(S)-1-(tert-Butyl-dimethyl-silanyloxy)-7-furan-3-yl-2,2,5-trimethyl-heptan-3-one | 746657-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (S)-1-(tert-Butyl-dimethyl-silanyloxy)-7-furan-3-yl-2,2,5-trimethyl-heptan-3-one
• CAS: 746657-20-5
• 化学式: C₂₀H₃₆O₃Si
• 分子量: 352.59
• InChiKey: QQUIAXGPCUYDHA-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(tert-Butyl-dimethyl-silanyloxy)-7-furan-3-yl-2,2,5-trimethyl-heptan-3-one 在 2,6-二甲基吡啶 、 lithium perchlorate 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 36.0h， 生成 3-(tert-Butyl-dimethyl-silanyloxy)-1-((6S,7R)-2-methoxy-6-methyl-2,4,5,6,7,7a-hexahydro-benzofuran-7-yl)-2,2-dimethyl-propan-1-one
  参考文献：
  名称：

  Oxidative Cyclizations:  The Asymmetric Synthesis of (−)-Alliacol A

  摘要：

  A tandem anodic coupling-Friedel-Crafts alkylation strategy has been used to rapidly complete the asymmetric synthesis of alliacol A. The anodic oxidation reaction allowed for the generation of a new bond between two nucleophiles. In the synthesis, the absolute stereochemistry of the final natural product is set relative to a methyl group that is incorporated early in the sequence using an asymmetric Michael reaction.

  DOI：

  10.1021/ja048085h
• 作为产物：
  描述：

  1-bromo-4-hydroxy-3,3-dimethylbutan-2-one 在 2,6-二甲基吡啶 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 、 N,N-dimethyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 17.0h， 生成 (S)-1-(tert-Butyl-dimethyl-silanyloxy)-7-furan-3-yl-2,2,5-trimethyl-heptan-3-one
  参考文献：
  名称：

  Oxidative Cyclizations:  The Asymmetric Synthesis of (−)-Alliacol A

  摘要：

  A tandem anodic coupling-Friedel-Crafts alkylation strategy has been used to rapidly complete the asymmetric synthesis of alliacol A. The anodic oxidation reaction allowed for the generation of a new bond between two nucleophiles. In the synthesis, the absolute stereochemistry of the final natural product is set relative to a methyl group that is incorporated early in the sequence using an asymmetric Michael reaction.

  DOI：

  10.1021/ja048085h