(2Z)-6-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-hexene | 307497-57-0

• 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: (2Z)-6-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-hexene
• CAS: 307497-57-0
• 化学式: C₂₈H₄₄O₂Si₂
• 分子量: 468.827
• InChiKey: NYYFIBRGDPMVKZ-ZDLGFXPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (2Z)-6-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-hexene 在 4-二甲氨基吡啶 、 disodium hydrogenphosphate 、 4-甲基苯磺酸吡啶 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (2R*,3R*)-1-(tert-butyldiphenylsilyloxy)-6-chloromethanesulfonyloxy-2,3-epoxyhexane
  参考文献：
  名称：

  Transformation of cis-Epoxy Compound to cis-2,3-Disubstituted Oxane and Investigation on Propagation Step in the Ring-Expansion Reactions of cis,trans-Diepoxy Systems

  摘要：

  Conversion of cis-epoxy compounds by successive ring-expansion reaction into trans-fused cyclic ethers was examined from both the initiation step and the propagation step. The ring-expansion reaction of cis-4,5-epoxy compounds containing a leaving group on C-1 was attempted as a unit process for the successive reaction. When a chloromesyl group was used as a leaving group, the ring expansion proceeded to give an oxane derivative (endo-type product) preferentially. On the other hand, investigation of the propagation step was carried out with respect to epoxy oxane derivatives. It was clarified that the ring-expansion reaction of cis-2,3-disubstituted oxane derivatives provided spiro acetals as products, not the desired trans-fused cyclic ethers, owing to the reaction pathway triggered by 1,2-hydride rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00622-0
• 作为产物：
  描述：

  6-(tert-butyldimethylsiloxy)hex-2-yn-1-ol 在 nickel diacetate 、 乙二胺 咪唑 、 sodium hydroxide 、 sodium tetrahydroborate 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (2Z)-6-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-hexene
  参考文献：
  名称：

  Base-Catalyzed Endo-Mode Cyclization of Allenes:  Easy Preparation of Five- to Nine-Membered Oxacycles

  摘要：

  A reliable and efficient procedure for constructing five- to eight-membered oxacycles has been developed. Allenes with both a phosphoryl group and a suitable delta-hydroxyalkyl side chain at the Cl-position underwent an endo mode ring-closing reaction to give five- to seven-membered oxacycles. Changing the phosphoryl group to a phosphono functionality facilitated the preparation of eight-membered congeners. Introduction of a cis double bond to the alkyl side chain of the starting allenes made possible the easy formation of medium-sized oxacycles, such as the dihydrooxocin and tetrahydrooxonin frameworks, regardless of the electron-withdrawing group (POPh2, PO(OEt)(2), SOPh, and SO2Ph) at the C-1-position.

  DOI：

  10.1021/jo0488614