(2E)-5-(t-Butyl-dimethylsilyloxy)-2-hexen-1-ol | 79414-08-7

• 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: (2E)-5-(t-Butyl-dimethylsilyloxy)-2-hexen-1-ol
• 英文别名: (E)-5-(tert-butyldimethylsiloxy)-2-hexen-1-ol；2-Hexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (E)-(+/-)-；(E)-5-[tert-butyl(dimethyl)silyl]oxyhex-2-en-1-ol
• CAS: 79414-08-7
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: XVQJCIIATZRUJV-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-5-(t-Butyl-dimethylsilyloxy)-2-hexen-1-ol 在 四(三苯基膦)钯 吡啶 、 高氯酸 、 sodium hydride 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 39.25h， 生成 (E)-methyl 2-methyl-12-oxo-7-(phenylsulfonyl)oxacyclododec-4-ene-7-carboxylate
  参考文献：
  名称：

  Cyclization catalyzed by palladium(0). Initial studies and macrolide formation

  摘要：

  DOI：

  10.1021/ja00534a030
• 作为产物：
  描述：

  5-[tert-butyl(dimethyl)silyl]oxyhex-2-yn-1-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到(2E)-5-(t-Butyl-dimethylsilyloxy)-2-hexen-1-ol
  参考文献：
  名称：

  摘要：

  Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Cecidomyiidae). Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of pheromone extract, followed by renewed GC-EAD analysis, revealed a new EAD-active compound with chromatographic characteristics identical to those of tridecan-2-yl acetate on five fused silica columns (DB-5, DB-210, DB-23, SP-1000, and Cyclodex-B). Syntheses, chromatography, and retention index calculations of all possible tridecen-2-yl acetates suggested that the candidate pheromone A was a tridecadien-2-yl acetate with nonconjugated double bonds. Synthetic candidate pheromone component (Z,Z)-4,7-tridecadien-2-yl acetate (Z4Z7) cochromatographed with A on all analytical columns and elicited comparable antennal activity. In GC-EAD analyses that separated the enantiomers (Z,Z)4,7-tridecadien-(S)-2-yl acetate (2S-Z4Z7) and (Z,Z)-4,7-tridecadien-(R)-2-yl acetate (2R-Z4Z7) with baseline resolution, only 2S-Z4Z7 as a component in a racemic standard or in pheromone extract elicited antennal responses. In Douglas-fir seed orchards, sticky traps baited with 2S-Z4Z7 captured male C. oregonensis, whereas 2R-Z4Z7 was behaviorally benign. Comparable catches of males in traps baited with racemic Z4Z7 (50 mug) or virgin female C. oregonensis suggested that synthetic pheromone baits could be developed for monitoring C. oregonensis populations in commercial Douglas-fir seed orchards.

  DOI：

  10.1023/a:1021005517389

文献信息

• Convergent stereospecific total synthesis of monochiral Monocillin I related macrolides
  作者：Maxime Lampilas、Robert Lett

  DOI：10.1016/s0040-4039(00)77712-4

  日期：1992.2

  The first total synthesis of Monocillin I related macrolides has been achieved by a convergent and stereospecific route involving the palladium - catalyzed coupling of a functionnalized chiral vinylstannane with the appropriate dimethoxy bromomethyl isocoumarin. Cleavage conditions of the isocoumarin ring were then found for the preparation of a precursor hydroxy acid. The 14-membered macrolide was

  Monocillin I相关大环内酯类化合物的第一个全合成方法是通过聚合和立体定向途径实现，该途径涉及功能化手性乙烯基锡烷与适当的二甲氧基溴甲基异香豆素的钯催化偶联。然后发现异香豆素环的裂解条件以制备前体羟基酸。在Mitsunobu反应条件下获得14元大环内酯，并从该大环前体立体定向生成所需的Monocillin I天然共轭二烯酮环氧体系。
• Doppelt und dreifach funktionalisierte, enantiomerenreine C₄-Synthesebausteine aus β-Hydroxybuttersäure, Äpfelsäure und Weinsäure
  作者：Ernst Hungerbühler、Dieter Seebach、Daniel Wasmuth

  DOI：10.1002/hlca.19810640523

  日期：1981.7.22

  Enantiomerically Pure Synthetic Building Blocks with Four C-Atoms and Two or Three Functional Groups from β-Hydroxy-butanoic, Malic, and Tartaric Acid

  具有四个C原子和两个或三个来自β-羟基丁酸，苹果酸和酒石酸的官能团的对映体纯合成构件
• HUNGERBUEHLER E.; SEEBACH D.; WASMUTH D., HELV. CHIM. ACTA, 1981, 64, NO 5, 1467-1487
  作者：HUNGERBUEHLER E.、 SEEBACH D.、 WASMUTH D.

  DOI：——

  日期：——
• Cyclization catalyzed by palladium(0). Initial studies and macrolide formation
  作者：Barry M. Trost、Thomas R. Verhoeven

  DOI：10.1021/ja00534a030

  日期：1980.7
• ——
  作者：Regine Gries、Grigori Khaskin、Gerhard Gries、Robb G. Bennett、G. G. Skip King、Petra Morewood、Keith N. Slessor、W. Dean Morewood

  DOI：10.1023/a:1021005517389

  日期：——

  Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Cecidomyiidae). Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of pheromone extract, followed by renewed GC-EAD analysis, revealed a new EAD-active compound with chromatographic characteristics identical to those of tridecan-2-yl acetate on five fused silica columns (DB-5, DB-210, DB-23, SP-1000, and Cyclodex-B). Syntheses, chromatography, and retention index calculations of all possible tridecen-2-yl acetates suggested that the candidate pheromone A was a tridecadien-2-yl acetate with nonconjugated double bonds. Synthetic candidate pheromone component (Z,Z)-4,7-tridecadien-2-yl acetate (Z4Z7) cochromatographed with A on all analytical columns and elicited comparable antennal activity. In GC-EAD analyses that separated the enantiomers (Z,Z)4,7-tridecadien-(S)-2-yl acetate (2S-Z4Z7) and (Z,Z)-4,7-tridecadien-(R)-2-yl acetate (2R-Z4Z7) with baseline resolution, only 2S-Z4Z7 as a component in a racemic standard or in pheromone extract elicited antennal responses. In Douglas-fir seed orchards, sticky traps baited with 2S-Z4Z7 captured male C. oregonensis, whereas 2R-Z4Z7 was behaviorally benign. Comparable catches of males in traps baited with racemic Z4Z7 (50 mug) or virgin female C. oregonensis suggested that synthetic pheromone baits could be developed for monitoring C. oregonensis populations in commercial Douglas-fir seed orchards.