9-amino(9-deoxy)dihydroquinidine | 780034-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-amino(9-deoxy)dihydroquinidine
• 英文别名: (S)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanamine
• CAS: 780034-75-5
• 化学式: C₂₀H₂₇N₃O
• 分子量: 325.454
• InChiKey: HGVZOZLENNRYCV-LHHVKLHASA-N

物化性质

• 沸点：
  487.5±30.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  51.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-amino(9-deoxy)dihydroquinidine 、 3-甲氧基异硫氰酸苯酯 以 四氢呋喃 为溶剂， 反应 12.0h， 以72%的产率得到
  参考文献：
  名称：

  Quinine-Derived Thiourea and Squaramide Catalyzed Conjugate Addition of α-Nitrophosphonates to Enones: Asymmetric Synthesis of Quaternary α-Aminophosphonates

  摘要：

  Conjugate addition of a-nitrophosphonates to enones was carried out in the presence of two sets of organocatalysts, viz. a quinine-thiourea and a quinine-squaramide. The quinine-thiourea provided the products possessing an a-quaternary chiral center in high enantioselectivities only in the case of electron rich enones. On the other hand, the quinine-squaramide was more efficient in that a wide variety of electron rich and electron poor enones underwent Michael addition of nitrophosphonates to afford the quaternary a-nitrophosphonates in excellent yields and enantioselectivities. The hydrogen bonding donor ability of the bifunctional catalyst, as shown in the proposed transition states, appears primarily responsible for the observed selectivity. However, a favorable p-stacking between the aryl groups of thiourea/squaramide and aryl vinyl ketone also appeared favorable. The reaction was amenable to scale up, and the enantioenriched quaternary a-nitrophosphonates could be easily transformed to synthetically and biologically useful quaternary a-aminophosphonates and other multifunctional molecules.

  DOI：

  10.1021/jo502332r
• 作为试剂：
  描述：

  苯并咪唑 、 乙酸乙烯酯 在 9-amino(9-deoxy)dihydroquinidine 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以96%的产率得到1-(benzimidazol-1-yl)ethyl acetate
  参考文献：
  名称：

  金鸡纳衍生物可作为可持续和可回收的均相有机催化剂，用于添加Aza-Markovnikov †

  摘要：

  三种金鸡纳衍生物已显示出显着的活性，可催化N-杂环对乙烯基酯的氮杂-马尔可夫尼科夫加成反应。彻底优化了具有有价值的生物活性的氮杂-马尔可夫尼科夫加合物的合成。通过研究原料，碱和溶剂的比例，我们获得了一种新的有效方法，可以在温和条件下用少量过量的乙烯基酯进行操作，从而提供具有优异收率和高区域选择性的产品。该优化使反应的谢尔顿E因子降低了42％。此外，评估了用于催化剂再循环的膜分离以进一步提高合成的可持续性。

  DOI：

  10.1039/c8nj01277f

文献信息

• Quinine-Derived Thiourea and Squaramide Catalyzed Conjugate Addition of α-Nitrophosphonates to Enones: Asymmetric Synthesis of Quaternary α-Aminophosphonates
  作者：Kalisankar Bera、Irishi N. N. Namboothiri

  DOI：10.1021/jo502332r

  日期：2015.2.6

  Conjugate addition of a-nitrophosphonates to enones was carried out in the presence of two sets of organocatalysts, viz. a quinine-thiourea and a quinine-squaramide. The quinine-thiourea provided the products possessing an a-quaternary chiral center in high enantioselectivities only in the case of electron rich enones. On the other hand, the quinine-squaramide was more efficient in that a wide variety of electron rich and electron poor enones underwent Michael addition of nitrophosphonates to afford the quaternary a-nitrophosphonates in excellent yields and enantioselectivities. The hydrogen bonding donor ability of the bifunctional catalyst, as shown in the proposed transition states, appears primarily responsible for the observed selectivity. However, a favorable p-stacking between the aryl groups of thiourea/squaramide and aryl vinyl ketone also appeared favorable. The reaction was amenable to scale up, and the enantioenriched quaternary a-nitrophosphonates could be easily transformed to synthetically and biologically useful quaternary a-aminophosphonates and other multifunctional molecules.