5-<(tert-butyl)dimethylsilyloxy>-5-(ethynyl)nona-1,8-diene | 177196-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-<(tert-butyl)dimethylsilyloxy>-5-(ethynyl)nona-1,8-diene
• 英文别名: 5-ethynyl-5-(tert-butyldimethylsilyloxy)-nona-1,8-diene；5-(tertbutyldimethylsilyloxy)-5-ethynyl-1,8-nonadiene；Tert-butyl-(5-ethynylnona-1,8-dien-5-yloxy)-dimethylsilane
• CAS: 177196-50-8
• 化学式: C₁₇H₃₀OSi
• 分子量: 278.51
• InChiKey: WLSPCBRBHUBGPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  5-<(tert-butyl)dimethylsilyloxy>-5-(ethynyl)nona-1,8-diene 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 135.0h， 生成 rac-(1R,4R,7S,10R)-7-(methylsulfonyloxy)tetracyclo-[5.4.1.0(4,12).0(10,12)]dodecan-2-one
  参考文献：
  名称：

  The quest for planarizing distortions in hydrocarbons: two stereoisomeric [4.5.5.5]fenestranes

  摘要：

  According to semiempirical calculations the planarizing distortions in the central C(C)4 substructure of fenestranes, represented as 1, can be enhanced by a variety of structural modifications. Based on these results we selected the 7-hydroxy-c,c,c,c- and c,t,c,c[4.5.5.5]fenestranones 13 and 16 as precursors for the introduction of a bridgehead double bond. The efficient synthesis of these precursors and their chemical transformations are reported. Attempts to activate the hydroxyl group in 16 for introduction of a bridgehead double bond led to the rearrangement of the [4.5.5.5]fenestrane to a triquinacane skeleton. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.088
• 作为产物：
  描述：

  4-戊烯酰氯 在 乙二胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.67h， 生成 5-<(tert-butyl)dimethylsilyloxy>-5-(ethynyl)nona-1,8-diene
  参考文献：
  名称：

  The TandemPauson-Khand Reaction

  摘要：

  AbstractThe conditions for the novel tandem Pauson‐Khand reaction have been explored. The highly functionalized tetracyclic compounds 11c, 11d, and 16 were prepared from the ene‐diynes 4c, 4d, and 10 by treatment with 2 equiv. of [Co2(CO)8] and 4‐methylmorpholine N‐oxide (NMO) or Me3NO in yields of 24, 22, and 53%, respectively (Table). In the presence of 1–3 equiv. of H2O added to the NMO used for induction of the Pauson‐Khand reaction of 6d, a mixture of cyclopentanones 17/18 and cyclopentenones 12/13 was obtained (Scheme 5). The first example of a [Co2(CO)6]‐induced highly stereoselective ene reaction is described. To account for these results, the formation of intermediates are proposed (Schemes 6 and 7) which hitherto have not been considered in the mechanistic description of the Pauson‐Khand reaction.

  DOI：

  10.1002/hlca.19960790214

文献信息

• A cis,trans,cis,cis-[4.5.5.5]Fenestrane Derivative
  作者：M. Thommen、R. Keese、M. Förtsch

  DOI：10.1107/s0108270196002120

  日期：1996.8.15

  The title compound, rel-(1R,4R,7S,10R)-7-(tert-butyldimethylsilyloxy)tetracyclo [5.4.1.0(4,12).0(10,12)]dodecan-2-one, C18H30O2Si, has been prepared and its structure determined. The geometry of the central C(C)(4) substructure of the fenestrane skeleton shows a considerable distortion from an ideal tetrahedral arrangement towards planarity. Values of 127.0 (2) and 131.1(2)degrees are observed for the bond angles at the bridgehead atoms of the trans-bicyclo[3.3.0]octane subunit.