[(3E)-6,6-dibromo-4-chloro-3-triethylsilylhexa-3,5-dien-1-ynyl]-tri(propan-2-yl)silane | 619308-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3E)-6,6-dibromo-4-chloro-3-triethylsilylhexa-3,5-dien-1-ynyl]-tri(propan-2-yl)silane
• CAS: 619308-99-5
• 化学式: C₂₁H₃₇Br₂ClSi₂
• 分子量: 540.957
• InChiKey: IRBBCYJEPVZVRX-FMQUCBEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.38
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  [(3E)-6,6-dibromo-4-chloro-3-triethylsilylhexa-3,5-dien-1-ynyl]-tri(propan-2-yl)silane 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以84%的产率得到(E)-4-Chloro-3-triethylsilanyl-1-triisopropylsilanyl-hex-3-ene-1,5-diyne
  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：

  (E)-2-Chloro-3-triethylsilanyl-5-triisopropylsilanyl-pent-2-en-4-yn-1-ol 在 manganese(IV) oxide 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 [(3E)-6,6-dibromo-4-chloro-3-triethylsilylhexa-3,5-dien-1-ynyl]-tri(propan-2-yl)silane
  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

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.