5a-methyl-5,6,7,8,9,11-hexahydro-5aH-pyrido[2,1-b]quinazolin-9-one | 1242265-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5a-methyl-5,6,7,8,9,11-hexahydro-5aH-pyrido[2,1-b]quinazolin-9-one
• 英文别名: 5a-methyl-5,5a,6,7,8,11-hexahydro-pyrido[2,1-b]quinazolin-9-one；5a-methyl-6,7,8,11-tetrahydro-5H-pyrido[2,1-b]quinazolin-9-one
• CAS: 1242265-48-0
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: VRZFXVNLMHTDHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氧代己酸 、 2-氨基苄胺 以 乙醇 、 水 为溶剂， 反应 16.0h， 以73%的产率得到5a-methyl-5,6,7,8,9,11-hexahydro-5aH-pyrido[2,1-b]quinazolin-9-one
  参考文献：
  名称：

  微环平行合成双环内酰胺的水基条件

  摘要：

  我们报告了有效的小型化条件，以准备用于筛选的双环内酰胺阵列。溶剂的性质通常是反应性的重要因素。在小的合成规模下，当需要自动移液装置时，溶剂的物理性质（例如表面张力和蒸气压）也变得非常重要。在证明试剂在水中或乙醇和水的混合物中完全蒸发会产生预期的内酰胺后，我们以制备80个成员的文库为例，说明了反应和过程。我们的合成方案经验证可用于1到100 mg的合成规模。因此，它既可用于生产HTS的快速测试样品，又可用于制备中间体，用于合成更多复杂的，受自然界启发的化合物。

  DOI：

  10.1016/j.tetlet.2012.11.082

文献信息

• Au(I)-Catalyzed Cascade Reaction Involving Formal Double Hydroamination of Alkynes Bearing Tethered Carboxylic Groups: An Easy Access to Fused Dihydrobenzimidazoles and Tetrahydroquinazolines
  作者：Nitin T. Patil、Anil Kumar Mutyala、Pediredla G. V. V. Lakshmi、Balakrishna Gajula、Balasubramanian Sridhar、Gurava Reddy Pottireddygari、Tadikamalla Prabhakar Rao

  DOI：10.1021/jo1013228

  日期：2010.9.3

  A process involving gold(I)-catalyzed formal double hydroamination of alkynes, bearing a tethered carboxylic group, for the synthesis of fused dihydrobenzimidazoles and tetrahydroquinazolines has been developed. A series of transition metal catalysts have been screened for this transformation, and a catalyst system consisting of Ph3PAuCl (1 mol %) and AgOTf (1 mol %) was found to be the best. The procedure entails the reaction of easily accessible starting materials such as alkynoic acids and 1,2-diaminobenzenes/2-aminobenzylamines in the presence of the catalyst in 1,2-dichloroethane at 100 degrees C. In the case of alpha-substituted alkynoic acids, the corresponding products were obtained in high diastereoselectivities; the structure of the diastereomers has been unambiguously characterized by NMR techniques. The mechanism of the reaction is discussed, and the origin of the diastereoselectivities is addressed. It was observed that under the microwave irradiation conditions, the reaction time is significantly shortened (0.5 h).