3-(呋喃-2-基)丙-2-烯-1-胺 | 300687-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 3-(呋喃-2-基)丙-2-烯-1-胺
• 英文名称: N-Furfurylidenethylamin
• 英文别名: 3-(furan-2-yl)prop-2-en-1-amine
• CAS: 300687-38-1
• 化学式: C₇H₉NO
• 分子量: 123.155
• InChiKey: FDGZUEQNFJPGFA-UHFFFAOYSA-N

物化性质

• 沸点：
  219.6±28.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-呋喃丙烯醛 、 (S)-(-)- α-甲基苄胺 在 磷酸吡哆醛 、 recombinant ω-transaminase from Burkholderia vietnamiensis G4 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.08h， 生成 3-(呋喃-2-基)丙-2-烯-1-胺 、 苯乙酮
  参考文献：
  名称：

  Substrate profile of an ω-transaminase from Burkholderia vietnamiensis and its potential for the production of optically pure amines and unnatural amino acids

  摘要：

  A new (S)-enantioselective omega-transaminase (omega-TA) gene from Burkholderia vietnamiensis G4 was functionally expressed in Escherichia coli BL21 (DE3), and the purified recombinant N-terminal His-tagged (omega-TA (HBV-omega-TA) had a dimeric structure with optimum pH and temperature of 8.4 and 40 degrees C, respectively. The enzyme showed higher activities toward aromatic amines than aliphatic amines and (S)-1-methylbenzylamine ((S)-alpha-MBA) was the most active amino donor. For amino acceptor, keto acids, keto esters and aldehydes were more reactive than ketones with pyruvate ethyl ester being most active. Several chiral amines and unnatural amino acids or esters were synthesized using HBV-w-TA as the catalyst and isopropylamine or (S)-alpha-MBA as amino donor. Notably, HBV-omega-TA catalyzed the amino transfer to beta-keto esters to give optically pure beta-amino acid esters. In addition, glyoxylate was used as amino acceptor for the first time in the kinetic resolution of racemic amines and optically pure amines, such as (R)-1-methylbenzylamine, (R)-1-phenylpropylamine, (R)-2-amino-4-phenylbutane and (R)-1-aminotetraline, were obtained. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.11.013

文献信息

• Microwave-assisted, Mo(CO)6-mediated, palladium-catalyzed amino-carbonylation of aryl halides using allylamine: from exploration to scale-up
  作者：Prasad Appukkuttan、Linda Axelsson、Erik Van der Eycken、Mats Larhed

  DOI：10.1016/j.tetlet.2008.07.053

  日期：2008.9

  Palladium-catalyzed aminocarbonylations of various (hetero)aryl halides with allylamine using Mo(CO)6 as a solid, in situ CO source, were explored. Microwave-enhanced conditions proved to be highly useful in promoting the conversions in a mere 10–20 min with various (hetero)aryl iodides, bromides and chlorides. The scale-up of a microwave-enhanced aminocarbonylation to 25 mmol scale was performed successfully

  探索了使用Mo（CO）6作为固体原位CO源，用烯丙基胺对各种（杂）芳基卤化物进行钯催化的氨基羰基化反应。事实证明，微波增强条件对于在短短10-20分钟内促进各种（杂）芳基碘化物，溴化物和氯化物的转化非常有用。成功地将微波增强的氨基羰基化规模放大到25 mmol。
• US4139560A
  申请人：——

  公开号：US4139560A

  公开（公告）日：1979-02-13
• Substrate profile of an ω-transaminase from Burkholderia vietnamiensis and its potential for the production of optically pure amines and unnatural amino acids
  作者：Jinju Jiang、Xi Chen、Jinhui Feng、Qiaqing Wu、Dunming Zhu

  DOI：10.1016/j.molcatb.2013.11.013

  日期：2014.2

  A new (S)-enantioselective omega-transaminase (omega-TA) gene from Burkholderia vietnamiensis G4 was functionally expressed in Escherichia coli BL21 (DE3), and the purified recombinant N-terminal His-tagged (omega-TA (HBV-omega-TA) had a dimeric structure with optimum pH and temperature of 8.4 and 40 degrees C, respectively. The enzyme showed higher activities toward aromatic amines than aliphatic amines and (S)-1-methylbenzylamine ((S)-alpha-MBA) was the most active amino donor. For amino acceptor, keto acids, keto esters and aldehydes were more reactive than ketones with pyruvate ethyl ester being most active. Several chiral amines and unnatural amino acids or esters were synthesized using HBV-w-TA as the catalyst and isopropylamine or (S)-alpha-MBA as amino donor. Notably, HBV-omega-TA catalyzed the amino transfer to beta-keto esters to give optically pure beta-amino acid esters. In addition, glyoxylate was used as amino acceptor for the first time in the kinetic resolution of racemic amines and optically pure amines, such as (R)-1-methylbenzylamine, (R)-1-phenylpropylamine, (R)-2-amino-4-phenylbutane and (R)-1-aminotetraline, were obtained. (C) 2013 Elsevier B.V. All rights reserved.