(E)-3-tert-butyldiphenylsilyl-4-chloro-5-tetrahydropyranyloxy-pent-3-en-1-yne | 1191093-23-8

• 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: (E)-3-tert-butyldiphenylsilyl-4-chloro-5-tetrahydropyranyloxy-pent-3-en-1-yne
• 英文别名: tert-butyl-[(E)-4-chloro-5-(oxan-2-yloxy)pent-3-en-1-yn-3-yl]-diphenylsilane
• CAS: 1191093-23-8
• 化学式: C₂₆H₃₁ClO₂Si
• 分子量: 439.069
• InChiKey: SIOAMHOIAVGFTL-WCWDXBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-tert-butyldiphenylsilyl-4-chloro-5-tetrahydropyranyloxy-pent-3-en-1-yne 在 三乙烯二胺 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 溴乙酸乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 以93%的产率得到(2E,8E)-3,8-di(tert-butyldiphenylsilyl)-2,9-dichloro-1,10-bis-(tetrahydropyranyloxy)-deca-2,8-diene-4,6-diyne
  参考文献：
  名称：

  Synthesis of Hybrid Masked Triyne−Phenylene Axial Rods Containing (E)-β-Chlorovinylsilanes in the π-Conjugated Framework

  摘要：

  A two-directional synthesis of a masked hexayne 7, in which two beta-chlorovinylsilanes protect two of the internal alkynes, is reported. The key step involves the Pd-catalyzed oxidative dimerization of alkyne 10 to provide diyne 12, which is elaborated into centrosymmetric masked hexayne 7 in four steps. Masked hexayne 7 is a constitutional isomer of masked hexayne 2, which has been used as a monomer unit for oligoyne assembly. Although masked hexayne 7 was not as convenient a building block as 2 for application in oligoyne assembly, one of its precursors, namely alkyne 10, could be used successfully in Sonogashira couplings, which allowed the incorporation of aromatic spacers and the formation of hybrid masked triyne-phenylenes 20 and 28. Compounds 20 and 28 both contain removable end-groups, which will permit their application as building blocks for the assembly of classes of long-chain, pi-conjugated rod-like molecules. Rod-like molecule 34, which possesses a similar conjugated scaffold as 28, was also prepared by using a similar Strategy. Treatment of 34 with TBAF effected a 2-fold dechlorosilylation to provide a rigid rod molecule 35 in which two phenylene units interrupt an octayne scaffold.

  DOI：

  10.1021/jo901766p
• 作为产物：
  描述：

  (E)-3-tert-butyldiphenylsilyl-4-chloro-5-tetrahydropyranyloxy-1-trimethylsilylpent-3-en-1-yne 在 甲醇 、 potassium carbonate 作用下， 反应 3.0h， 以99%的产率得到(E)-3-tert-butyldiphenylsilyl-4-chloro-5-tetrahydropyranyloxy-pent-3-en-1-yne
  参考文献：
  名称：

  Synthesis of Hybrid Masked Triyne−Phenylene Axial Rods Containing (E)-β-Chlorovinylsilanes in the π-Conjugated Framework

  摘要：

  A two-directional synthesis of a masked hexayne 7, in which two beta-chlorovinylsilanes protect two of the internal alkynes, is reported. The key step involves the Pd-catalyzed oxidative dimerization of alkyne 10 to provide diyne 12, which is elaborated into centrosymmetric masked hexayne 7 in four steps. Masked hexayne 7 is a constitutional isomer of masked hexayne 2, which has been used as a monomer unit for oligoyne assembly. Although masked hexayne 7 was not as convenient a building block as 2 for application in oligoyne assembly, one of its precursors, namely alkyne 10, could be used successfully in Sonogashira couplings, which allowed the incorporation of aromatic spacers and the formation of hybrid masked triyne-phenylenes 20 and 28. Compounds 20 and 28 both contain removable end-groups, which will permit their application as building blocks for the assembly of classes of long-chain, pi-conjugated rod-like molecules. Rod-like molecule 34, which possesses a similar conjugated scaffold as 28, was also prepared by using a similar Strategy. Treatment of 34 with TBAF effected a 2-fold dechlorosilylation to provide a rigid rod molecule 35 in which two phenylene units interrupt an octayne scaffold.

  DOI：

  10.1021/jo901766p

文献信息

• Synthesis of Hybrid Masked Triyne−Phenylene Axial Rods Containing (<i>E</i>)-β-Chlorovinylsilanes in the π-Conjugated Framework
  作者：Michael D. Weller、Benson M. Kariuki、Liam R. Cox

  DOI：10.1021/jo901766p

  日期：2009.10.16

  A two-directional synthesis of a masked hexayne 7, in which two beta-chlorovinylsilanes protect two of the internal alkynes, is reported. The key step involves the Pd-catalyzed oxidative dimerization of alkyne 10 to provide diyne 12, which is elaborated into centrosymmetric masked hexayne 7 in four steps. Masked hexayne 7 is a constitutional isomer of masked hexayne 2, which has been used as a monomer unit for oligoyne assembly. Although masked hexayne 7 was not as convenient a building block as 2 for application in oligoyne assembly, one of its precursors, namely alkyne 10, could be used successfully in Sonogashira couplings, which allowed the incorporation of aromatic spacers and the formation of hybrid masked triyne-phenylenes 20 and 28. Compounds 20 and 28 both contain removable end-groups, which will permit their application as building blocks for the assembly of classes of long-chain, pi-conjugated rod-like molecules. Rod-like molecule 34, which possesses a similar conjugated scaffold as 28, was also prepared by using a similar Strategy. Treatment of 34 with TBAF effected a 2-fold dechlorosilylation to provide a rigid rod molecule 35 in which two phenylene units interrupt an octayne scaffold.