3-amino-4-methylpent-2-enenitrile | 52731-60-9

• 物质功能分类: 化学试剂 - 有机试剂 - 烯烃（环状与无环状）
• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-amino-4-methylpent-2-enenitrile
• 英文别名: 3-amino-4-methyl-2-pentenenitrile；3-Amino-4-methyl-2-pentenenitrile
• CAS: 52731-60-9
• 化学式: C₆H₁₀N₂
• mdl: MFCD19227943
• 分子量: 110.159
• InChiKey: DUDWHIZGKCRFIB-UHFFFAOYSA-N

物化性质

• 沸点：
  273.7±13.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-amino-4-methylpent-2-enenitrile 在 sodium sulfide 、 硫化氢 、 四丁基氯化铵 、 碘 、 potassium carbonate 作用下， 以 乙醚 、 水 、 苯 为溶剂， 生成 3-isopropyl-isothiazol-5-ylamine
  参考文献：
  名称：

  Hackler, Ronald E.; Burow, Kenneth W.; Kaster, Sylvester V., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1575 - 1578

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氧代-4-甲基戊腈 在 硝酸铵 、 氨 作用下， 以 乙醇 为溶剂， 生成 3-amino-4-methylpent-2-enenitrile
  参考文献：
  名称：

  Hackler, Ronald E.; Burow, Kenneth W.; Kaster, Sylvester V., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1575 - 1578

  摘要：

  DOI：
• 作为试剂：
  描述：

  丁烯-2-醛 在 3-amino-4-methylpent-2-enenitrile 、 吡咯烷盐酸盐 作用下， 以 氘代乙腈 为溶剂， 反应 16.0h， 生成 正丁醛
  参考文献：
  名称：

  烯胺与不饱和醛和酮的形式 (3+3) 环加成合成取代吡啶

  摘要：

  描述了一种有机催化的形式 (3+3) 环加成反应，用于实际合成取代的吡啶。从现成的烯胺和烯/烯/烯酮底物开始，该协议提供了带有各种官能团的三或四取代吡啶支架。该方法在 50 g 规模上进行了演示，能够合成 2-isopropyl-4-methylpyridin-3-amine，这是一种用于制造 sotorasib 的原材料。使用二维核磁共振 (NMR) 光谱法进行的机理分析表明，转化过程是通过在吡啶形成之前可逆地形成稳定的非循环反应物质来进行的。采用原位反应进展动力学分析和对照 NMR 研究来更好地了解 FeCl 的作用3与盐酸吡咯烷促进反应。

  DOI：

  10.1021/acs.joc.2c00576

文献信息

• [EN] BI- AND TRICYCLIC INDAZOLE-SUBSTITUTED 1,4-DIHYDROPYRIDINE DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS DE 1,4-DIHYDROPYRIDINE SUBSTITUÉS PAR INDAZOLE BI- ET TRICYCLIQUES ET LEURS UTILISATIONS
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2010094405A1

  公开（公告）日：2010-08-26

  This invention relates to novel bi- and tricyclic indazole-substituted 1,4-dihydropyridine derivatives having protein tyrosine kinase inhibitory activity, to a process for the manufacture thereof and to the use thereof for the treatment of c-Met-mediated diseases or c-Met-mediated conditions, particularly cancer and other proliferative disorders.

  本发明涉及具有蛋白酪氨酸激酶抑制活性的新型双环和三环吲唑取代的1,4-二氢吡啶衍生物，以及其制备方法和用于治疗c-Met介导疾病或c-Met介导病症，特别是癌症和其他增殖性疾病的用途。
• BI- AND TRICYCLIC INDAZOLE-SUBSTITUTED 1,4-DIHYDROPYRIDINE DERIVATIVES AND USES THEREOF
  申请人：Michels Martin

  公开号：US20120035409A1

  公开（公告）日：2012-02-09

  This invention relates to novel bi- and tricyclic indazole-substituted 1,4-dihydropyridine derivatives having protein tyrosine kinase inhibitory activity, to a process for the manufacture thereof and to the use thereof for the treatment of c-Met-mediated diseases or c-Met-mediated conditions, particularly cancer and other proliferative disorders.

