6-Hydroxy-1-(7-trimethylsilanyl-hept-5-ynyl)-1,4,5,6-tetrahydro-pyridine-3,4-dicarboxylic acid dimethyl ester | 141245-21-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 6-Hydroxy-1-(7-trimethylsilanyl-hept-5-ynyl)-1,4,5,6-tetrahydro-pyridine-3,4-dicarboxylic acid dimethyl ester
• CAS: 141245-21-8
• 化学式: C₁₉H₃₁NO₅Si
• 分子量: 381.544
• InChiKey: KLHBLUNMYLJPNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-1-(7-trimethylsilanyl-hept-5-ynyl)-1,4,5,6-tetrahydro-pyridine-3,4-dicarboxylic acid dimethyl 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-2,3-dicarboxylic acid,10-ethenylidene-1,2,6,7,8,9,10,10a-octahydro-, dimethyl ester, trans- 、 Pyrido[1,2-a]azepine-2,3-dicarboxylic acid,10-ethenylidene-1,2,6,7,8,9,10,10a-octahydro-, dimethyl ester, trans-
  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：

  (trimethylsilyl)-1 (tetrahydropyrannyl-2 oxy)-7 heptyne-2 在 sodium azide 、 硫酸 、 水 、 sodium sulfate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 58.0h， 生成 6-Hydroxy-1-(7-trimethylsilanyl-hept-5-ynyl)-1,4,5,6-tetrahydro-pyridine-3,4-dicarboxylic acid dimethyl 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