4,5-二氢-1H-[1,2,4]恶二唑并[4,3-a]喹喔啉-1-酮 | 36002-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 4,5-二氢-1H-[1,2,4]恶二唑并[4,3-a]喹喔啉-1-酮
• 英文名称: 4,5-dihydro[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one
• 英文别名: 4,5-dihydro-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one；1-Oxo-4,5-dihydro-<1.2.4>oxadiazolo<4.3-a>chinoxalin；4,5-Dihydro-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one
• CAS: 36002-67-2
• 化学式: C₉H₇N₃O₂
• mdl: MFCD18806897
• 分子量: 189.173
• InChiKey: ZFNNEMYZHFPQCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  53.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4,5-二氢-1H-[1,2,4]恶二唑并[4,3-a]喹喔啉-1-酮 在 potassium permanganate 作用下， 以 乙腈 为溶剂， 以88%的产率得到1H-[1,2,4]恶草灵并[4,3-a]喹喔啉-1-酮
  参考文献：
  名称：

  Suzuki–Miyaura reactions of the soluble guanylate cyclase inhibitor NS2028: a non-product specific route to C-8 substituted analogues

  摘要：

  Both soluble guanylate cyclase (sGC) inhibitors ODQ 1 and NS2028 2 are synthesized via improved protocols. In the former case treating 3,4-dihydroquinoxalin-2(1H)-one oxime 8, which can be prepared in two steps from 1,2-benzenediamine, with 1,1'-carbonyldiimidazole (CDI) gives the dihydro-ODQ 10 that in the presence of KMnO4 oxidises to give ODQ 1 in an overall yield of 46% starting from 1,2-benzenediamine. In the latter case, the synthesis affords NS2028 2 from 2-amino-4-bromophenol 3 in three steps with an overall yield of 85% and avoids the need for chromatography. Furthermore, Suzuki-Miyaura reaction conditions are described that enable the preparation of 8-aryl and 8-heteroaryl derivatives of NS2028 directly from NS2028 2. Finally, demethylation of the 8-(methoxyphenyl) substituted analogues afforded the 8-(hydroxyphenyl) derivatives 40-42. All new products are fully characterised. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.003
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 2-Oximino-1,2,3,4-tetrahydro-chinoxalin 以 四氢呋喃 为溶剂， 反应 5.0h， 以67%的产率得到4,5-二氢-1H-[1,2,4]恶二唑并[4,3-a]喹喔啉-1-酮
  参考文献：
  名称：

  Suzuki–Miyaura reactions of the soluble guanylate cyclase inhibitor NS2028: a non-product specific route to C-8 substituted analogues

  摘要：

  Both soluble guanylate cyclase (sGC) inhibitors ODQ 1 and NS2028 2 are synthesized via improved protocols. In the former case treating 3,4-dihydroquinoxalin-2(1H)-one oxime 8, which can be prepared in two steps from 1,2-benzenediamine, with 1,1'-carbonyldiimidazole (CDI) gives the dihydro-ODQ 10 that in the presence of KMnO4 oxidises to give ODQ 1 in an overall yield of 46% starting from 1,2-benzenediamine. In the latter case, the synthesis affords NS2028 2 from 2-amino-4-bromophenol 3 in three steps with an overall yield of 85% and avoids the need for chromatography. Furthermore, Suzuki-Miyaura reaction conditions are described that enable the preparation of 8-aryl and 8-heteroaryl derivatives of NS2028 directly from NS2028 2. Finally, demethylation of the 8-(methoxyphenyl) substituted analogues afforded the 8-(hydroxyphenyl) derivatives 40-42. All new products are fully characterised. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.003

文献信息

• Harsanyi,K. et al., Chemische Berichte, 1972, vol. 105, p. 805 - 812
  作者：Harsanyi,K. et al.

  DOI：——

  日期：——
• Harsanyi,K. et al., Justus Liebigs Annalen der Chemie, 1973, p. 190 - 194
  作者：Harsanyi,K. et al.

  DOI：——

  日期：——
• Suzuki–Miyaura reactions of the soluble guanylate cyclase inhibitor NS2028: a non-product specific route to C-8 substituted analogues
  作者：Andrey A. Berezin、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2011.04.003

  日期：2011.6

  Both soluble guanylate cyclase (sGC) inhibitors ODQ 1 and NS2028 2 are synthesized via improved protocols. In the former case treating 3,4-dihydroquinoxalin-2(1H)-one oxime 8, which can be prepared in two steps from 1,2-benzenediamine, with 1,1'-carbonyldiimidazole (CDI) gives the dihydro-ODQ 10 that in the presence of KMnO4 oxidises to give ODQ 1 in an overall yield of 46% starting from 1,2-benzenediamine. In the latter case, the synthesis affords NS2028 2 from 2-amino-4-bromophenol 3 in three steps with an overall yield of 85% and avoids the need for chromatography. Furthermore, Suzuki-Miyaura reaction conditions are described that enable the preparation of 8-aryl and 8-heteroaryl derivatives of NS2028 directly from NS2028 2. Finally, demethylation of the 8-(methoxyphenyl) substituted analogues afforded the 8-(hydroxyphenyl) derivatives 40-42. All new products are fully characterised. (C) 2011 Elsevier Ltd. All rights reserved.