5-(tert-butyldimethylsilyloxymethyl)-2-methyl-6-phenylhepta-1,6-dien-3-ol | 774603-70-2

• 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: 5-(tert-butyldimethylsilyloxymethyl)-2-methyl-6-phenylhepta-1,6-dien-3-ol
• CAS: 774603-70-2
• 化学式: C₂₁H₃₄O₂Si
• 分子量: 346.585
• InChiKey: BTWDVZHMHOJSIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldimethylsilyloxymethyl)-2-methyl-6-phenylhepta-1,6-dien-3-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三异丙基亚磷酸酯 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 (+/-)-(1'R,4'S)-9-[4-(hydroxymethyl)-2-methyl-4-phenylcyclopent-2-en-1-yl]adenine
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Novel 2′,4′‐Doubly Branched Carbocyclic Nucleosides

  摘要：

  A series of 2' and 4'-doubly branched carbocyclic nucleosides 15, 16, 17 and 18 were synthesized starting from simple acyclic ketone derivatives. The required 4'-quaternary carbon was constructed using Claisen rearrangement. In addition, the installation of a methyl group in the 2'-position was accomplished using a Grignard carbonyl addition of isopropenylmagnesium bromide. Bis-vinyl was successfully cyclized using a Grubbs' catalyst II. Natural bases (adenine, cytosine) were efficiently coupled by using Pd(0) catalyst.

  DOI：

  10.1081/ncn-120039252
• 作为产物：
  描述：

  异丙烯基溴化镁 、 3-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenyl-pent-4-enal 以 四氢呋喃 为溶剂， 反应 3.0h， 以85%的产率得到5-(tert-butyldimethylsilyloxymethyl)-2-methyl-6-phenylhepta-1,6-dien-3-ol
  参考文献：
  名称：

  Synthesis and Antiviral Activity of Novel 2′,4′‐Doubly Branched Carbocyclic Nucleosides

  摘要：

  A series of 2' and 4'-doubly branched carbocyclic nucleosides 15, 16, 17 and 18 were synthesized starting from simple acyclic ketone derivatives. The required 4'-quaternary carbon was constructed using Claisen rearrangement. In addition, the installation of a methyl group in the 2'-position was accomplished using a Grignard carbonyl addition of isopropenylmagnesium bromide. Bis-vinyl was successfully cyclized using a Grubbs' catalyst II. Natural bases (adenine, cytosine) were efficiently coupled by using Pd(0) catalyst.

  DOI：

  10.1081/ncn-120039252