1-hydroxy-1-(hydroxymethyl)-3-trimethylsilyl-7,8,9,9a-tetrahydro-6H-quinolizin-4-one | 916067-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: 1-hydroxy-1-(hydroxymethyl)-3-trimethylsilyl-7,8,9,9a-tetrahydro-6H-quinolizin-4-one
• CAS: 916067-59-9
• 化学式: C₁₃H₂₃NO₃Si
• 分子量: 269.416
• InChiKey: DXYVOWCWZALQRM-UHFFFAOYSA-N

物化性质

• 沸点：
  430.1±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hydroxy-1-(hydroxymethyl)-3-trimethylsilyl-7,8,9,9a-tetrahydro-6H-quinolizin-4-one 在 platinum(IV) oxide 氢气 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、517.11 kPa 条件下， 反应 19.0h， 生成 (1R,9aR)-1-(2-trimethylsilylethoxymethyl)-1,2,3,6,7,8,9,9a-octahydroquinolizin-4-one
  参考文献：
  名称：

  Synthesis of δ-thiolactams by the aza-Diels–Alder reaction of in situ generated allenyltrimethylsilylthioketenes with imines

  摘要：

  Allenyltrimethylsilylthioketenes, generated in situ through [3,3] sigmatropic rearrangement of trimethylsilylethynyl propargyl sulfides, underwent facile [4+2] cycloaddition with imines to afford the corresponding delta-thiolactams. The resulting 2-trimethylsilyl-4-methylenetetrahydroquinolidine-2-thione, obtained by the [4+2] cycloaddition using piperideine as a dienophile, was transformed into (+/-)-lupinine in six steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.104
• 作为产物：
  描述：

  2,3,4,5-四氢吡啶 在 四氧化锇 、 正丁基锂 、 N-甲基吲哚酮 、 sulfur 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 氯仿 、 水 为溶剂， 反应 24.5h， 生成 1-hydroxy-1-(hydroxymethyl)-3-trimethylsilyl-7,8,9,9a-tetrahydro-6H-quinolizin-4-one
  参考文献：
  名称：

  Synthesis of δ-thiolactams by the aza-Diels–Alder reaction of in situ generated allenyltrimethylsilylthioketenes with imines

  摘要：

  Allenyltrimethylsilylthioketenes, generated in situ through [3,3] sigmatropic rearrangement of trimethylsilylethynyl propargyl sulfides, underwent facile [4+2] cycloaddition with imines to afford the corresponding delta-thiolactams. The resulting 2-trimethylsilyl-4-methylenetetrahydroquinolidine-2-thione, obtained by the [4+2] cycloaddition using piperideine as a dienophile, was transformed into (+/-)-lupinine in six steps. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.104

文献信息

• Synthesis of δ-thiolactams by the aza-Diels–Alder reaction of in situ generated allenyltrimethylsilylthioketenes with imines
  作者：Shigenobu Aoyagi、Michiko Hakoishi、Mariko Suzuki、Yusuke Nakanoya、Kazuaki Shimada、Yuji Takikawa

  DOI：10.1016/j.tetlet.2006.08.104

  日期：2006.10

  Allenyltrimethylsilylthioketenes, generated in situ through [3,3] sigmatropic rearrangement of trimethylsilylethynyl propargyl sulfides, underwent facile [4+2] cycloaddition with imines to afford the corresponding delta-thiolactams. The resulting 2-trimethylsilyl-4-methylenetetrahydroquinolidine-2-thione, obtained by the [4+2] cycloaddition using piperideine as a dienophile, was transformed into (+/-)-lupinine in six steps. (c) 2006 Elsevier Ltd. All rights reserved.