6-Azido-1-trimethylsilyl-2-hexyne | 125763-99-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-Azido-1-trimethylsilyl-2-hexyne
• 英文别名: 6-Azidohex-2-ynyl(trimethyl)silane
• CAS: 125763-99-7
• 化学式: C₉H₁₇N₃Si
• 分子量: 195.34
• InChiKey: XJSGVHXPRWXDIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Azido-1-trimethylsilyl-2-hexyne 在 水 、 sodium sulfate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 Methyl 2-Formyl-3-(6-trimethylsilyl-4-hexynyl-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
• 作为产物：
  描述：

  2-(4-戊炔氧基)四氢-2H-吡喃 在 正丁基锂 、 sodium azide 、 硫酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 37.5h， 生成 6-Azido-1-trimethylsilyl-2-hexyne
  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

• The chemistry of vicinal tricarbonyls. New routes to indolizidines
  作者：Harry H. Wasserman、Jan D. Cook、Chi B. Vu

  DOI：10.1021/jo00293a005

  日期：1990.3
• Intramolecular reactions of acyclic N-acyliminium ions I propargyl silanes as nucleophiles
  作者：Henk Hiemstra、Hendrikus P. Fortgens、Sander Stegenga、W.Nico Speckamp

  DOI：10.1016/s0040-4039(00)98643-x

  日期：1985.1
• 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.