8-Hydrazinyl-5-propyl-1,2,3,4-tetrahydropyrimido[4',5':4,5]furo[2,3-c]isoquinoline | 899411-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: 8-Hydrazinyl-5-propyl-1,2,3,4-tetrahydropyrimido[4',5':4,5]furo[2,3-c]isoquinoline
• 英文别名: (8-propyl-11-oxa-9,14,16-triazatetracyclo[8.7.0.02,7.012,17]heptadeca-1(10),2(7),8,12(17),13,15-hexaen-13-yl)hydrazine
• CAS: 899411-46-2
• 化学式: C₁₆H₁₉N₅O
• 分子量: 297.36
• InChiKey: TXCRFAUDJYQEOA-UHFFFAOYSA-N

物化性质

• 沸点：
  496.0±55.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-Hydrazinyl-5-propyl-1,2,3,4-tetrahydropyrimido[4',5':4,5]furo[2,3-c]isoquinoline 在 甲酸 作用下， 反应 6.0h， 生成 11-propyl-7,8,9,10-tetrahydro[1,2,4]triazolo[5'',1'':6',1']pyrimido[4',5':4,5]-furo[2,3-c]isoquinoline
  参考文献：
  名称：

  New heterocyclic systems based on 5,6,7,8-tetrahydroisoquinolines

  摘要：

  A method has been developed for the synthesis of new 8-amino-substituted 5-propyl(isobutyl)-1,2,3,4-tetra-hydropyrimido[4',5':4,5]furo[2,3-c]isoquinolines from 3-oxo derivatives of 5,6,7,8-tetra-hydroisoquinolines. Isomeric triazoles, condensed at the edge [c] of the pyrimidine ring, have been obtained from the 8-hydrazino derivatives. A Dimroth rearrangement was carried out in acidic medium.

  DOI：

  10.1007/s10593-013-1192-6
• 作为产物：
  描述：

  3-oxo-1-propyl-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile 在 hydrazine hydrate 、 sodium ethanolate 、 potassium carbonate 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 8-Hydrazinyl-5-propyl-1,2,3,4-tetrahydropyrimido[4',5':4,5]furo[2,3-c]isoquinoline
  参考文献：
  名称：

  New heterocyclic systems based on 5,6,7,8-tetrahydroisoquinolines

  摘要：

  A method has been developed for the synthesis of new 8-amino-substituted 5-propyl(isobutyl)-1,2,3,4-tetra-hydropyrimido[4',5':4,5]furo[2,3-c]isoquinolines from 3-oxo derivatives of 5,6,7,8-tetra-hydroisoquinolines. Isomeric triazoles, condensed at the edge [c] of the pyrimidine ring, have been obtained from the 8-hydrazino derivatives. A Dimroth rearrangement was carried out in acidic medium.

  DOI：

  10.1007/s10593-013-1192-6

文献信息

• Synthesis and structure of condensed triazolo- and tetrazolopyrimidines
  作者：Samvel N. Sirakanyan、Athina Geronikaki、Domenico Spinelli、Anush A. Hovakimyan、Azat S. Noravyan

  DOI：10.1016/j.tet.2013.10.015

  日期：2013.12

  Herein we present the synthesis of several new hydrazino derivatives of cyclopenta[c]pyridine, 5,6,7,8-tetrahydroisoquinoline and pyrano[3,4-c]pyridine from 3-oxo-4-cyano fused pyridine derivatives. The hydrazino derivatives obtained were used as starting materials for the synthesis of isomeric triazolopyrimidines as well as tetrazolopyrimidines. Furthermore, the rearrangement of triazolopyrimidines

  本文中，我们从3-氧代-4-氰基稠合的吡啶衍生物合成了几种新的环戊基[ c ]吡啶，5,6,7,8-四氢异喹啉和吡喃[3,4- c ]吡啶的肼衍生物。获得的肼基衍生物用作合成异构的三唑并嘧啶和四唑并嘧啶的起始原料。此外，还提出了将三唑并嘧啶7重新排列为三唑并嘧啶8。在DMSO中，四唑并嘧啶10与相关的叠氮嘧啶9处于平衡状态。。通过X射线晶体学证实了四唑并嘧啶的结构。测试合成的化合物的抗微生物活性。
• The azide/tetrazole equilibrium: an investigation in the series of furo- and thieno[2,3-e]tetrazolo[3,2-d]pyrimidine derivatives
  作者：Samvel N. Sirakanyan、Domenico Spinelli、Athina Geronikaki、Viktor G. Kartsev、Henrik A. Panosyan、Armen G. Ayvazyan、Rafael A. Tamazyan、Vincenzo Frenna、Anush A. Hovakimyan

  DOI：10.1016/j.tet.2016.02.048

  日期：2016.4

  excellent yields, which in solution exist in equilibrium with 7(8)-azidofuro(thieno)[3,2-d]pyrimidines 3A and 4A. Compounds 3T/3A and 4T/4A represent useful substrates for investigating the azide/tetrazole equilibrium: it has been examined as a function of solvent, temperature, and their structure. We have observed that, in solution, in both 3 and 4 the equilibrium was strongly affected by the solvent used

  从7（8）-氯呋喃（噻吩并）[3,2- d ]嘧啶1开始，通过与肼反应获得相应的7（8）-肼基呋喃（噻吩并）[3,2- d ]嘧啶2。通过用亚硝酸处理，化合物2以优异的产率得到了熔融的呋喃-和噻吩并[2,3- e ]四唑[1,5- c ]嘧啶3 T和4 T，它们在溶液中与7（8）平衡存在。 -azidofuro（噻吩并）[3,2- d ]嘧啶3甲和4甲。化合物3 T / 3 A和4 T / 4 A代表用于研究叠氮化物/四唑平衡的有用底物：已根据溶剂，温度及其结构进行了检查。我们已经观察到，在溶液中，在3和4中，平衡都受到所用溶剂的强烈影响。相比之下，X射线分析表明噻吩并[2,3- e ] tetrazolo [1,5- c ]嘧啶和呋喃[2,3- e ] tetrazolo [1,5- c固态的嘧啶仅以四唑互变异构形式存在。因此，已经在不同溶剂中计算出了平衡常数和相关的热力学参数：最终观察到一系列（七个）ΔG
• New heterocyclic systems based on 5,6,7,8-tetrahydroisoquinolines
  作者：S. N. Sirakanyan、V. G. Kartsev、A. A. Hovakimyan、A. S. Noravyan、A. A. Shakhatuni

  DOI：10.1007/s10593-013-1192-6

  日期：2013.2

  A method has been developed for the synthesis of new 8-amino-substituted 5-propyl(isobutyl)-1,2,3,4-tetra-hydropyrimido[4',5':4,5]furo[2,3-c]isoquinolines from 3-oxo derivatives of 5,6,7,8-tetra-hydroisoquinolines. Isomeric triazoles, condensed at the edge [c] of the pyrimidine ring, have been obtained from the 8-hydrazino derivatives. A Dimroth rearrangement was carried out in acidic medium.