Isobutyl-[1-pyridin-4-yl-meth-(Z)-ylidene]-amine | 73684-34-1

• 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
• 英文名称: Isobutyl-[1-pyridin-4-yl-meth-(Z)-ylidene]-amine
• 英文别名: 4-Pyridylmethylidene-isobutylamine；N-(2-methylpropyl)-1-pyridin-4-ylmethanimine
• CAS: 73684-34-1
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: NCXMKHISLYJIFE-UHFFFAOYSA-N

物化性质

• 沸点：
  257.9±13.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Isobutyl-[1-pyridin-4-yl-meth-(Z)-ylidene]-amine 在 溶剂黄146 、 1-丙基磷酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  Hit-to-Lead Studies for the Antimalarial Tetrahydroisoquinolone Carboxanilides

  摘要：

  Phenotypic whole-cell screening in erythrocytic cocultures of Plasmodium falciparum identified a series of dihydroisoquinolones that possessed potent antimalarial activity against multiple resistant strains of P. falciparum in vitro and show no cytotoxicity to mammalian cells. Systematic structure activity studies revealed relationships between potency and modifications at N-2, C-3, and C-4. Careful structure property relationship studies, coupled with studies of metabolism, addressed the poor aqueous solubility and metabolic vulnerability, as well as potential toxicological effects, inherent in the more potent primary screening hits such as 10b. Analogues 13h and 13i, with structural modifications at each site, were shown to possess excellent antimalarial activity in vivo. The (+)-(35,4S) enantiomer of 13i and similar analogues were identified as the more potent. On the basis of these studies, we have selected (+)-13i for further study as a preclinical candidate.

  DOI：

  10.1021/acs.jmedchem.6b00752
• 作为产物：
  描述：

  Isobutylidene-4-aminomethylpyridine 、 potassium tert-butylate 在 甲苯 、 水 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以to obtain 85 g (0.525 mol) of 4-pyridylmethylidene-isobutylamine as a slightly yellowish liquid的产率得到Isobutyl-[1-pyridin-4-yl-meth-(Z)-ylidene]-amine
  参考文献：
  名称：

  Process for producing hydrazone derivatives of pyridinaldehydes

  摘要：

  本发明涉及一种改进的制备吡啶醛和其酰肼衍生物的方法，例如，吡啶醛-苯基肼衍生物。该方法包括将氨甲基吡啶与醛或酮反应，得到式子##STR1##的化合物，将该化合物(III)在适当的催化剂存在下异构化为式子##STR2##的化合物，然后在酸的存在下，并且在需要时在肼的存在下，将化合物(V)转化为吡啶醛或吡啶醛-酰肼。本发明的方法可以在温和、对生态环境有利的条件下简单地制备吡啶醛和吡啶醛-酰肼，并且产率良好。

  公开号：

  US04237275A1

文献信息

• Process for producing hydrazone derivatives of pyridinaldehydes
  申请人：Ciba-Geigy Corporation

  公开号：US04237275A1

  公开（公告）日：1980-12-02

  An improved process for producing pyridinaldehydes and hydrazone derivatives thereof, for example, pyridinaldehyde-phenylhydrazones, is described. This comprises reacting a aminomethylpyridine with an aldehyde or a ketone to give a compound of the formula ##STR1## isomerizing the compound (III), in the presence of suitable catalysts, to a compound of the formula ##STR2## and converting the compound (V), in the presence of an acid and optionally in the presence of a hydrazine, into a pyridinaldehyde or a pyridinaldehyde-hydrazone. It is possible to produce by the process according to the invention pyridinaldehydes and pyridinaldehyde-hydrazones in a simple manner, under mild ecologically favorable conditions and in good to very good yields.

  本发明涉及一种改进的制备吡啶醛和其酰肼衍生物的方法，例如，吡啶醛-苯基肼衍生物。该方法包括将氨甲基吡啶与醛或酮反应，得到式子##STR1##的化合物，将该化合物(III)在适当的催化剂存在下异构化为式子##STR2##的化合物，然后在酸的存在下，并且在需要时在肼的存在下，将化合物(V)转化为吡啶醛或吡啶醛-酰肼。本发明的方法可以在温和、对生态环境有利的条件下简单地制备吡啶醛和吡啶醛-酰肼，并且产率良好。
• Boduszek, Bogdan; Wieczorek, Jan S., Journal fur praktische Chemie (Leipzig 1954), 1986, vol. 328, # 4, p. 627 - 634
  作者：Boduszek, Bogdan、Wieczorek, Jan S.

  DOI：——

  日期：——
• Hit-to-Lead Studies for the Antimalarial Tetrahydroisoquinolone Carboxanilides
  作者：David M. Floyd、Philip Stein、Zheng Wang、Jian Liu、Steve Castro、Julie A. Clark、Michele Connelly、Fangyi Zhu、Gloria Holbrook、Amy Matheny、Martina S. Sigal、Jaeki Min、Rajkumar Dhinakaran、Senthil Krishnan、Sridevi Bashyum、Spencer Knapp、R. Kiplin Guy

  DOI：10.1021/acs.jmedchem.6b00752

  日期：2016.9.8

  Phenotypic whole-cell screening in erythrocytic cocultures of Plasmodium falciparum identified a series of dihydroisoquinolones that possessed potent antimalarial activity against multiple resistant strains of P. falciparum in vitro and show no cytotoxicity to mammalian cells. Systematic structure activity studies revealed relationships between potency and modifications at N-2, C-3, and C-4. Careful structure property relationship studies, coupled with studies of metabolism, addressed the poor aqueous solubility and metabolic vulnerability, as well as potential toxicological effects, inherent in the more potent primary screening hits such as 10b. Analogues 13h and 13i, with structural modifications at each site, were shown to possess excellent antimalarial activity in vivo. The (+)-(35,4S) enantiomer of 13i and similar analogues were identified as the more potent. On the basis of these studies, we have selected (+)-13i for further study as a preclinical candidate.
• Process for producing pyridinaldehydes
  申请人：Ciba-Geigy Corporation

  公开号：US04322536A1

  公开（公告）日：1982-03-30

  A new improved process for producing pyridinaldehydes and hydrazone derivatives thereof, for example, pyridinaldehyde-phenylhydrazones, is described. This comprises reacting an aminomethylpyridine with an aldehyde or a ketone to give a compound of the formula ##STR1## isomerizing the compound (III), in the presence of suitable catalysts, to a compound of the formula ##STR2## and converting the compound (V), in the presence of an acid and optionally in the presence of a hydrazine, into a pyridinaldehyde or a pyridinaldehyde-hydrazone. It is possible to produce by the process according to the invention pyridinaldehydes and pyridinaldehyde-hydrazones in a simple manner, under mild ecologically favorable conditions and in good to very good yields.

  本发明涉及一种生产吡啶醛及其酰肼衍生物（例如，吡啶醛-苯基肼）的新改进工艺。该工艺包括将氨甲基吡啶与醛或酮反应，得到式（III）的化合物，其中R1和R2分别为氢、烷基或芳基；在适当的催化剂存在下使化合物（III）异构化为式（V）的化合物，其中R3为氢、烷基或芳基；在酸存在下，可选地在肼存在下，将化合物（V）转化为吡啶醛或吡啶醛-酰肼。本发明的工艺可以在温和、环保的条件下，简单地制备出吡啶醛和吡啶醛-酰肼，并且收率良好。