1,3-diethoxy-1-trimethylsilyloxy-1,3-butadiene

• 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: 1,3-diethoxy-1-trimethylsilyloxy-1,3-butadiene
• 英文别名: Brassard's diene；1,3-diethoxy-1-trimethylsiloxybuta-1,3-diene；1,3-Diethoxy-1-trimethylsiloxybuta-1,3-diene；1,3-diethoxybuta-1,3-dienoxy(trimethyl)silane
• 化学式: C₁₁H₂₂O₃Si
• 分子量: 230.379
• InChiKey: VHHCTVQSTNKXIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-diethoxy-1-trimethylsilyloxy-1,3-butadiene 在 potassium carbonate 、 苯硫酚 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 11.0h， 生成 2-(4-chlorophenyl)-4-ethoxy-2,3-dihydro-1H-pyridin-6-one
  参考文献：
  名称：

  A New Synthesis of Dihydropyridin-2-ones from Brassard’s Diene and Imines

  摘要：

  A new method for the synthesis of dihydropyridin-2-ones from various N-2-nitrobenzenesulfonyl (nosyl) imines and 1,3-diethoxy-1-trimethylsiloxy-1,3-butadiene (Brassard's diene) under weakly-basic conditions is described. This synthesis of dihydropyridin-2-ones involves the initial addition reaction of Brassard's diene to imines to afford the adducts followed by a cyclization reaction that forms the corresponding 4-ethoxy-5,6-dihydro-1H-pyridin-2-ones in moderate to good yields after deprotection of its nosyl group from the adducts.

  DOI：

  10.3987/com-08-s(n)51

文献信息

• CHEMICAL PROCESS
  申请人：LENGER Steven Robert

  公开号：US20080188657A1

  公开（公告）日：2008-08-07

  A process for the manufacture of a compound of formula (V), useful for making rosuvastatin, by a stereoselective aldol reaction is described.

  本发明描述了一种用于制备化合物(V)的方法，该化合物可用于制备罗伊司他汀，该方法通过立体选择性的Aldol反应进行。
• WO2008/65410
  申请人：——

  公开号：——

  公开（公告）日：——
• Hetero Diels–Alder reactions of acyl phosphonates: synthesis of glycosyl type phosphonates
  作者：Sidika Polat-Cakir、Ayhan S. Demir

  DOI：10.1016/j.tet.2011.02.007

  日期：2011.4

  We have prepared glycosyl type phosphonates via hetero Diels-Alder (HDA) reactions of acyl phosphonates with electron rich dienes. HDA reactions of acyl phosphonates with Danishefsky's diene required thermal activation to yield the desired dihydropyranones in good yield (70-91%). The reactions with Brassard's diene involved Lewis acid promotion to yield the corresponding lactones, though in moderate yield (33-69%). (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of functionalized 2-alkoxybenzoates, 2-aryloxybenzoates and xanthones based on formal [3+3] cyclocondensations of 3-alkoxy- and 3-aryloxy-1-silyloxy-1,3-butadienes with 3-silyloxy-2-en-1-ones
  作者：Gerson Mroß、Helmut Reinke、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2009.02.052

  日期：2009.5

  Functionalized 2-alkoxy- and 2-aryloxybenzoates were prepared by formal [3+3] cyclocondensations of 3-alkoxy- and 3-aryloxy-1-silyloxy-1,3-butadienes with 3-silyloxy-2-en-1-ones. The reaction of 2-aryloxybenzoates with concentrated sulfuric acid resulted in the formation of xanthones. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of functionalized arylalkyl and diaryl ethers by [3+3] cyclization of 3-alkoxy- and 3-aryloxy-1-siloxy-1,3-butadienes with 3-(silyloxy)alk-2-en-1-ones
  作者：Gerson Mroß、Peter Langer

  DOI：10.1016/j.tetlet.2006.09.126

  日期：2006.11

  Functionalized diaryl ethers were prepared by [3+3] cyclization of 3-aryloxy-1-siloxy-1,3-butadienes with 3-(silyloxy)alk-2-en-1-ones. (c) 2006 Elsevier Ltd. All rights reserved.