(E)-tert-butyldimethylsilyl-(4,4-ethylenedioxy-3-methylbut-2-en-1-yl) ether | 163395-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: (E)-tert-butyldimethylsilyl-(4,4-ethylenedioxy-3-methylbut-2-en-1-yl) ether
• 英文别名: tert-butyl-[(E)-3-(1,3-dioxolan-2-yl)but-2-enoxy]-dimethylsilane
• CAS: 163395-64-0
• 化学式: C₁₃H₂₆O₃Si
• 分子量: 258.433
• InChiKey: SSDWUZWGWWNISY-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (E)-tert-butyldimethylsilyl-(4,4-ethylenedioxy-3-methylbut-2-en-1-yl) ether 在 正丁基锂 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 生成 8-(tert-butyldimethylsilanyloxy)-2,6-dimethylocta-2,4,6-trienoic acid methyl ester
  参考文献：
  名称：

  Didehydrofarnesyl diphosphate: an intrinsically fluorescent inhibitor of protein farnesyltransferase

  摘要：

  Didehydrofarnesyl diphosphate (DeltaDeltaFPP), a fluorescent pentaene analogue of farnesyl diphosphate (FPP), was synthesized using stereoselective Wittig reactions. Although DeltaDeltaFPP was not an alternative substrate for yeast protein farnesyltransferase (FTase), the fluorescent analogue was a potent competitive inhibitor with a K-i value of 8.8 muM (K-m (FPP) = 27 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.077
• 作为产物：
  描述：

  3-甲酰基-2-丁烯酸乙酯 在 咪唑 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 6.25h， 生成 (E)-tert-butyldimethylsilyl-(4,4-ethylenedioxy-3-methylbut-2-en-1-yl) ether
  参考文献：
  名称：

  The suzuki reaction in stereocontrolled polyene synthesis: Retinol (vitamin A), its 9- and/or 13-demethyl analogs, and related 9-demethyl-dihydroretinoids

  摘要：

  A new synthesis of retinol (vitamin A) and 9- and/or 13-demethylretinols, with essentially complete control of regio- and stereochemistry, is described which is based on the thallium-accelerated, palladium-catalyzed cross-coupling reactions of (E)-1-alkenylboronic acids and (E)-1-alkenyl iodides (Suzuki reaction). The procedure has also been extended to the stereocontrolled synthesis of a series of 9-demethyl-dihydroretinoids of potential biological interest.

  DOI：

  10.1016/0040-4020(94)01108-c

文献信息

• The suzuki reaction in stereocontrolled polyene synthesis: Retinol (vitamin A), its 9- and/or 13-demethyl analogs, and related 9-demethyl-dihydroretinoids
  作者：Alicia Torrado、Beatriz Iglesias、Susana López、Angel R. de Lera

  DOI：10.1016/0040-4020(94)01108-c

  日期：1995.2

  A new synthesis of retinol (vitamin A) and 9- and/or 13-demethylretinols, with essentially complete control of regio- and stereochemistry, is described which is based on the thallium-accelerated, palladium-catalyzed cross-coupling reactions of (E)-1-alkenylboronic acids and (E)-1-alkenyl iodides (Suzuki reaction). The procedure has also been extended to the stereocontrolled synthesis of a series of 9-demethyl-dihydroretinoids of potential biological interest.
• Stereospecific synthesis of 9-demethylretinoids via palladium-catalyzed vinylboronic acid-vinyl iodide cross coupling
  作者：Angel R. de Lera、Alicia Torrado、Beatriz Iglesias、Susana López

  DOI：10.1016/s0040-4039(00)60044-8

  日期：1992.10

  A stereospecific synthesis of 9-demethylretinoids with either trans or 11-cis geometries, based on the thallium-accelerated palladium-catalyzed cross-coupling reactions of an (E)-1-alkenylboronic acid and (E) or (Z)-alkenyl iodides, is described.
• Didehydrofarnesyl diphosphate: an intrinsically fluorescent inhibitor of protein farnesyltransferase
  作者：Xiao-hui Liu、Glenn D. Prestwich

  DOI：10.1016/j.bmcl.2004.02.077

  日期：2004.5

  Didehydrofarnesyl diphosphate (DeltaDeltaFPP), a fluorescent pentaene analogue of farnesyl diphosphate (FPP), was synthesized using stereoselective Wittig reactions. Although DeltaDeltaFPP was not an alternative substrate for yeast protein farnesyltransferase (FTase), the fluorescent analogue was a potent competitive inhibitor with a K-i value of 8.8 muM (K-m (FPP) = 27 muM). (C) 2004 Elsevier Ltd. All rights reserved.