4-Cyano-6-hydroxy-1-(7-trimethylsilanyl-hept-5-ynyl)-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester | 141245-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-Cyano-6-hydroxy-1-(7-trimethylsilanyl-hept-5-ynyl)-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
• CAS: 141245-23-0
• 化学式: C₁₈H₂₈N₂O₃Si
• 分子量: 348.517
• InChiKey: JAUAGHRLAIJLGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  73.56
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-Cyano-6-hydroxy-1-(7-trimethylsilanyl-hept-5-ynyl)-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 Pyrido[1,2-a]azepine-3-carboxylic acid,2-cyano-10-ethenylidene-1,2,6,7,8,9,10,10a-octahydro-, methyl ester,cis- 、
  参考文献：
  名称：

  Stereoselective sequential photochemical cycloaddition - iminium ion - propargylsilane cyclization. Synthesis of quinolizidines and pyrido [1,2-a]azepines

  摘要：

  Photochemical cycloaddition of the enaminecarbaldehydes 15 and 16 with the acrylic acid derivatives 20a-c gave the 2-hydroxytetrahydropyridines 21a-c and 24a-c, respectively which cyclize on treatment with trifluoroacetic acid or Lewis acids to furnish the quinolizidines 22a-c and pyrido[1,2-a]azepines 25a-c, respectively in good yields and with high 1,3-induced diastereoselectivity. Indolizidines 27 cannot be prepared by this method.

  DOI：

  10.1016/s0040-4020(01)88876-1
• 作为产物：
  描述：

  在 sodium azide 、 水 、 sodium sulfate 、 三苯基膦 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 41.0h， 生成 4-Cyano-6-hydroxy-1-(7-trimethylsilanyl-hept-5-ynyl)-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselective sequential photochemical cycloaddition - iminium ion - propargylsilane cyclization. Synthesis of quinolizidines and pyrido [1,2-a]azepines

  摘要：

  Photochemical cycloaddition of the enaminecarbaldehydes 15 and 16 with the acrylic acid derivatives 20a-c gave the 2-hydroxytetrahydropyridines 21a-c and 24a-c, respectively which cyclize on treatment with trifluoroacetic acid or Lewis acids to furnish the quinolizidines 22a-c and pyrido[1,2-a]azepines 25a-c, respectively in good yields and with high 1,3-induced diastereoselectivity. Indolizidines 27 cannot be prepared by this method.

  DOI：

  10.1016/s0040-4020(01)88876-1