(E)-4,4-ethylenedioxy-3-methylbut-2-en-1-ol | 65527-78-8

• 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)-4,4-ethylenedioxy-3-methylbut-2-en-1-ol
• 英文别名: (E)-3-(<1.3>Dioxolan-2-yl)-but-2-en-1-ol；(E)-3-(1,3-dioxolan-2-yl)but-2-en-1-ol
• CAS: 65527-78-8
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: MWEPUOMJGRJDTP-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4,4-ethylenedioxy-3-methylbut-2-en-1-ol 在 咪唑 、 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 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 乙醚 为溶剂， 生成 (E)-4,4-ethylenedioxy-3-methylbut-2-en-1-ol
  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

文献信息

• γ-Allenyl Allyl Benzothiazole Sulfonyl Anions Undergo<i>cis</i>-Selective (Sylvestre) Julia Olefinations
  作者：Angel R. de Lera、Belén Vaz、Rosana Alvarez、José A. Souto

  DOI：10.1055/s-2004-837214

  日期：——

  γ-Allenyl allyl benzothiazolyl sulfones 8 and ent-8 provided allenyl trienes and polyenes with cis-selectivities ranging from 71:29 to 100:0 upon condensation (NaHMDS, THF, -78 °C to 25 °C) with a variety of unsaturated aldehydes.

  γ-烯丙基苯并噻唑基砜 8 和 ent-8 提供了顺式选择性范围为 71:29 至 100:0 的丙二烯基三烯和多烯（NaHMDS、THF、-78 °C 至 25 °C）与各种不饱和醛类。
• 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.