(1R,9S)-11-butyryl-7,11-diazatricyclo[7.3.1.0^2,7]trideca-2,4-dien-6-one

• 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: (1R,9S)-11-butyryl-7,11-diazatricyclo[7.3.1.0^2,7]trideca-2,4-dien-6-one
• 英文别名: (1R,9S)-11-butanoyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: QABVKJWEQZBVIK-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,9S)-11-butyryl-7,11-diazatricyclo[7.3.1.0^2,7]trideca-2,4-dien-6-one 在 platinum(IV) oxide 氢气 、 lithium aluminium tetrahydride 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 40.0h， 以81%的产率得到(1R,2S,9S)-11-(n-butyl)-7,11-diazatricyclo[7.3.1.0^2,7]tridecane
  参考文献：
  名称：

  Evaluation of (+)-Sparteine-like Diamines for Asymmetric Synthesis

  摘要：

  Three new (+)-sparteine-like diamines were prepared from (-)-cytisine and evaluated as sparteine surrogates in the alpha-lithiation rearrangement of cyclooctene oxide and the palladium(II)/diamine catalyzed oxidative kinetic resolution of I-indanol. The new diamines exhibited opposite enantioselectivity to that observed with (-)-sparteine but increasing the steric hindrance of the N-alkyl group beyond N-Et had a detrimental effect on enantioselectivity. The optimal N-Me diamine was evaluated with much success in five other (-)-sparteine-mediated processes involving different metals (lithium, magnesium, and copper) and different types of reaction mechanisms.

  DOI：

  10.1021/jo049182w
• 作为产物：
  描述：

  丁酰氯 、 cytisine 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 以84%的产率得到(1R,9S)-11-butyryl-7,11-diazatricyclo[7.3.1.0^2,7]trideca-2,4-dien-6-one
  参考文献：
  名称：

  Evaluation of (+)-Sparteine-like Diamines for Asymmetric Synthesis

  摘要：

  Three new (+)-sparteine-like diamines were prepared from (-)-cytisine and evaluated as sparteine surrogates in the alpha-lithiation rearrangement of cyclooctene oxide and the palladium(II)/diamine catalyzed oxidative kinetic resolution of I-indanol. The new diamines exhibited opposite enantioselectivity to that observed with (-)-sparteine but increasing the steric hindrance of the N-alkyl group beyond N-Et had a detrimental effect on enantioselectivity. The optimal N-Me diamine was evaluated with much success in five other (-)-sparteine-mediated processes involving different metals (lithium, magnesium, and copper) and different types of reaction mechanisms.

  DOI：

  10.1021/jo049182w

文献信息

• Evaluation of (+)-Sparteine-like Diamines for Asymmetric Synthesis
  作者：Michael J. Dearden、Matthew J. McGrath、Peter O'Brien

  DOI：10.1021/jo049182w

  日期：2004.8.1

  Three new (+)-sparteine-like diamines were prepared from (-)-cytisine and evaluated as sparteine surrogates in the alpha-lithiation rearrangement of cyclooctene oxide and the palladium(II)/diamine catalyzed oxidative kinetic resolution of I-indanol. The new diamines exhibited opposite enantioselectivity to that observed with (-)-sparteine but increasing the steric hindrance of the N-alkyl group beyond N-Et had a detrimental effect on enantioselectivity. The optimal N-Me diamine was evaluated with much success in five other (-)-sparteine-mediated processes involving different metals (lithium, magnesium, and copper) and different types of reaction mechanisms.