Ethyl 1-azidocyclopropanecarboxylate | 82997-99-7

• 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
• 英文名称: Ethyl 1-azidocyclopropanecarboxylate
• 英文别名: Ethyl 1-azidocyclopropane-1-carboxylate
• CAS: 82997-99-7
• 化学式: C₆H₉N₃O₂
• 分子量: 155.156
• InChiKey: CJESKSBIBBFDBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 1-azidocyclopropanecarboxylate 在 水 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以2.81 g的产率得到1-叠氮环丙烷-1-羧酸
  参考文献：
  名称：

  Synthesis of the Cytotrienin A CoreviaMetal Catalyzed C−C Coupling

  摘要：

  A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which Is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Finally, ring-closing metathesis delivers the cytotrienin core.

  DOI：

  10.1021/ol200160p
• 作为产物：
  描述：

  3-Azido-4,5-dihydro-3H-pyrazole-3-carboxylic acid ethyl ester 以 四氯化碳 为溶剂， 反应 2.0h， 生成 Ethyl 1-azidocyclopropanecarboxylate
  参考文献：
  名称：

  Synthesis of 1-azidocyclopropanecarboxylates from 2-azido-2alkenoates

  摘要：

  DOI：

  10.1016/s0040-4039(00)87272-x

文献信息

• A Fast Procedure for the Preparation of Amides/Peptides from Carboxylic Acids and Azides via Two Redox Reactions: Application to the Synthesis of Methionine Enkephalin
  作者：Sunil K. Ghosh、Rekha Verma、Usha Ghosh、Vasant R. Mamdapur

  DOI：10.1246/bcsj.69.1705

  日期：1996.6

  A one-pot self regulated approach for the synthesis of amides/peptides based on two reduction–oxidation (redox) reactions has been described. The primary and secondary amides/peptides are made by using azidotrimethylsilane and alkyl azides/α-azido acid derivatives respectively as the direct source of amine components. Benzeneselenol, generated in the reaction medium during carboxyl activation, has

  已经描述了基于两个还原-氧化（氧化还原）反应的用于合成酰胺/肽的一锅自调节方法。一级和二级酰胺/肽分别使用叠氮三甲基硅烷和烷基叠氮化物/α-叠氮酸衍生物作为胺组分的直接来源制备。已发现在羧基活化过程中在反应介质中产生的苯甲酚是用于将叠氮化物转化为伯胺的有效还原剂。该方法已应用于甲硫氨酸脑啡肽的合成。
• One pot amide/ peptide synthesis via two redox reactions
  作者：Sunil K. Ghosh、Usha Singh、Vasant R. Mamdapur

  DOI：10.1016/s0040-4039(00)77720-3

  日期：1992.2

  A new and highly efficient one-pot self-regulated approach to amide/ peptide synthesis has been developed based on two redox reactions using azide as a latent amine component. For the first time, selenophenol, generated in situ has been found to be an effective reducing agent for the conversion of azides to amines.
• HIYAMA, TAMEJIRO;KAI, MARIKO, TETRAHEDRON LETT., 1982, 23, N 20, 2103-2104
  作者：HIYAMA, TAMEJIRO、KAI, MARIKO

  DOI：——

  日期：——
• Synthesis of the Cytotrienin A Core<i>via</i>Metal Catalyzed C−C Coupling
  作者：Michael Rössle、David J. Del Valle、Michael J. Krische

  DOI：10.1021/ol200160p

  日期：2011.3.18

  A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which Is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Finally, ring-closing metathesis delivers the cytotrienin core.
• Synthesis of 1-azidocyclopropanecarboxylates from 2-azido-2alkenoates
  作者：Tamejiro Hiyama、Mariko Kai

  DOI：10.1016/s0040-4039(00)87272-x

  日期：1982.1