6-phenyl-2,4-bis((trimethylsilyl)oxy)-1-hexene | 127841-25-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-phenyl-2,4-bis((trimethylsilyl)oxy)-1-hexene
• 英文别名: Trimethyl-(1-phenyl-5-trimethylsilyloxyhex-5-en-3-yl)oxysilane
• CAS: 127841-25-2
• 化学式: C₁₈H₃₂O₂Si₂
• 分子量: 336.622
• InChiKey: SFURGPMCZKALDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  6-phenyl-2,4-bis((trimethylsilyl)oxy)-1-hexene 、 原甲酸三乙酯 生成 5-hydroxy-1,1-dimethoxy-7-phenyl-3-heptanone
  参考文献：
  名称：

  MARTIN, VAN A.;PERRON, FRANCOISE;ALBIZATI, KIM F., TETRAHEDRON LETT., 31,(1990) N, C. 301-304

  摘要：

  DOI：
• 作为产物：
  描述：

  苯丙醛 在 lithium diisopropyl amide 作用下， 反应 1.5h， 生成 6-phenyl-2,4-bis((trimethylsilyl)oxy)-1-hexene
  参考文献：
  名称：

  Van Martin; Murray, Desmond H.; Pratt, Norman E., Journal of the American Chemical Society, 1990, vol. 112, # 19, p. 6965 - 6978

  摘要：

  DOI：

文献信息

• Chemistry of dioxenium cations. Synthetic and mechanistic studies on the stereocontrolled formation of tetrahydropyrans from homoallylic alcohols and ortho esters
  作者：Francoise Perron-Sierra、Michele A. Promo、Van A. Martin、Kim F. Albizati

  DOI：10.1021/jo00021a043

  日期：1991.10

  Despite their long history, dioxenium cations are underutilized reactive synthetic intermediates. It was found that ortho esters and homoallylic alcohols in the presence of Lewis acids provide 4-heterosubstituted pyranosides in a stereoselective manner. The mechanistic course of events was supported by control experiments and synthesis of a putative mixed ortho ester intermediate which exhibited identical reactivity. A transition state for termination of the dioxenium cation-olefin cyclization is proposed, involving intramolecular delivery of chloride by a coordinated tin species. Structure-reactivity relationships indicate that a cation-stabilizing substituent (alkyl or alkoxy) at the internal position of the olefin is required for cyclization. A variety of 3-alkyl-substituted homoallylic alcohols cyclize cleanly to substituted 2-alkoxytetrahydropyrans in good yield. beta-silyloxy silyl enol ethers were found to smoothly provide 4-oxotetrahydropyranosides when subjected to the same reaction conditions. For these substrates, the course of the cyclization proceeds in a different manner involving a rapid intermolecular Mukaiyama aldol condensation followed by transacetalization.
• Chemistry of aldolate dianions. β-Silyloxy silyl enol ethers as bifunctional nucleophilic equivalents for oxygen heterocycle synthesis
  作者：Van A. Martin、Françoise Perron、Kim F. Albizati

  DOI：10.1016/s0040-4039(00)94538-6

  日期：1990.1
• MARTIN, VAN A.;MURRAY, DESMOND H.;PRATT, NORMAN E.;ZHAO, YUN-BO;ALBIZATI,+, J. AMER. CHEM. SOC., 112,(1990) N9, C. 6965-6978
  作者：MARTIN, VAN A.、MURRAY, DESMOND H.、PRATT, NORMAN E.、ZHAO, YUN-BO、ALBIZATI,+

  DOI：——

  日期：——