bromolupinane | 5176-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: bromolupinane
• 英文别名: bromo-lupinone；Bromo-l-lupinan；1-bromomethylquinolizidine；(9aR)-1t-bromomethyl-(9ar)-octahydro-quinolizin；(9aR)-1t-Brommethyl-(9ar)-octahydro-chinolizin；(1R,9aR)-1-(bromomethyl)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizine
• CAS: 5176-08-9
• 化学式: C₁₀H₁₈BrN
• 分子量: 232.164
• InChiKey: IXSSZPNMLQOZAZ-VHSXEESVSA-N

物化性质

• 熔点：
  111-112 °C(Solv: acetone (67-64-1))
• 沸点：
  104 °C(Press: 1 Torr)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  bromolupinane 在 copper(II) sulfate 作用下， 以 二甲基亚砜 为溶剂， 以81%的产率得到羽扇豆宁
  参考文献：
  名称：

  Syntheses from chiral heterocyclic β-amino esters. A new versatile access to pyrrolizidine and quinolizidine alkaloids

  摘要：

  Chiral heterocyclic P-amino esters can be easily transformed into bicyclic alkaloids after a diastereoselective alkylation followed by specific chemical transformations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00977-7
• 作为产物：
  描述：

  (R)-2-[(R)-1-((S)-1-Phenyl-ethyl)-piperidin-2-yl]-pentane-1,5-diol 在 palladium on activated charcoal 氢气 、 三溴化磷 作用下， 以 甲醇 、 苯 为溶剂， 生成 bromolupinane
  参考文献：
  名称：

  Syntheses from chiral heterocyclic β-amino esters. A new versatile access to pyrrolizidine and quinolizidine alkaloids

  摘要：

  Chiral heterocyclic P-amino esters can be easily transformed into bicyclic alkaloids after a diastereoselective alkylation followed by specific chemical transformations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00977-7

文献信息

• Synthesis of Lupinine Derivatives of Flavonoids
  作者：R. T. Tlegenov、A. Aitmambetov

  DOI：10.1007/s11171-005-0067-8

  日期：2005.9

  The isomerization and oxidative cyclization of 2-hydroxy-4-lupinylchalcones leads to the corresponding 7-lupinylflavanones and 7-lupinylflavones.

  2-羟基-4-羽扇豆基查尔酮的异构化和氧化环化产生相应的7-羽扇豆基黄烷酮和7-羽扇豆基黄酮。
• Novel Quinolizidinyl Derivatives as Antiarrhythmic Agents: 2. Further Investigation
  作者：Bruno Tasso、Roberta Budriesi、Iana Vazzana、Pierfranco Ioan、Matteo Micucci、Federica Novelli、Michele Tonelli、Anna Sparatore、Alberto Chiarini、Fabio Sparatore

  DOI：10.1021/jm100298d

  日期：2010.6.24

  Fifteen quinolizidine derivatives have been tested for antiarrhythmic, inotropic, and chronotropic effects on isolated guinea pig (gp) heart tissues and to assess calcium antagonist activity. All compounds exhibited from moderate to high antiarrhythmic activity, and five of them (3, 4, 6, 13, and 15) were more active and potent than the reference drugs (amiodarone, lidocaine, procainamide, and quinidine). These compounds were studied on spontaneously beating Langendorff-perfuse gp heart; even at concentration 17-67 times higher than the Corresponding EC50 for antiarrhythmic activity, they prolonged the QT intervals only moderately, comparing favorably with amiodarone and quinidine. Compounds 3 and 15 deserve further investigation due to their interesting cardiovascular profiles.
• Clemo; Raper; Tenniswood, Journal of the Chemical Society, 1931, p. 433
  作者：Clemo、Raper、Tenniswood

  DOI：——

  日期：——
• Vazzana; Sparatore; Fadda, Il Farmaco, 1993, vol. 48, # 6, p. 737 - 747
  作者：Vazzana、Sparatore、Fadda、Manca

  DOI：——

  日期：——
• 603. Syntheses from lupinine
  作者：G. R. Clemo、J. Rudinger

  DOI：10.1039/jr9510002714

  日期：——