trimethyl[(3Z)-6-phenylhex-3-ene-1,5-diynyl]silane | 155187-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trimethyl[(3Z)-6-phenylhex-3-ene-1,5-diynyl]silane
• 英文别名: (Z)-6-phenyl-1-trimethylsilyl-3-hexen-1,5-diyne；1-phenyl-6-(trimethylsilyl)hexa-3-en-1,5-diyne；trimethyl-[(Z)-6-phenylhex-3-en-1,5-diynyl]silane
• CAS: 155187-28-3
• 化学式: C₁₅H₁₆Si
• 分子量: 224.378
• InChiKey: NCZIVHYNJYNZNO-PLNGDYQASA-N

物化性质

• 沸点：
  284.8±23.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  trimethyl[(3Z)-6-phenylhex-3-ene-1,5-diynyl]silane 在 copper(l) iodide 、 四(三苯基膦)钯 、 nBu₄NH₂ 、 potassium carbonate 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 106.0h， 生成 (3Z,7Z)-(1-chloroocta-3,7-diene-1,5-diynyl)benzene
  参考文献：
  名称：

  An Iterative Approach tocis-Oligodiacetylenes

  摘要：

  DOI：

  10.1002/1099-0690(200110)2001:20<3879::aid-ejoc3879>3.0.co;2-k
• 作为产物：
  描述：

  3-(tert-butyldimethylsilyl)-1-trimethylsilylprop-1-yne 在 potassium hydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 trimethyl[(3Z)-6-phenylhex-3-ene-1,5-diynyl]silane
  参考文献：
  名称：

  Stereoselective synthesis of enediynes and enynes by condensation of aldehydes with γ-(trialkylsilyl)allenylboranes

  摘要：

  Enediynes and enynes with high geometric purity were synthesized by treating acetylenic and simple aldehydes with gamma-(tert-butyldimethylsilyl)allenylborane 2a followed by the elimination step of the Peterson olefination reaction.

  DOI：

  10.1016/s0040-4039(00)61341-2

文献信息

• Synthesis of polyphenylene derivatives by thermolysis of enediynes and dialkynylaromatic monomers
  作者：Jens A John、James M Tour

  DOI：10.1016/s0040-4020(97)00977-0

  日期：1997.11

  Described are the syntheses of substituted enediynes and dialkynylaromatics using Pd- or cross coupling procedures. The products were then thermalized to afford the corresponding poly(p-phenylene)s, poly(1,4-naphthalene)s, poly(benzo[c]thiophene)s, and poly(dibenzothiophene)s. Fifteen examples are provided that show the scope of the polymerization process based upon substituent patterns and cyclization

  描述了使用Pd-或交叉偶联方法的取代烯二炔和二炔炔衍生物的合成。然后将产物加热，得到相应的聚（对苯撑），聚（1,4-萘），聚（苯并[ c]]噻吩和聚（二苯并噻吩）。提供了十五个实例，其基于取代基图案和环化部分显示了聚合过程的范围。使用热重分析法证明了新衍生的聚合物具有极好的热回弹性。通常使用与聚合物重复单元结构相似的小分子的红外数据相关性来确定聚合物的结构。由GCMS分析的二聚中间体的自由基捕获进一步证实了所提出的机理路线。通过监测单体消耗程度相对于聚合物分子量来确定逐步增长的聚合方式。
• Phane Properties of [2.2]Paracyclophane/Dehydrobenzoannulene Hybrids
  作者：Heino Hinrichs、Andrew J. Boydston、Peter G. Jones、Kirsten Hess、Rainer Herges、Michael M. Haley、Henning Hopf

  DOI：10.1002/chem.200600498

  日期：2006.9.18

  A series of [2.2]paracyclophane/dehydrobenzo[14]annulene (PC/DBA) hybrids (hydrocarbons 5, 6, 9, 10 b, and 10 c), [2.2]paracyclophane/dehydro[14]annulene (PC/DA) hybrids (7 and 8) and suitable model systems (11, 12, and 33) has been synthesized. Comparison of the electronic absorption spectra in each series of compounds provides further insight into the global communication between the decks in the

  一系列[2.2]对环烷/脱氢苯并[14]环戊烯（PC / DBA）杂化物（碳氢化合物5、6、9、10 b和10 c），[2.2]对环烷/脱氢[14]环戊烯（PC / DA）混合（7和8）和合适的模型系统（11、12和33）已经合成。比较每个系列化合物中的电子吸收光谱，可以进一步了解[2.2]对环环烷单元中各甲板之间的全局连通性。
• Synthesis of Polyphenylenes and Polynaphthalenes by Thermolysis of Enediynes and Dialkynylbenzenes
  作者：Jens A. John、James M. Tour

