lupanine N(16)-oxide | 3019-47-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 羽扇豆生物碱
• 英文名称: lupanine N(16)-oxide
• 英文别名: lupanine N-oxide；2-oxosparteine N-oxide；(7S)-(7at,14ac)-dodecahydro-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocin-4-one-12-oxide；(7S)-(7at,14ac)-Dodecahydro-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocin-4-on-12-oxid；(1S,2R,9S,10S)-15-oxido-7-aza-15-azoniatetracyclo[7.7.1.02,7.010,15]heptadecan-6-one
• CAS: 3019-47-4；74183-21-4；74183-22-5；133163-04-9
• 化学式: C₁₅H₂₄N₂O₂
• 分子量: 264.368
• InChiKey: LQMLWHXYFHXGTC-CLDVFSPQSA-N

物化性质

• 熔点：
  76-78 °C(Solv: methanol (67-56-1))

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  lupanine N(16)-oxide 在 硼氘化钠 、 乙酸酐 作用下， 生成 11-β-deutero-α-isolupanine
  参考文献：
  名称：

  Markiewicz, Maria; Wiewiorowski, Maciej, Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1981, vol. 29, # 9-10, p. 407 - 422

  摘要：

  DOI：
• 作为产物：
  描述：

  羽扇豆鹼 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以90%的产率得到lupanine N(16)-oxide
  参考文献：
  名称：

  Probing the metal complexing ability of bis-quinolizidine N-oxides: Synthesis, spectroscopy and crystal structures

  摘要：

  New ZnX2 (X = Cl, Br) complexes with sparteine N1-oxide, sparteine epi-N16-oxide, lupanine (2-oxosparteine) N-oxide and alpha-isosparteine N-oxide were obtained and characterized by spectroscopic and crystallographic methods. Complexation with N1-oxides involves inversion of the configuration at the N16 atom of sparteine, converting its C ring from a boat into a chair form, whereas the structure of sparteine epi-N16-oxide, typified by the trans boat/chair C/D quinolizidine moiety, remains unchanged upon complexation. Coordination of zinc salts in the above compounds is realized solely through the oxygen atom of the N-O group and is accompanied by protonation of the "not-N-oxide" nitrogen atom. At variance lupanine N-oxide forms bis-monodentate complexes with ZnX2 utilizing both the N-oxide and the lactam carbonyl oxygen atoms to bridge the neighboring ZnX2 units, while reaction of alpha-isosparteine N-oxide with ZnX2 leads to formation of complex salts of the general formula [H(-)alpha-Sp(N-oxide)][(ZnX3)(H2O)]. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.05.005

文献信息

• SAITO, KAZUKI;TAKAMATSU, SATOSHI;OHMIYA, SHIGERU;OTOMASU, HIROTAKA;YASUDA+, PHYTOCHEMISTRY, 27,(1988) N 11, C. 3715-3716
  作者：SAITO, KAZUKI、TAKAMATSU, SATOSHI、OHMIYA, SHIGERU、OTOMASU, HIROTAKA、YASUDA+

  DOI：——

  日期：——