3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-3,6-dimethyl-octa-1,7-diyne | 188345-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-3,6-dimethyl-octa-1,7-diyne
• 英文别名: tert-butyl-[6-[tert-butyl(dimethyl)silyl]oxy-3,6-dimethylocta-1,7-diyn-3-yl]oxy-dimethylsilane
• CAS: 188345-88-2
• 化学式: C₂₂H₄₂O₂Si₂
• 分子量: 394.745
• InChiKey: BIINGEBNVVMSIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-3,6-dimethyl-octa-1,7-diyne 在 N,N-二甲基丙烯基脲 、 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,4S)-1,4-Dimethyl-cyclotrideca-5,12-diyne-1,4-diol
  参考文献：
  名称：

  meso-1,11-Dimethylcyclotrideca-2,9-diyne-1,11-diol

  摘要：

  The title compound, C15H22O2, (5), has been prepared and its structure determined. At room temperature, two conformations are observed, but at 193 K, the compound shows only the conformation which has 67% occupancy at room temperature. The appearance of two conformations and the low symmetry of compound (5) are in accordance with the general structural behaviour of 13-membered-ring systems. meso-(5) crystallizes in the monoclinic space group I2/a. The lengths of the triple bonds are close to 1.175 Angstrom at room temperature and 1.188 Angstrom at 193 K. The bond angles at the triple bonds deviate by less than 7 degrees from being linear and are almost temperature independent.

  DOI：

  10.1107/s0108270196013789
• 作为产物：
  描述：

  2,5-己二酮 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-3,6-dimethyl-octa-1,7-diyne
  参考文献：
  名称：

  Racemic 3,6-Dimethyl-3,6-bis(tert-butyldimethylsilyloxy)-1,7-cyclododecadiyne

  摘要：

  The title compound, C26H48O2Si2, has been prepared and its structure determined. The bond angles at the triple bond are close to 174.5 degrees (average) and the length of the triple bond is 1.179(3)Angstrom. The alkylene chains maintain a screw-type arrangement similar to that found in unsubstituted cyclododecane.

  DOI：

  10.1107/s0108270196004891

文献信息

• Synthesis and Structure of Functionalized Cyclododecadiynes and -dienes
  作者：Christoph Boss、Reinhart Keese

  DOI：10.1002/hlca.19960790811

  日期：1996.12.11

  The cyclododecadiynes 3b–d, 8b–d, and 10b–c with functionalities in two propargylic positions, as well as the monofunctionalized diyne 13b have been prepared from simple open-chain building blocks. In the DMPU ( = N,N'-dimethylpropyleneurea)-assisted ring-closing alkylation of 1,7-diynes, the twelve-membered ring compounds have been prepared in yields of 16–55%. The preparation of the diene-diyne 15

  环十二碳二炔3b-d，8b-d和10b-c在两个炔丙基位置具有功能性，以及单官能化的二炔13b已由简单的开链结构单元制备。在DMPU（= N，N'-二甲基丙烯脲）辅助的1,7-二炔的闭环烷基化反应中，制备了十二元环化合物，产率为16-55％。描述了二烯-二炔15和环十二烷基-5,11-二炔-1,4-二酮18的制备。
• The First Crystal Structure Analysis of Cyclododeca-2,8-diyne-1,10-diols
  作者：C. Boss、H. Stoeckli-Evans、R. Keese

  DOI：10.1107/s0108270196009080

  日期：1996.12.15

  Cyclododeca-2,8-diyne-1,10-diol, (6), C12H16O2, and 1,10-dimethylcyclododeca-2,8-diyne-1,10-diol, (11), C14H20O2, have been prepared and their structures determined. Both crystallize in centrosymmetric space groups and the molecules have approximate C-2 symmetry. For compound (6), the lengths of the triple bonds are 1.184(3) (C2=C3) and 1.189(3) Angstrom (C8=C9). The bond angles at the triple bonds (C1-C2=C3 and C8=C9-C-10) deviate by less than 6 degrees from 180 degrees. For compound (11), the lengths of the triple bonds are 1.190(3) (C2=C3) and 1.188(3) Angstrom (C8=C9), and the bond angles at the triple bonds are close to 175.5 degrees. In both compounds, the two 3-hexyne chains maintain a 'crossed' arrangement whereas the two alkylene chains are arranged in a manner similar to that described for unsubstituted cyclododecane.
• <i>meso</i>-3,6-Dimethyl-3,6-bis(<i>tert</i>-butyldimethylsilyloxy)-1,7-octadiyne
  作者：A. Wicki、S. Grüschow、T. Lüthi、J. von Grothe、S. Capelli、J. Hauser、R. Keese

  DOI：10.1107/s0108270197016855

  日期：1998.3.15

  The title compound, C22H42O2Si2, shows a strictly antiperiplanar arrangement of the alkane chain with dihedraI angles between the terminal alkyne groups and the alkane chains of -55 (6) and -60.7 (4)degrees. The central C-C bond contains the centre of inversion, The crystal packing shows interwoven meanders of the antiperiplanar 3,6-disubstituted diynes, with the methyl groups filling the space in between. The tert-butyldimethylsilyloxy groups of two meandering chains are oriented towards each other, The absolute values of the crystal data are compared with the data for rac-3,6-dimethyl-3,6-bis(tert-butyldimethylsilyloxy)1,7- cyclododecadiyne [Boss et al. (1996). Acta Cryst, C52, 2370-2372].
• Synthesis of cycloalkadiynes of various ring size
  作者：Christoph Boss、Reinhart Keese

  DOI：10.1016/s0040-4020(97)00067-7

  日期：1997.3

  The synthesis of the 10-, 11-, 13-, 14- and 16-membered cycloalkadiynes 3a-b, 4a-b, 6a-b, 7a-b, 10a-b and 11a-b containing functional groups either in two propargylic or two homopropargylic positions is described. The key step of the synthetic scheme is the DMPU assisted double alkylation of two terminal alkyne units leading to the carbocycles mentioned above in moderate to good yield via a three step pathway. (C) 1997 Elsevier Science Ltd.