6-<(1,1-dimethylethyl)dimethylsilyloxy>-8-(trimethylsilyl)-1-octen-7-yne | 122700-27-0

• 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: 6-<(1,1-dimethylethyl)dimethylsilyloxy>-8-(trimethylsilyl)-1-octen-7-yne
• 英文别名: 3-(tert-butyldimethylsiloxy)-1-(trimethylsilyl)-oct-7-en-1-yne；tert-Butyl(dimethyl){[1-(trimethylsilyl)oct-7-en-1-yn-3-yl]oxy}silane；tert-butyl-dimethyl-(1-trimethylsilyloct-7-en-1-yn-3-yloxy)silane
• CAS: 122700-27-0
• 化学式: C₁₇H₃₄OSi₂
• 分子量: 310.627
• InChiKey: NZBSKROFBVEDRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  320.1±42.0 °C(Predicted)
• 密度：
  0.849±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  6-<(1,1-dimethylethyl)dimethylsilyloxy>-8-(trimethylsilyl)-1-octen-7-yne 在 potassium carbonate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 9.0h， 生成 (2RS,6RS)-2-(tert-butyldimethylsiloxy)bicyclo[4.3.0]non-1(9)-en-8-one
  参考文献：
  名称：

  New entry to the Pauson–Khand reaction: trimethylgermyl group at the triple bond terminus as a latent functional group

  摘要：

  The Pauson-Khand reaction of enynes possessing a trimethylgermyl group at the alkyne terminus afforded the corresponding bicyclo[3.3.0]octenone and bicyclo[4.3.0]nonenone skeletons in a stereoselective manner. The resulting trimethylgermyl group of the bicyclic compounds was then converted to the iodo group, which was used for further elaboration. Thus, the trimethylgermyl group at the triple bond terminus was shown to be a precursor for other appendages. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.041
• 作为产物：
  描述：

  5-己烯醛 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 6-<(1,1-dimethylethyl)dimethylsilyloxy>-8-(trimethylsilyl)-1-octen-7-yne
  参考文献：
  名称：

  New entry to the Pauson–Khand reaction: trimethylgermyl group at the triple bond terminus as a latent functional group

  摘要：

  The Pauson-Khand reaction of enynes possessing a trimethylgermyl group at the alkyne terminus afforded the corresponding bicyclo[3.3.0]octenone and bicyclo[4.3.0]nonenone skeletons in a stereoselective manner. The resulting trimethylgermyl group of the bicyclic compounds was then converted to the iodo group, which was used for further elaboration. Thus, the trimethylgermyl group at the triple bond terminus was shown to be a precursor for other appendages. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.041

文献信息

• Substrate control of diastereoselectivity in zirconium (II) mediated enyne cyclizations
  作者：Brian L. Pagenkopf、Eric C. Lund、Tom Livinghouse

  DOI：10.1016/0040-4020(94)01130-r

  日期：1995.4

  The reductive cyclization of an extensive series of chiral enynes by Cp2Zr(II) complexes has been examined. In most instances excellent substrate control of cyclization stereochemistry was observed.

  已经研究了Cp 2 Zr（II）配合物对一系列手性烯类化合物的还原环化作用。在大多数情况下，观察到出色的环化立体化学底物控制。
• A General Approach to Medium Ring Alkynes by Using Metathesis of Cobalt Hexacarbonyl Containing Dienes
  作者：David G. J. Young、Joseph A. Burlison、Ulf Peters

  DOI：10.1021/jo030011l

  日期：2003.5.1

  The assembly of medium sized rings (7-9) was achieved by using the metathesis of dienes linked by a cobalt hexacarbonyl complexed alkyne with either Grubbs' or Schrock's catalysts. The products of metathesis were subjected to transformations involving the dicobalt hexacarbonyl complexes, for example, decomplexation to liberate cyclic alkynes or Pauson-Khand reaction.
• Carbocyclisation of ω-ethylenic propargylic zinc reagents
  作者：Gilles Courtemanche、Jean-F. Normant

  DOI：10.1016/s0040-4039(00)92374-8

  日期：1991.9

  Omega-ethylenic propargylic zinc reagents undergo cyclisation. Particularly efficient are the reagents derived from propargylic ethers.
• On the origin of diastereoselection in the cyclization of enynes on low-valent zirconium centers. Substituent and torsional effects on annulation stereochemistry
  作者：Eric C. Lund、Tom Livinghouse

  DOI：10.1021/jo00280a005

  日期：1989.9
• New entry to the Pauson–Khand reaction: trimethylgermyl group at the triple bond terminus as a latent functional group
  作者：Chisato Mukai、Takashi Kozaka、Yukihiro Suzuki、In Jong Kim

  DOI：10.1016/j.tet.2004.01.041

  日期：2004.3

  The Pauson-Khand reaction of enynes possessing a trimethylgermyl group at the alkyne terminus afforded the corresponding bicyclo[3.3.0]octenone and bicyclo[4.3.0]nonenone skeletons in a stereoselective manner. The resulting trimethylgermyl group of the bicyclic compounds was then converted to the iodo group, which was used for further elaboration. Thus, the trimethylgermyl group at the triple bond terminus was shown to be a precursor for other appendages. (C) 2004 Elsevier Ltd. All rights reserved.