Methyl 2-Formyl-3-(7-trimethylsilyl-5-heptynyl-1-amino)-2-propenoate | 141245-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-Formyl-3-(7-trimethylsilyl-5-heptynyl-1-amino)-2-propenoate
• 英文别名: methyl 2-formyl-3-(7-trimethylsilylhept-5-ynylamino)prop-2-enoate
• CAS: 141245-16-1
• 化学式: C₁₅H₂₅NO₃Si
• 分子量: 295.454
• InChiKey: WOSVMJHBMJJETC-UHFFFAOYSA-N

物化性质

• 沸点：
  449.0±45.0 °C(Predicted)
• 密度：
  0.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methyl 2-Formyl-3-(7-trimethylsilyl-5-heptynyl-1-amino)-2-propenoate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 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-
  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：

  7-(Trimethylsilyl)-5-heptyn-1-ol 在 sodium azide 、 水 、 sodium sulfate 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 Methyl 2-Formyl-3-(7-trimethylsilyl-5-heptynyl-1-amino)-2-propenoate
  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

文献信息

• Stereoselective sequential photochemical cycloaddition - iminium ion - propargylsilane cyclization. Synthesis of quinolizidines and pyrido [1,2-a]azepines
  作者：Lutz F. Tietze、Josef R. Wünsch、Mathias Noltemeyer

  DOI：10.1016/s0040-4020(01)88876-1

  日期：1992.1

  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.