2-nitromorphine | 49751-21-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 2-nitromorphine
• 英文别名: 4,5α-epoxy-17-methyl-2-nitro-morphin-7-ene-3,6α-diol；4,5α-Epoxy-17-methyl-2-nitro-morphin-7-en-3,6α-diol；(4R,4aR,7S,7aR,12bS)-3-methyl-10-nitro-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
• CAS: 49751-21-5
• 化学式: C₁₇H₁₈N₂O₅
• 分子量: 330.34
• InChiKey: FPYOTVBCRPIGNN-AKQBQOJSSA-N

物化性质

• 熔点：
  224 °C
• 沸点：
  491.0±45.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)
• 溶解度：
  溶于丙酮、DCM

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-nitromorphine 在 盐酸 、 tin 、 碘苯二乙酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 2'-(4-hydroxyphenyl)-1',3'-oxazolo-(4',5':2,3)-3-deoxymorphine dihydrochloride
  参考文献：
  名称：

  Synthesis of morphinans with diversely functionalized benzoxazole moieties

  摘要：

  Three independent strategies have been established for the synthesis of morphinans with oxazole moieties derived from the aminophenol function of 2-aminomorphine. All the procedures possess the ability to furnish diversely substituted 2'-oxazole moieties which are considered significant in view of the presented density functional studies on the spatial and electrostatic properties of the proximal functions of the 3-hydroxyl of the morphinan backbone. These data are considered important for neuropharmacological development of potential kappa antagonist morphinans. The second strategy was extended to the direct vinylation of oxazoles to form more complex benzoxazole-type morphinans.

  DOI：

  10.1007/s00706-010-0380-7
• 作为产物：
  描述：

  吗啡 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 2-nitromorphine
  参考文献：
  名称：

  Synthesis of morphinans with diversely functionalized benzoxazole moieties

  摘要：

  Three independent strategies have been established for the synthesis of morphinans with oxazole moieties derived from the aminophenol function of 2-aminomorphine. All the procedures possess the ability to furnish diversely substituted 2'-oxazole moieties which are considered significant in view of the presented density functional studies on the spatial and electrostatic properties of the proximal functions of the 3-hydroxyl of the morphinan backbone. These data are considered important for neuropharmacological development of potential kappa antagonist morphinans. The second strategy was extended to the direct vinylation of oxazoles to form more complex benzoxazole-type morphinans.

  DOI：

  10.1007/s00706-010-0380-7

文献信息

• Wieland; Kappelmeier, Justus Liebigs Annalen der Chemie, 1911, vol. 382, p. 337
  作者：Wieland、Kappelmeier

  DOI：——

  日期：——
• Formation of novel thiazolomorphinans and thiazoloaporphines
  作者：Levente Girán、Sándor Berényi、Attila Sipos

  DOI：10.1016/j.tet.2008.08.069

  日期：2008.11

  A novel strategy has been developed for the synthesis of ring A fused thiazolomorphinans and ring D fused thiazoloaporphines offering the possibility of formation of regioisomeric products. The conventional thermal thiazole-forming reaction was replaced with microwave initiation and a detailed discussion has been presented on the proposed mechanism of the ring Closure. (C) 2008 Elsevier Ltd. All rights reserved.
• Ochiai; Nakamura, Proceedings of the Imperial Academy (Tokyo), vol. 14, p. 134
  作者：Ochiai、Nakamura

  DOI：——

  日期：——