2-Trimethylsilanyl-5-trimethylsilanyloxymethyl-furan | 120978-37-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-Trimethylsilanyl-5-trimethylsilanyloxymethyl-furan
• 英文别名: Trimethyl-[(5-trimethylsilylfuran-2-yl)methoxy]silane
• CAS: 120978-37-2
• 化学式: C₁₁H₂₂O₂Si₂
• 分子量: 242.465
• InChiKey: UDLOFWZNGQTIAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Trimethylsilanyl-5-trimethylsilanyloxymethyl-furan 以 xylene 为溶剂， 反应 1.0h， 生成 2-Trimethylsilanyl-5-trimethylsilanyloxymethyl-furan-3,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  One pot Synthesis of 3,4-Bis(methoxycarbonyl)-2-trimethylsilylfurans by Diels-Alder Reaction

  摘要：

  DOI：

  10.3987/com-87-4459
• 作为产物：
  描述：

  糠醇 、 三甲基氯硅烷 在 正丁基锂 作用下， 生成 2-Trimethylsilanyl-5-trimethylsilanyloxymethyl-furan
  参考文献：
  名称：

  Intramolecular Diels−Alder Reaction of Furans with Allenyl Ethers Followed by Sulfur and Silicon Atom-Containing Group Rearrangement

  摘要：

  The intramolecular Diels-Alder reactions of a furandiene with an allenyl ether dienophile followed by the alkylthio, alkylsulfinyl, alkylsulfonyl, and trimethylsilyl group rearrangements are reported. Refluxing the propargyl ether 3 with t-BuOK in t-BuOH at 85 degrees C gave the 1,4-rearrangement product 4 exclusively. The alkylthio group 1,4-rearrangement may proceed intramolecularly via the tight; ion pairs. Refluxing the 5-(alkylsulfinyl)-2-furfuryl propargyl ethers 9a-e and the 5-(alkylsulfonyl)-2-furfuryl propargyl ethers 19a-e under the same reaction conditions gave the alkylsulfinyl group and the alkylsulfonyl group 1,2-rearrangement products 10a-e and 20a-e, respectively. No detectable amount of the corresponding 1,4-rearrangement products 11a-e and 21a-e was obtained. In the cases of 9b and 19b, which possess two furfurylic hydrogen atoms, no detectable amount of the furan ring-transfer reaction products was obtained. Refluxing the 5-(trimethylsilyl)-2-furfuryl propargyl ethers 25a-d with t-BuOK in t-BuOH at 85 degrees C for 10 h gave the trimethylsilyl group 1,2-rearrangement products 26a-d and Brook rearrangement products 27a-d. The reaction mechanisms for these novel intramolecular Diels-Alder reactions are discussed. In the case of 37, which possesses two furfurylic hydrogen atoms, compound 38 was obtained via an intramolecular Diels-Alder reaction followed by the furan ring-transfer reaction and Brook rearrangement.

  DOI：

  10.1021/jo980240l