2,3-Diethyl-5,6-dihydro-pyrazin | 73570-18-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,3-Diethyl-5,6-dihydro-pyrazin
• 英文别名: 5,6-Diethyl-2,3-dihydropyrazine
• CAS: 73570-18-0
• 化学式: C₈H₁₄N₂
• 分子量: 138.213
• InChiKey: JTUAKYJQMQPEJH-UHFFFAOYSA-N

物化性质

• 沸点：
  214.5±23.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-Diethyl-5,6-dihydro-pyrazin 在 rose bengal 氧气 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以49%的产率得到1-isocyano-2-(propionylamino)ethane
  参考文献：
  名称：

  Photooxygenation of 1,4-diaza-1,3-butadienes (.alpha.-diimines): formation of isonitriles

  摘要：

  Dye-sensitized photooxygenations of cyclic and acyclic 1,4-diaza-1,3-butadienes (alpha-diimines), carrying a methyl or an ethyl group in the 2-position, yield isonitriles and amides, as well as formaldehyde or acetaldehyde. Thus, cyclic alpha-diimines such as 5,6-dimethyl- (1a), 5-methyl-6-phenyl- (1b), 5-methyl-6-(p-tolyl)- (1c), and 5,6-diethyl-2,3-dihydropyrazine (1d) yield the respective 1-isocyano-2-(acylamino)ethanes 2a-d, whereas 5-isopropyl-6-phenyl- (1e) and 5,6-diphenyl-2,3-dihydropyrazine (1f) are inert toward photooxygenation. Acyclic alpha-diimines such as 1,8-bis(acetylamino)-3,6-diaza-4,5-dimethyl-3,5-octadiene (4a), 2,5-diaza-3,4-dimethyl-2,4-hexadiene (4b), 1,4-diaza-2,3-dimethyl-1,4-diphenyl-1,3-butadiene (4c), and N,N'-bis[(1S,2S,3S,5R)-pinan-3-ylmethyl]-2,3-butanediimine (4d) afford the respective isonitriles 5a-d and acetamides 6a-d. With retention of configuration, chiral alpha-diimines such as (-)-N,N'-bis[(S)-1-phenylethyl]-2,3-butanediimine [(S,S)-4e] and its R,R enantiomer [(R,R,)-4e], and (3S,8S)-(-)-3,8-dicarbomethoxy-4,7-diaza-2,5,6,9-tetramethyl-4,6-decadiene [(S,S)-4f] yield the corresponding enantiomerically pure isonitriles (S)-5e, (R)-5e, and (S)-5f and acetamides (S)-6e, (R)-6e, and (S)-6f. Evidence for a singlet oxygen reaction is presented. A working hypothesis is proposed which includes the formation of a transient hydroperoxide 7 that fragments into an isonitrile molecule, an aldehyde, and an N-alkyl- or N-arylnitrilium cation and a hydroxide ion; the latter combine to yield the amide groups in 2a-d and the amide compounds 6a-f.

  DOI：

  10.1021/jo00027a041
• 作为产物：
  描述：

  3,4-己二酮 、 乙二胺 以 水 为溶剂， 反应 0.5h， 以72%的产率得到2,3-Diethyl-5,6-dihydro-pyrazin
  参考文献：
  名称：

  喹喔啉和2,3-二氢吡嗪的绿色合成

  摘要：

  摘要 通过在水中简单地添加1,2-二胺和1,2-二羰基化合物，可以高收率获得喹喔啉和二氢吡嗪衍生物。在某些情况下，产物自发地从反应混合物中沉淀出来，使得有可能回收并再利用母液用于进一步的冷凝。非常温和的反应条件，高收率的产品以及不存在任何催化剂，使得该方法成为生产喹喔啉和二氢吡嗪的有效而绿色的途径。 通过在水中简单地添加1,2-二胺和1,2-二羰基化合物，可以高收率获得喹喔啉和二氢吡嗪衍生物。在某些情况下，产物自发地从反应混合物中沉淀出来，使得有可能回收并再利用母液用于进一步的冷凝。非常温和的反应条件，高收率的产品以及不存在任何催化剂，使得该方法成为生产喹喔啉和二氢吡嗪的有效而绿色的途径。

  DOI：

  10.1055/s-0033-1338441

文献信息

• Structure-activity relationships in prazosin-related compounds. 2. Role of the piperazine ring on .alpha.-blocking activity
  作者：Dario Giardina、Ugo Gulini、Maurizio Massi、Maria G. Piloni、Pierluigi Pompei、Giovanni Rafaiani、Carlo Melchiorre

  DOI：10.1021/jm00058a005

  日期：1993.3

  Several prazosin-related compounds have been synthesized and evaluated for their blocking activity toward a-adrenoreceptors. The structural modification performed on the prazosin structure included the replacement of the piperazine ring with 2,3-dialkylpiperazine or 1,2-cyclohexanediamine moieties to characterize a lipophilic binding pocket in the alpha1-adrenoreceptor surface. Cyclohexanediamine derivatives 3-6 were almost devoid of potency and selectivity, whereas dialkylpiperazine compounds 7-14 showed high affinity and selectivity toward alpha1-adrenoreceptors. The cis derivative 13 (cyclazosin) was the most potent and selective with an alpha1/alpha2 selectivity ratio value of 7800. The particular trend of antagonist activity within cis/trans stereoisomeric compounds not only supports the presence of a lipophilic binding area on alpha1-adrenoreceptor surface but also suggests that the lipophilic pocket is endowed with a well-defined size and spatial orientation. The most active compound of the series, 13, was tested also in vivo for antihypertensive activity on spontaneously hypertensive rats. It showed an interesting long-lasting hypotensive effect, very similar to that of doxazosin, which was statistically significant 12 h after oral administration.
• FLAMENT I.; SONNAY PH.; OHLOFF G., BULL. SOC. CHIM. BELG., 1979, 88, NO 11, 941-950
  作者：FLAMENT I.、 SONNAY PH.、 OHLOFF G.

  DOI：——

  日期：——
• SONGCHUAN, TSAI;ZHANGBEE, CHANG;WINGZIANG, WANG;MING, CHANG;SUPING, JI, J. NOMJING UNIV. NATUR. SCI. ED., 1984, N 2, 245-249
  作者：SONGCHUAN, TSAI、ZHANGBEE, CHANG、WINGZIANG, WANG、MING, CHANG、SUPING, JI

  DOI：——

  日期：——
• VERFAHREN ZUR HERSTELLUNG VON TEDA-DERIVATEN
  申请人：BASF SE

  公开号：EP2197882A2

  公开（公告）日：2010-06-23
• METHOD FOR PRODUCING TEDA DERIVATIVES
  申请人：Cauwenberge Gunther Van

  公开号：US20100204438A1

  公开（公告）日：2010-08-12

  The present invention relates to a process for preparing triethylenediamine (TEDA) derivatives, comprising the following steps: a) reacting a dihydropyrazine with an olefin, b) if appropriate hydrogenating after step a). The present invention further also relates to novel TEDA derivatives as such and to their use as incorporable polyurethane catalysts.