1-烯丙基-1.2-二甲酰基肼 | 216854-53-4

• 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: 1-烯丙基-1.2-二甲酰基肼
• 中文别名: 1-(2-丙烯基)-1,2-肼二甲醛
• 英文名称: 1-allyl-1,2-diformylhydrazine
• 英文别名: N-allyl-N'-formylformic hydrazide；N-[formyl(prop-2-enyl)amino]formamide
• CAS: 216854-53-4
• 化学式: C₅H₈N₂O₂
• mdl: MFCD01871488
• 分子量: 128.131
• InChiKey: DQMKUGFVTHUUDL-UHFFFAOYSA-N

物化性质

• 沸点：
  191℃
• 密度：
  1.096
• 闪点：
  70℃

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-烯丙基-1.2-二甲酰基肼 在 溴 、 potassium carbonate 、 lithium bromide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.17h， 生成 4-溴-1,2-二甲酰基吡唑烷
  参考文献：
  名称：

  New Straightforward Synthesis and Characterization of a Unique 1β-Methylcarbapenem Antibiotic Biapenem Bearing a σ-Symmetric Bicyclotriazoliumthio Group as the Pendant Moiety

  摘要：

  Biapenem 1, (1R,5S,6S,)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)thio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate, is a new non-natural 1 beta-methylcarbapenem antibiotic which exhibits a wide range of antibacterial activity, remarkable chemical stability, and extensive stability against human renal dehydropeptidase-I. Mercaptobicyclotriazolium chloride 2 useful for the pendant moiety of 1 was successfully synthesized starting from hydrazine hydrate 3 along an economically available synthetic route. The thiol 2 was efficiently exploited for an expeditious synthesis of biapenem 1. Characterization (crystal structure, nonbonded S---O interaction, conformational analysis, and CH- - -O hydrogen bonds) of 1 was investigated by its X-ray crystallographic, H-1 NMR, and deuteration experiment analyses.

  DOI：

  10.1021/jo980462j
• 作为产物：
  描述：

  甲酸 、 1-allyl-1-formyl-2-isopropylidenehydrazine 反应 15.0h， 以90%的产率得到1-烯丙基-1.2-二甲酰基肼
  参考文献：
  名称：

  New Straightforward Synthesis and Characterization of a Unique 1β-Methylcarbapenem Antibiotic Biapenem Bearing a σ-Symmetric Bicyclotriazoliumthio Group as the Pendant Moiety

  摘要：

  Biapenem 1, (1R,5S,6S,)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)thio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate, is a new non-natural 1 beta-methylcarbapenem antibiotic which exhibits a wide range of antibacterial activity, remarkable chemical stability, and extensive stability against human renal dehydropeptidase-I. Mercaptobicyclotriazolium chloride 2 useful for the pendant moiety of 1 was successfully synthesized starting from hydrazine hydrate 3 along an economically available synthetic route. The thiol 2 was efficiently exploited for an expeditious synthesis of biapenem 1. Characterization (crystal structure, nonbonded S---O interaction, conformational analysis, and CH- - -O hydrogen bonds) of 1 was investigated by its X-ray crystallographic, H-1 NMR, and deuteration experiment analyses.

  DOI：

  10.1021/jo980462j

文献信息

• Design and Preclinical Characterization Program toward Asundexian (BAY 2433334), an Oral Factor XIa Inhibitor for the Prevention and Treatment of Thromboembolic Disorders
  作者：Susanne Roehrig、Jens Ackerstaff、Eloísa Jiménez Núñez、Henrik Teller、Pascal Ellerbrock、Katharina Meier、Stefan Heitmeier、Adrian Tersteegen、Jan Stampfuss、Dieter Lang、Karl-Heinz Schlemmer、Martina Schaefer、Kersten M. Gericke、Tom Kinzel、Daniel Meibom、Martina Schmidt、Christoph Gerdes、Markus Follmann、Alexander Hillisch

  DOI：10.1021/acs.jmedchem.3c00795

  日期：2023.9.14
• New Straightforward Synthesis and Characterization of a Unique 1β-Methylcarbapenem Antibiotic Biapenem Bearing a σ-Symmetric Bicyclotriazoliumthio Group as the Pendant Moiety
  作者：Toshio Kumagai、Satoshi Tamai、Takao Abe、Hiroshi Matsunaga、Kazuhiko Hayashi、Ikuo Kishi、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.1021/jo980462j

  日期：1998.11.1

  Biapenem 1, (1R,5S,6S,)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)thio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate, is a new non-natural 1 beta-methylcarbapenem antibiotic which exhibits a wide range of antibacterial activity, remarkable chemical stability, and extensive stability against human renal dehydropeptidase-I. Mercaptobicyclotriazolium chloride 2 useful for the pendant moiety of 1 was successfully synthesized starting from hydrazine hydrate 3 along an economically available synthetic route. The thiol 2 was efficiently exploited for an expeditious synthesis of biapenem 1. Characterization (crystal structure, nonbonded S---O interaction, conformational analysis, and CH- - -O hydrogen bonds) of 1 was investigated by its X-ray crystallographic, H-1 NMR, and deuteration experiment analyses.