(E,E)-2-methyl-1-[(tert-butyldimethylsilyl)oxy]-1,3-pentadiene | 196710-91-5

• 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: (E,E)-2-methyl-1-[(tert-butyldimethylsilyl)oxy]-1,3-pentadiene
• 英文别名: (E,E)-2-methyl-1-[(tert-butyl)dimethylsilyl]-oxy-penta-1,3-diene；(E)-1-(1,1-dimethylethyl)dimethylsilyloxy-2-methyl-1,3-pentadiene；tert-butyl-dimethyl-[(1E,3E)-2-methylpenta-1,3-dienoxy]silane
• CAS: 196710-91-5
• 化学式: C₁₂H₂₄OSi
• 分子量: 212.407
• InChiKey: VRHCYWJGWAKZRV-BNFZFUHLSA-N

物化性质

• 沸点：
  212.8±8.0 °C(Predicted)
• 密度：
  0.830±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E,E)-2-methyl-1-[(tert-butyldimethylsilyl)oxy]-1,3-pentadiene 在 叔丁基二甲硅基三氟甲磺酸酯 、 二氧化硫 、 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Tandem Oxyallylations and Retro-ene Eliminations. One Pot Stereoselective Synthesis of Polypropionate Fragments with Three Contiguous Stereogenic Centers and One (E)-Alkene Unit.

  摘要：

  Mixtures of (EE)-2-methyl-1-silyloxypenta-1,3-dienes, enoxysilanes, SO2 and (t-Bu)Me2SiOTf (catalyst) generate (Z)-5-alkyl-1,3-dimethyl-6-oxo-4-silyloxyalk-2-enesulfinic acids that undergo stereoselective retro-ene eliminations of SO2 with the formation of corresponding (E)-3-hydroxy-2-alkyl-4-methylalk-5-en-1-ones with 2,3-syn and 3,4-anti diastereoselectivity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01398-1
• 作为产物：
  描述：

  2-methyl-pent-3t-enal 、 叔丁基二甲硅基三氟甲磺酸酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (E,E)-2-methyl-1-[(tert-butyldimethylsilyl)oxy]-1,3-pentadiene
  参考文献：
  名称：

  Use of 4-Cyanocoumarins as Dienophiles in a Facile Synthesis of Highly Substituted Dibenzopyranones

  摘要：

  A new synthesis of dibenzopyranones 14 is reported via the Diels-Alder cycloaddition of 4-cyanocoumarins 12 with 1-silyloxydienes 10 to give the adducts 13 which are then converted into 14 in one step via treatment with base and loss of the cyano and silyloxy groups.

  DOI：

  10.1021/ol802792g

文献信息

• Sulfur Dioxide-Mediated Syntheses of Polyfunctional Alkenes and (<i>E</i>,<i>Z</i>)- and (<i>E</i>,<i>E</i>)-2,4-Dien-1-ones
  作者：Laure C. Bouchez、Cotinica Craita、Pierre Vogel

  DOI：10.1021/ol050006z

  日期：2005.3.1

  Efficient methods for the stereoselective synthesis of polyfunctional (E)- and (Z)-alkenes and conjugated (E,E)- and (E,Z)-dienones are presented. They rely upon one-pot, four-component processes that condense 1-oxy-1,3-dienes, silyl enol ethers, SO2, and carbon electrophiles. [structure: see text]

  提出了多官能（E）-和（Z）-链烯以及共轭（E，E）-和（E，Z）-二烯酮的立体选择性合成的有效方法。他们依靠一锅四组分的方法来缩合1-氧-1,3-二烯，甲硅烷基烯醇醚，SO2和碳亲电试剂。[结构：见文字]
• Sulfur dioxide mediated one-pot, four-component synthesis of polyfunctional sulfones and sulfonamides, including medium-ring cyclic derivatives
  作者：Laure C. Bouchez、Māris Turks、Srinivas Reddy Dubbaka、Freddy Fonquerne、Cotinica Craita、Sylvain Laclef、Pierre Vogel

  DOI：10.1016/j.tet.2005.08.067

  日期：2005.11

  In previous papers (Synthesis 2002, 232 and J. Org. Chem. 2004, 69, 6413), we have shown that the hetero-Diels-Alder addition of sulfur dioxide to 1-oxy or 1,3-dioxy- 1,3-dienes generates zwitterions that add to enoxysilanes or allylsilanes giving silyl sulfinates that can be converted in the same pot into polyfunctional sulfones, sulfonamides or sulfonic esters. We are presenting further applications of this method, including the synthesis of new medium-size heterocyclic systems of the type tetrahydro-2H-thiocines and hexahydro-1,2-thiazonine. (c) 2005 Elsevier Ltd, All rights reserved.
• Use of 4-Cyanocoumarins as Dienophiles in a Facile Synthesis of Highly Substituted Dibenzopyranones
  作者：Michael E. Jung、Damian A. Allen

  DOI：10.1021/ol802792g

  日期：2009.2.5

  A new synthesis of dibenzopyranones 14 is reported via the Diels-Alder cycloaddition of 4-cyanocoumarins 12 with 1-silyloxydienes 10 to give the adducts 13 which are then converted into 14 in one step via treatment with base and loss of the cyano and silyloxy groups.
• Tandem Oxyallylations and Retro-ene Eliminations. One Pot Stereoselective Synthesis of Polypropionate Fragments with Three Contiguous Stereogenic Centers and One (E)-Alkene Unit.
  作者：Jean-Michel Roulet、Geneviève Puhr、Pierre Vogel

  DOI：10.1016/s0040-4039(97)01398-1

  日期：1997.9

  Mixtures of (EE)-2-methyl-1-silyloxypenta-1,3-dienes, enoxysilanes, SO2 and (t-Bu)Me2SiOTf (catalyst) generate (Z)-5-alkyl-1,3-dimethyl-6-oxo-4-silyloxyalk-2-enesulfinic acids that undergo stereoselective retro-ene eliminations of SO2 with the formation of corresponding (E)-3-hydroxy-2-alkyl-4-methylalk-5-en-1-ones with 2,3-syn and 3,4-anti diastereoselectivity. (C) 1997 Elsevier Science Ltd.