5-(tert-butyldiphenylsilyloxy)-1-(trimethylsilyl)penta-1,3-diyne | 619308-84-8

• 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: 5-(tert-butyldiphenylsilyloxy)-1-(trimethylsilyl)penta-1,3-diyne
• 英文别名: Tert-butyl-diphenyl-(5-trimethylsilylpenta-2,4-diynoxy)silane；tert-butyl-diphenyl-(5-trimethylsilylpenta-2,4-diynoxy)silane
• CAS: 619308-84-8
• 化学式: C₂₄H₃₀OSi₂
• 分子量: 390.673
• InChiKey: FZVPTJYLVSCFNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  5-(tert-butyldiphenylsilyloxy)-1-(trimethylsilyl)penta-1,3-diyne 在 (trimethylstannyl)lithium 、 manganese(IV) oxide 、 copper(I) bromide dimethylsulfide complex 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (E)-3-(tert-butyldiphenylsilyl)-4-chloro-6,6-dibromo-1-(trimethylsilyl)-hexa-3,5-dien-1-yne
  参考文献：
  名称：

  Stereoselective Synthesis of β-(Chloro)vinylsilanes Using a Regio- and (E)-Stereoselective Bis-Stannylation of Unsymmetrically Substituted Butadiynes:  Application to the Synthesis of a Masked Triyne

  摘要：

  A highly regio- and stereoselective bis-stannylation of unsymmetrically substituted butadiyne 3 provides bis-stannane 4. Selective lithiation of the internal tin residue effects a 1,4-retro-Brook rearrangement to afford vinylsilane 5. This was elaborated into the novel diethynylethene 1, which also functions as a masked triyne.

  DOI：

  10.1021/ol035536e
• 作为产物：
  描述：

  5-(trimethylsilyl)penta-2,4-diyn-1-ol 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以99%的产率得到5-(tert-butyldiphenylsilyloxy)-1-(trimethylsilyl)penta-1,3-diyne
  参考文献：
  名称：

  β-Chlorovinylsilanes as masked alkynes in oligoyne assembly: synthesis of the first aryl-end-capped dodecayne

  摘要：

  利用氟化物介导的四倍脱氯硅烷化作用，制备了一种芳基末端封端的十二烷，该封端十二烷前体含有四个作为封端炔烃的δ-氯乙烯基硅烷残基；不稳定的十二烷产物通过紫外-可见吸收光谱和 "无基质 "MALDI-TOF质谱进行了表征。

  DOI：

  10.1039/b707681a

文献信息

• Stereoselective Synthesis of β-(Chloro)vinylsilanes Using a Regio- and (<i>E</i>)-Stereoselective Bis-Stannylation of Unsymmetrically Substituted Butadiynes:  Application to the Synthesis of a Masked Triyne
  作者：Simon M. E. Simpkins、Benson M. Kariuki、Caterina S. Aricó、Liam R. Cox

  DOI：10.1021/ol035536e

  日期：2003.10.1

  A highly regio- and stereoselective bis-stannylation of unsymmetrically substituted butadiyne 3 provides bis-stannane 4. Selective lithiation of the internal tin residue effects a 1,4-retro-Brook rearrangement to afford vinylsilane 5. This was elaborated into the novel diethynylethene 1, which also functions as a masked triyne.
• β-Chlorovinylsilanes as masked alkynes in oligoyne assembly: synthesis of the first aryl-end-capped dodecayne
  作者：Simon M. E. Simpkins、Michael D. Weller、Liam R. Cox

  DOI：10.1039/b707681a

  日期：——

  An aryl-end-capped dodecayne has been prepared using a four-fold fluoride-mediated dechlorosilylation of a masked dodecayne precursor containing four β-chlorovinylsilane residues that serve as masked alkynes; the unstable dodecayne product has been characterised by UV-vis absorption spectroscopy and ‘matrix-free’ MALDI-TOF mass spectrometry.

  利用氟化物介导的四倍脱氯硅烷化作用，制备了一种芳基末端封端的十二烷，该封端十二烷前体含有四个作为封端炔烃的δ-氯乙烯基硅烷残基；不稳定的十二烷产物通过紫外-可见吸收光谱和 "无基质 "MALDI-TOF质谱进行了表征。