11-nitro-10-hydroxyquinine | 1374025-81-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: 11-nitro-10-hydroxyquinine
• 英文别名: 1-[(3R,4S,6S)-6-[(R)-hydroxy-(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-yl]-2-nitroethanol
• CAS: 1374025-81-6
• 化学式: C₂₀H₂₅N₃O₅
• 分子量: 387.436
• InChiKey: OESRHUAMMQRSNO-JXKHBUDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  11-nitro-10-hydroxyquinine 、 乙醛 在 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以47%的产率得到2-(ethylamino)-1-[(3R,4S,6S)-6-[(R)-hydroxy-(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-yl]ethanol
  参考文献：
  名称：

  Reductive N-Alkylation of Nitroarenes: A Green Approach for the N-Alkylation of Natural Products

  摘要：

  A simple, mild, cost-effective, and green approach for the reductive mono-N-alkylation of nitroarenes has been developed. HOAc/Zn are utilized as the reducing system together with a carbonyl compound as an alkyl source in methanol. Excellent yields were obtained with stoichiometric control of mono- over dialkylated products. Application to five complex natural products demonstrated the practical utility of the method.

  DOI：

  10.1021/jo300303d
• 作为产物：
  描述：

  奎宁 在 硝酸 、 溶剂黄146 作用下， 反应 1.0h， 以53%的产率得到11-nitro-10-hydroxyquinine
  参考文献：
  名称：

  Reductive N-Alkylation of Nitroarenes: A Green Approach for the N-Alkylation of Natural Products

  摘要：

  A simple, mild, cost-effective, and green approach for the reductive mono-N-alkylation of nitroarenes has been developed. HOAc/Zn are utilized as the reducing system together with a carbonyl compound as an alkyl source in methanol. Excellent yields were obtained with stoichiometric control of mono- over dialkylated products. Application to five complex natural products demonstrated the practical utility of the method.

  DOI：

  10.1021/jo300303d

文献信息

• Reductive <i>N</i>-Alkylation of Nitroarenes: A Green Approach for the <i>N</i>-Alkylation of Natural Products
  作者：Amir E. Wahba、Mark T. Hamann

  DOI：10.1021/jo300303d

  日期：2012.5.18

  A simple, mild, cost-effective, and green approach for the reductive mono-N-alkylation of nitroarenes has been developed. HOAc/Zn are utilized as the reducing system together with a carbonyl compound as an alkyl source in methanol. Excellent yields were obtained with stoichiometric control of mono- over dialkylated products. Application to five complex natural products demonstrated the practical utility of the method.