(1E,3E,5E)-1,6-bis(trimethylsilyl)hexa-1,3,5-triene | 133683-82-6

• 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: (1E,3E,5E)-1,6-bis(trimethylsilyl)hexa-1,3,5-triene
• 英文别名: trimethyl-[(1E,3E,5E)-6-trimethylsilylhexa-1,3,5-trienyl]silane
• CAS: 133683-82-6
• 化学式: C₁₂H₂₄Si₂
• 分子量: 224.494
• InChiKey: GOMIPTCDZFZSPL-BGSVYHRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (1E,3E,5E)-1,6-bis(trimethylsilyl)hexa-1,3,5-triene 在 sodium tetrahydroborate 、 三氯化铝 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 methyl 5ζ,12ζ-dihydroxy-6(E),8(E),10(E)-eicosatrienoate
  参考文献：
  名称：

  Conjugated polyene synthesis via disilyl derivatives: a direct access to ostopanic acid, a plant anticancer agent, and to (6E)-LTB3 leukotriene

  摘要：

  DOI：

  10.1021/jo00021a056

文献信息

• Highly Stereoselective Synthesis of Conjugated Polyenes via a Homocoupling Reaction of Unsaturated Silanes
  作者：Francesco Babudri、Angela R. Cicciomessere、Gianluca M. Farinola、Vito Fiandanese、Giuseppe Marchese、Roberta Musio、Francesco Naso、Oronzo Sciacovelli

  DOI：10.1021/jo9700437

  日期：1997.5.1

  A new method for the synthesis of conjugated polyenes containing up to eight double bonds with all-E configuration is reported. The procedure is based upon a homocoupling reaction of dienyl-, trienyl-, or tetraenylsilanes, promoted by PdCl(2) in methanol and in the presence of LiCl and CuCl(2). Configurational and conformational assignments were rigorously made on the basis of NMR spectra. The compounds

  报道了一种新的合成共轭多烯的新方法，该共轭多烯含有多达8个全E构型的双键。该程序基于PdCl（2）在甲醇中以及在LiCl和CuCl（2）的存在下，二烯基，三烯基或四烯基硅烷的均偶联反应。在NMR光谱的基础上严格进行构型和构象分配。获得的化合物代表了一类新颖的有趣的对称取代的多烯，具有潜在的光学和电光学特性。通过改变溶剂，可以将均偶联过程切换为甲硅烷基取代的末端双键的卤化反应，从而导致聚烯基卤化物。
• A new approach to silylated ketones and dicarbonyl compounds with a conjugated (all E) diene or triene structure
  作者：Francesco Babudri、Vito Fiandanese、Giuseppe Marchese、Francesco Naso

  DOI：10.1039/c39910000237

  日期：——

  Silylated ketones and dicarbonyl compounds with a conjugated diene or triene structure are obtained by electrophilic substitution reactions between (1E, 3E)-1,4-bis(trimethylsilyl)buta-1,3-diene or (1E, 3E, 5E)-1,6-bis(trimethylsilyl)hexa-1,3,5-triene and acyl chlorides in the presence of aluminium trichloride.

  通过（1 E，3 E）-1,4-双（三甲基甲硅烷基）丁1,3-二烯或（1 E，3 E，在三氯化铝存在下的5 E）-1,6-双（三甲基甲硅烷基）己-1,3,5-三烯和酰氯。
• A straightforward route to polyenylsilanes by palladium- or nickel-catalyzed cross-coupling reactions
  作者：Francesco Babudri、Gianluca M. Farinola、Vito Fiandanese、Luigia Mazzone、Francesco Naso

  DOI：10.1016/s0040-4020(97)10209-5

  日期：1998.2

  ipso-borodesilylation with BCl3 followed by Pd-catalyzed coupling reactions of the resulting boron derivative with aryl halides, whereas the synthesis of alkyl substituted polyenes requires the conversion of the boron intermediate into iodo-derivative and the subsequent coupling with alkyl Grignard reagents in the presence of a Ni(II) catalyst.

  描述了通过交叉偶联反应将双甲硅烷基化的二烯和三烯有效转化为多烯基硅烷。的芳基取代的多烯是由合成本位-borodesilylation与Bcl 3，随后加入Pd催化的偶联与芳基卤将所得硼衍生物的反应，而烷基取代的多烯的合成需要硼中间体转化成碘-衍生物和随后的在Ni（II）催化剂存在下与烷基Grignard试剂偶联。
• A Direct Access to a Potential LTB₄-Antagonist, SM-9064,<i>via</i>, Disilyl Derivatives
  作者：Vito Fiandanese、Angela Punzi

  DOI：10.1080/00397919308009765

  日期：1993.1

  Abstract The synthesis of SM-9064, a potential LTB4 antagonist, which is effective in some types of inflammation, has been easily achieved in a few steps by electrophilic substitution reactions between (1E,3E,5E)-1,6-bis(trimethylsilyl)-1,3,5-hexatriene and acyl chlorides in the presence of aluminum trichloride, followed by reduction reaction and formation of pyrrolidine derivative.

  摘要 SM-9064 是一种潜在的 LTB4 拮抗剂，对某些类型的炎症有效，通过 (1E,3E,5E)-1,6-双(三甲基甲硅烷基)-1,3,5-己三烯和酰氯在三氯化铝存在下进行还原反应并形成吡咯烷衍生物。
• An easy stereoselective approach to polyunsaturated silylated sulfides
  作者：Vito Fiandanese、Luigia Mazzone

  DOI：10.1016/s0040-4039(00)60935-8

  日期：1992.11

  Stereodefined monosilylated dienyl and trienylsulfides have been easily prepared by means of chemoselective substitution reactions on unsaturated disilyl derivatives.