  本发明涉及一种具有蛋白酪氨酸激酶抑制活性的新型双环和三环吲唑取代的1,4-二氢吡啶衍生物，以及其制造方法和用于治疗c-Met介导的疾病或c-Met介导的疾病状态，特别是癌症和其他增殖性疾病的用途。
• Bi- and tricyclic indazole-substituted 1,4-dihydropyridine derivatives and uses thereof
  申请人：Michels Martin

  公开号：US08759341B2

  公开（公告）日：2014-06-24

  This invention relates to novel bi- and tricyclic indazole-substituted 1,4-dihydropyridine derivatives having protein tyrosine kinase inhibitory activity, to a process for the manufacture thereof and to the use thereof for the treatment of c-Met-mediated diseases or c-Met-mediated conditions, particularly cancer and other proliferative disorders.

  本发明涉及一种新型的双环和三环吲哚取代的1,4-二氢吡啶衍生物，具有蛋白酪氨酸激酶抑制活性，以及其制造方法和用于治疗c-Met介导的疾病或c-Met介导的病症，特别是癌症和其他增生性疾病的用途。
• Pyrazole Bioisosteres of Leflunomide as B-Cell Immunosuppressants for Xenotransplantation and Chronic Rejection:  Scope and Limitations
  作者：Christos Papageorgiou、Rainer Albert、Philipp Floersheim、Michel Lemaire、Francis Bitch、Hans-Peter Weber、Elsebeth Andersen、Valerie Hungerford、Max H. Schreier

  DOI：10.1021/jm981028c

  日期：1998.8.1

  T-cell immunosuppressant-based therapies efficiently control early graft rejection in allotransplantation settings. They fail, however, to prevent those rejection events which are mediated by transplant-induced antibody (Ab) responses such as those involved in xenograft and chronic allograft rejection. This is mainly due to their inability to block T-cell-independent Ab production against the transplanted organs. The bioactive metabolite 2(Z) of leflunomide (1) inhibits the formation of such Ab, but the drug has pharmacokinetic properties and a therapeutic window incompatible with transplantation indications. Pyrazole 3, a constrained analogue of 2(Z), was designed and shown to be conformationally and biologically similar to 2(Z). Further investigations with derivatives of 3 demonstrated that the pyrazoles had very tight structure-activity relationships, the only equipotent compound being 3o. However, in contrast to 2(Z), both 3 and 3o were inactive in vivo due to short half-life and drug concentrations lower than the in vitro obtained IC50 values, Compound 3o inhibits T-cell-independent Ab production by a different biochemical mechanism from that of 2(Z) and 3 and may therefore represent a valuable tool for the identification of new targets for B-cell inhibition.
• One-step synthesis of thiazolo[3,2-a]pyridines by a multicomponent reaction of β-enaminonitriles, α,β-unsaturated aldehydes, and 2-aminothiol hydrochlorides
  作者：Mónica Pérez Perrino、Rafael del Villar-Guerra、M. Carmen Sañudo、Luis A. Calvo、Alfonso González-Ortega

  DOI：10.1016/j.tet.2010.02.051

  日期：2010.4

  A wide library of 3,7,8,8a-tetrahydro-2H-thiazolo[3,2-a]pyridines has been prepared by simple heating in acetonitrile of beta-enaminonitriles, alpha,beta-unsaturated aldehydes and 2-aminothiol hydrochlorides. Chemical yields depend on the nature, hindrance, and position of the substituents. The scope, limitations, and stereocontrol associated to this three-component reaction have been studied in detail. In general, the diastereoinduction observed in the three new stereogenic centers generated in the pro-chiral alpha,beta-unsaturated aldehyde is low. (C) 2010 Elsevier Ltd. All rights reserved.