(–)-2-methylsparteine | 72351-83-8

• 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: (–)-2-methylsparteine
• 英文别名: 2-methylsparteine；2-alpha-Methylsparteine；(1S,2R,6R,9S,10S)-6-methyl-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
• CAS: 72351-83-8
• 化学式: C₁₆H₂₈N₂
• 分子量: 248.412
• InChiKey: FUCFMOLJQDTISP-OLMNGRFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (–)-2-methylsparteine 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以94%的产率得到2-methylsparteine N(16)-oxide
  参考文献：
  名称：

  Conformation of some sparteine N-16 oxides revisited

  摘要：

  Sparteine N-16 oxides were thought to occur in all chair conformations with cis fusion between their C and D rings. NMR spectral analysis made possible indication of the chair-chair-boat-chair form with cis fassion of C, D rings for sparteine, 2-phenyl- and 2-methylsparteine N-16 oxides. Molecular energy found by means of DFT, Hartree-Fock, AM1, PM3 methods supported this new shape of bisquinolizidine skeleton. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(02)00124-2
• 作为产物：
  描述：

  2-methyl-2-dehydrosparteine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以1.03 g的产率得到(–)-2-methylsparteine
  参考文献：
  名称：

  Boczon, Wladyslaw, Polish Journal of Chemistry, 1981, vol. 55, # 2, p. 339 - 351

  摘要：

  DOI：
• 作为试剂：
  描述：

  6,7-二甲氧基-3,4-二氢异喹啉 、 2,2-dimethyl-3-(o-toluoyl)oxazolidine 在 正丁基锂 、 (–)-2-methylsparteine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.42h， 以51%的产率得到2,3-dimethoxy-8-oxoberbine
  参考文献：
  名称：

  Asymmetric Synthesis of 2,3-Dimethoxy-8-oxoberbine, Precursor of O-Methylbharatamine

  摘要：

  DOI：

  10.3987/com-18-s(f)73

文献信息

• Synthesis and Structure of New N-Bromobenzyl Bis-quinolizidine Derivatives
  作者：Beata Jasiewicz、Karolina Malczewska-Jaskola、Katarzyna Polom

  DOI：10.2174/157017812802139672

  日期：2012.7.1

  New potentially biologically active N-bromobenzyl derivatives of α-isosparteine and 2-methylsparteine were obtained. Newly obtained compounds were characterized by IR and NMR spectroscopy. The structure of the new compounds in solution was proposed

  获得了具有潜在生物活性的α-异天冬氨酸和 2-甲基天冬氨酸的 N-溴苄基新衍生物。通过红外光谱和核磁共振光谱对新化合物进行了表征。提出了新化合物在溶液中的结构
• Synthesis and crystal structures of iron(II) dichloride complexes with α-isosparteine, β-isosparteine and 2-methylsparteine
  作者：Beata Jasiewicz、Takanori Inazumi、Yoshiyuki Inagaki、Yuko Wasada-Tsutsui、Yasuhiro Funahashi、Hideki Masuda

  DOI：10.1016/j.molstruc.2010.09.024

  日期：2010.12

  Tetrahedrally distorted complexes of alpha-isosparteine, beta-isosparteine and 2-methylsparteine with FeCl2 have been synthesised. Crystal structures of these complexes are reported and compared with the structure of (-)-sparteine analogue. Coordination to Fe(II) center in beta-isosparteine and 2-methylsparteine brings about an inversion at the N16 nitrogen and change in configuration at the ring junction from trans to cis, accompanied by a change in the C-ring conformation from boat to chair. The all-chair alpha-isosparteine skeleton remains unchanged upon complexation. Structural parameters of the complexes are investigated using Becke three-parameter hybrid exchange functional combined with the Lee-Yang-Parr correlation functional (B3LYP) with 6-31G and 6-311G basis sets applied for geometry optimizations. (C) 2010 Elsevier B.V. All rights reserved.