methyl 5-[2-(tert-butoxycarbonylamino)ethyl]-1-(6-phenylpyridazin-3-yl)-1H-pyrazole-4-carboxylate | 1188338-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: methyl 5-[2-(tert-butoxycarbonylamino)ethyl]-1-(6-phenylpyridazin-3-yl)-1H-pyrazole-4-carboxylate
• 英文别名: Methyl 5-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1-(6-phenylpyridazin-3-yl)pyrazole-4-carboxylate；methyl 5-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1-(6-phenylpyridazin-3-yl)pyrazole-4-carboxylate
• CAS: 1188338-64-8
• 化学式: C₂₂H₂₅N₅O₄
• 分子量: 423.472
• InChiKey: AOLRCNDUYZIVKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-肼基-6-苯基吡嗪 、 methyl (E)-5-(tert-butoxycarbonylamino)-2-[(dimethylamino)methylidene]-3-oxopentanoate 以 甲醇 为溶剂， 反应 3.0h， 以80%的产率得到methyl 5-[2-(tert-butoxycarbonylamino)ethyl]-1-(6-phenylpyridazin-3-yl)-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  A synthesis of 1-substituted 5-[2-(acylamino)ethyl]-1H-pyrazole-4-carboxamides

  摘要：

  A seven-step synthesis of 1-substituted 5-(2-acylaminoethyl)-1H-pyi-azole-4-carboxamides 20 as the pyrazole analogues of histamine was developed. The synthesis starts with a three-step preparation of N(1)-substituted methyl 5-(2-tert-butoxycarbonylaminoethyl)-1H-pyrazole-4-carboxylates 7 from commercially available Boc-beta-alanine (1). Subsequent four-step transformation of the key-intermediates 7 into the final products 20 was performed following two complementary reaction sequences comprising acidolytic removal of the Boc group, hydrolysis of the COOMe group, amidations of the COOH group, and acylations of the NH2 group. The Structures of pyrazole derivatives were determined by spectroscopic methods and by X-ray diffraction. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2009.06.021

文献信息

• A synthesis of 1-substituted 5-[2-(acylamino)ethyl]-1H-pyrazole-4-carboxamides
  作者：David Kralj、Miha Friedrich、Uroš Grošelj、Sonja Kiraly-Potpara、Anton Meden、Jernej Wagger、Georg Dahmann、Branko Stanovnik、Jurij Svete

  DOI：10.1016/j.tet.2009.06.021

  日期：2009.8

  A seven-step synthesis of 1-substituted 5-(2-acylaminoethyl)-1H-pyi-azole-4-carboxamides 20 as the pyrazole analogues of histamine was developed. The synthesis starts with a three-step preparation of N(1)-substituted methyl 5-(2-tert-butoxycarbonylaminoethyl)-1H-pyrazole-4-carboxylates 7 from commercially available Boc-beta-alanine (1). Subsequent four-step transformation of the key-intermediates 7 into the final products 20 was performed following two complementary reaction sequences comprising acidolytic removal of the Boc group, hydrolysis of the COOMe group, amidations of the COOH group, and acylations of the NH2 group. The Structures of pyrazole derivatives were determined by spectroscopic methods and by X-ray diffraction. (C) 2009 Published by Elsevier Ltd.