(E)-2-chloro-3-triethylsilyl-5-tri(propan-2-yl)silylpent-2-en-4-ynal | 619308-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-chloro-3-triethylsilyl-5-tri(propan-2-yl)silylpent-2-en-4-ynal
• CAS: 619308-95-1
• 化学式: C₂₀H₃₇ClOSi₂
• 分子量: 385.137
• InChiKey: CFZGNEQRGUNXDU-FMQUCBEESA-N

物化性质

• 沸点：
  394.9±42.0 °C(predicted)
• 密度：
  0.924±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-chloro-3-triethylsilyl-5-tri(propan-2-yl)silylpent-2-en-4-ynal 在 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 (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：

  5-triethylsilanyloxy-1-triisopropylsilanyl-penta-1,3-diyne 在 (trimethylstannyl)lithium 、 manganese(IV) oxide 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (E)-2-chloro-3-triethylsilyl-5-tri(propan-2-yl)silylpent-2-en-4-ynal
  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.