl)acetate as a yellow solid的产率得到2-氰基-2-吡啶-3-乙酸乙酯
  参考文献：
  名称：

  HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

  摘要：

  本文介绍了新的杂环化合物和组合物，以及它们作为治疗疾病的药物的应用。还提供了抑制人类或动物主体中PAS激酶（PASK）活性的方法，用于治疗糖尿病等疾病。

  公开号：

  US20120277224A1

文献信息

• Heterocyclic compounds for the inhibition of pask
  申请人：McCall John M.

  公开号：US10953012B2

  公开（公告）日：2021-03-23

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文公开了新的杂环化合物和组合物及其作为药物治疗疾病的应用。还提供了抑制人或动物体内 PAS 激酶（PASK）活性的方法，用于治疗糖尿病等疾病。
• Palladium-Catalyzed One-Pot Synthesis of 2-Alkyl-2-arylcyanoacetates
  作者：Xiang Wang、Anil Guram、Emilio Bunel、Guo-Qiang Cao、Jennifer R. Allen、Margaret M. Faul

  DOI：10.1021/jo7024338

  日期：2008.2.1

  [GRAPHICS]A one-pot procedure for the synthesis of 2-alkyl-2-arylcyanoacetates based on a Pd(OAc)(2)/DPPF (DPPF = 1,1'-diphenylphosphino ferreocene)-catalyzed enolate arylation followed by in situ alkylation has been developed. This procedure tolerates a diverse range of aryl and heteroaryl bromides, and provides a rapid entry to a variety of 2-alkyl-2-arylcyanoacetates in good to excellent yield.
• Is Selective Monosubstitution of Dihalides via SRN1 Reaction Feasible? An Electrochemical Approach for Dichloroarenes
  作者：Christian Amatore、Catherine Combellas、Nour-Eddine Lebbar、Andre Thiebault、Jean-Noeel Verpeaux

  DOI：10.1021/jo00106a009

  日期：1995.1

  1,4-Dichlorobenzene and dichloropyridines undergo S(RN)1 reactions with various nucleophiles upon electrochemical initiation. Substitution can compete with reduction only when indirect electrolyses at low current are performed. Selective formation of monosubstitution products is observed when the nucleophiles used behave as electron-donating groups when attached to the aromatic moiety, a situation which is just the opposite of what had been observed when the same reactions were initiated photochemically. This surprising difference in behavior can be rationalized in terms of different capabilities of both activation methods to generate the key monosubstitution anion radical, ArNuX(.-). Kinetic and thermodynamic data concerning the reactivity of dichloroarenes in such processes are presented and discussed.
• Sakamoto, Takao; Katoh, Eisaku; Kondo, Yoshinori, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 5, p. 1664 - 1668
  作者：Sakamoto, Takao、Katoh, Eisaku、Kondo, Yoshinori、Yamanaka, Hiroshi

  DOI：——

  日期：——
• Banashek,A.; Shchukina,M.N., Journal of general chemistry of the USSR, 1961, vol. 31, p. 1378 - 1381
  作者：Banashek,A.、Shchukina,M.N.

  DOI：——

  日期：——