3-(5',7'-bis-tert-butyldimethylsiloxy-6',6'-dimethyl-3'-(S)-methyl-4'-heptenyl)furan | 746657-22-7

• 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: 3-(5',7'-bis-tert-butyldimethylsiloxy-6',6'-dimethyl-3'-(S)-methyl-4'-heptenyl)furan
• 英文别名: tert-butyl-[(Z,5S)-3-[tert-butyl(dimethyl)silyl]oxy-7-(furan-3-yl)-2,2,5-trimethylhept-3-enoxy]-dimethylsilane
• CAS: 746657-22-7
• 化学式: C₂₆H₅₀O₃Si₂
• 分子量: 466.852
• InChiKey: OYJZFKGHJTWOPL-ABCSWIFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5',7'-bis-tert-butyldimethylsiloxy-6',6'-dimethyl-3'-(S)-methyl-4'-heptenyl)furan 在 咪唑 、 2,6-二甲基吡啶 、 碘 、 lithium perchlorate 、 对甲苯磺酸 、 silver nitrate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 Δ4,11-1S,5S,9R-13(R,S)-methoxy-8-oxo-4,9-deoxy-12-noralliacol
  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：

  (E)-1-(tert-Butyl-dimethyl-silanyloxy)-7-furan-3-yl-2,2-dimethyl-hept-4-en-3-one 在 copper(II) bis(trifluoromethanesulfonate) 、 三乙胺 、 N,N-dimethyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 51.0h， 生成 3-(5',7'-bis-tert-butyldimethylsiloxy-6',6'-dimethyl-3'-(S)-methyl-4'-heptenyl)furan
  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

文献信息

• Oxidative Cyclizations:  The Asymmetric Synthesis of (−)-Alliacol A
  作者：John Mihelcic、Kevin D. Moeller

  DOI：10.1021/ja048085h

  日期：2004.7.1

  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.