3-methoxytrimethylsilyloxybutadiene | 138118-31-7

• 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: 3-methoxytrimethylsilyloxybutadiene
• 英文别名: Danishefsky diene；[(1E)-3-methoxybuta-1,3-dienoxy]-trimethylsilane
• CAS: 138118-31-7
• 化学式: C₈H₁₆O₂Si
• 分子量: 172.299
• InChiKey: JACLFCGZHCIJSZ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxytrimethylsilyloxybutadiene 、 氧气 以28%的产率得到
  参考文献：
  名称：

  CLENNAN, E. L.;LESPERANCE, R. P., TETRAHEDRON LETT., 1983, 24, N 40, 4291-4294

  摘要：

  DOI：

文献信息

• Synthesis and Application of the First Chiral and Highly Lewis Acidic Silyl Cationic Catalyst
  作者：Mogens Johannsen、Karl Anker Jørgensen、Günter Helmchen

  DOI：10.1021/ja981021k

  日期：1998.8.1

  Center for Metal Catalyzed ReactionsDepartment of Chemistry, Aarhus UniVersityDK-8000 Aarhus C, DenmarkOrganisch-Chemisches Institut der UniVersita¨tIm Neuenheimer Feld 270, D-69120 Heidelberg, GermanyReceiVed March 26, 1998Recently, great progress has been made in the field of silyliumchemistry and it seems possible to prepare the long-desired siliconcation in condensed phase.

  Center for Metal Catalyzed ReactionsDepartment of Chemistry, Aarhus UniVersityDK-8000 Aarhus C, DenmarkOrganisch-Chemisches Institut der UniVersita–Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany 199 年 3 月 26 日，化学领域取得了巨大进展似乎可以在凝聚相中制备长期需要的硅阳离子。
• Diastereoselective diels-alder reactions between substituted 1,3-butadienes and n-α-methylbenzylmaleimide
  作者：S.W. Baldwin、P. Greenspan、C. Alaimo、A.T. McPhail

  DOI：10.1016/s0040-4039(00)79415-9

  日期：1991.10

  The TiCl4 catalyzed reaction between 2-t-butyl-1,3-butadiene and N-alpha-methylbenzylmaleimide at -65-degrees-C affords diastereomeric Diels-Alder adducts in a 15:1 ratio. The structure of the major adduct was determined by x-ray.
• Addition reactions to chiral aziridine-2-carboxaldimine toward various enantiopure nitrogen-containing heterocycles
  作者：Heui-Yoon Noh、Sang-Woo Kim、Seong In Paek、Hyun-Joon Ha、Hoseop Yun、Won Koo Lee

  DOI：10.1016/j.tet.2005.07.064

  日期：2005.9

  Chiral (2R,1'R)-(1'-phenylethyl)aziridine-2-carboxaldimine was utilized as a nitrogen-containing starting substrate for the preparation of various enantiopure nitrogen-containing heterocycles. The additions of nucleophiles including organomagnesium reagents, cyanotrimethyl si lane and ketene acetal to the chiral (2R,1'R)-(1'-phenylethyl)aziridine-2-carboxaldimine proceeded in highly stereoselective manner via chelation controlled transition states. Subsequent treatment of adducts with triphosgene and NaH yielded 5-substituted-4-chloromethylimidazolidin-2-ones. This imine was also served as either aza-diene or aza-dienophile with olefin or diene to provide hetero-Diels-Alder adducts 2-aziridinylpiperidines or 1,2,3,4-tetrahydroquinolines. (c) 2005 Elsevier Ltd. All rights reserved.