  DOI：10.1021/ja00090a066

  日期：1994.6

  Abstract : Described are the syntheses of substituted enediynes and dialkynylbenzenes using Pd- or Pd/Cu-catalyzed cross coupling procedures. The products were then thermalized, generally in benzene, to afford the corresponding poly(p-phenylene)s and poly(1,4-naphthalene)s. Thirteen examples are provided that show the scope of the polymerization process based upon substituent patterns and cyclization

  摘要：描述了使用 Pd 或 Pd/Cu 催化的交叉偶联程序合成取代的烯二炔和二炔基苯。然后将产物加热，通常在苯中，以提供相应的聚（对亚苯基）和聚（1,4-萘）。提供了 13 个示例，它们显示了基于取代基模式和环化部分的聚合过程的范围。使用热重分析证明了新衍生聚合物的极好的热弹性。聚合物结构通常使用红外数据与类似于聚合物重复单元结构的小分子的相关性来确认。通过 GCMS 分析的二聚中间体的自由基捕获进一步证实了所提出的机械路线。
• Novel and general cross-coupling reactions of alkynylzinc reagents and organotellurium compounds
  作者：Miguel J. Dabdoub、Vânia B. Dabdoub、Joseph P. Marino

  DOI：10.1016/s0040-4039(99)02088-2

  日期：2000.1

  The efficient cross-coupling reactions of different alkynyl organozinc reagents with unsaturated organotellurium species catalyzed by Pd(PPh3)4/CuI and using THF/DMF systems are described. These cross-coupling reactions are general and permit the formation of new sp–sp 2 carbon–carbon bonds. New reactions to reach the necessary alkynylzinc intermediates were also developed from terminal alkynes or

  描述了不同的炔基有机锌试剂与Pd（PPh 3）4 / CuI并使用THF / DMF系统催化的不饱和有机碲物种的有效交叉偶联反应。这些交叉偶联反应很普遍，并允许形成新的sp–sp 2碳–碳键。还从末端炔烃或使用炔属碲化物作为起始原料开发了新的反应，以达到必要的炔基锌中间体。
• Stereoselective Hydrogenolysis of 1,1-Dibromo-1-alkenes and Stereospecific Synthesis of Conjugated (<i>Z</i>)-Alkenyl Compounds
  作者：Jun'ichi Uenishi、Reiko Kawahama、Osamu Yonemitsu、Jiro Tsuji

  DOI：10.1021/jo9812781

  日期：1998.11.1

  The Pd-catalyzed hydrogenolysis of 1,1-dibromoalkenes with Bu3SnH occurs at room temperature stereoselectively to give (Z)-1-bromo-1-alkenes. We sought to determine the optimal reaction conditions and illustrate the scope of this method with 32 dibromoalkenes including alkenyl- and alkynyl-conjugated 1,l-dibromo-l-alkenes 7a-h and 2,2-disubstituted I,1-dibromo-1-alkenes 9a-f. Triphenylphosphine was the best ligand for the Pd-catalyzed hydrogenolysis. A wide range of solvents can be used for this reaction excluding EtOH, AcOH, and CHCl3. However, the reaction proceeds even in these solvents with the addition of a cosolvent or radical scavenger. The reaction of 1,1-diiodo-1-alkene (3) gave a mixture of (Z)-1-iodo-1-alkene (4), (Z)-1-tributylstannyl-1-alkene (5), and a terminal alkene 6, while that of 1,1-dichloroalkene did not occur. This selectivity can be explained by the stereoselective insertion of Pd(0) to a trans bromine-alkenyl carbon bond, successive transmetalation with Bu3SnH, and reductive elimination. The Suzuki and Sonogashira couplings of the resulting (Z)-1-bromo-1-alkenes with alkenyl(dialkoxy)borane and terminal alkyne occurred to give conjugated polyenes and enynes stereospecifically. The Pd-catalyzed hydrogenolysis of 1,l-dibromo-l-alkene and successive cross-coupling can be carried out either in a stepwise manner or in one-pot under the same Pd catalysis. These two processes should be useful for the synthesis of geometrically pure polyene and enyne with a Z-alkenyl unit.