(1S)-3-ethenyl-1-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(methoxymethoxy)pent-4-en-2-ol | 250224-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-3-ethenyl-1-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(methoxymethoxy)pent-4-en-2-ol
• CAS: 250224-15-8
• 化学式: C₁₅H₂₆O₆
• 分子量: 302.368
• InChiKey: URBSOTHWEBUPSW-FTKZKSHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S)-3-ethenyl-1-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(methoxymethoxy)pent-4-en-2-ol 在 4-二甲氨基吡啶 、 草酰氯 、 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-1-((4S,5R)-5-((S)-1-(methoxymethoxy)-3-vinylpenta-2,4-dien-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylprop-2-en-1-ol
  参考文献：
  名称：

  A Diene Transmissive Diels−Alder Strategy for Oxygenated Nor-Steroid and Triterpenoid Skeletons

  摘要：

  [GRAPHICS]A diene transmissive cycloaddition strategy for the synthesis of tetracyclic skeletons is described, Initially both L-gulonolactone and L-arabinose were converted independently to related acetal aldehydes 13 and 14, A pentadienyl indium reagent supplied the triene unit for 16. The cisisopropylidene acetal controlled the initial intramolecular [4 + 2] cycloaddition to the decalin 21, and a second (tandem) intermolecular cyclization afforded highly oxygenated nor-steroid and triterpenoid skeletons as chiral nonracemic compounds.

  DOI：

  10.1021/ol990798v
• 作为产物：
  描述：

  L-(+)-arabinose 在 盐酸 、 indium 、 硫酸 、 氨 、 sodium 、 copper(II) sulfate 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (1S)-3-ethenyl-1-[(4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(methoxymethoxy)pent-4-en-2-ol
  参考文献：
  名称：

  A Diene Transmissive Diels−Alder Strategy for Oxygenated Nor-Steroid and Triterpenoid Skeletons

  摘要：

  [GRAPHICS]A diene transmissive cycloaddition strategy for the synthesis of tetracyclic skeletons is described, Initially both L-gulonolactone and L-arabinose were converted independently to related acetal aldehydes 13 and 14, A pentadienyl indium reagent supplied the triene unit for 16. The cisisopropylidene acetal controlled the initial intramolecular [4 + 2] cycloaddition to the decalin 21, and a second (tandem) intermolecular cyclization afforded highly oxygenated nor-steroid and triterpenoid skeletons as chiral nonracemic compounds.

  DOI：

  10.1021/ol990798v

文献信息

• Indium-Mediated γ-Pentadienylation of Aldehydes and Ketones:  Cross-Conjugated Trienes for Diene-Transmissive Cycloadditions
  作者：Simon Woo、Neil Squires、Alex G. Fallis

  DOI：10.1021/ol990695c

  日期：1999.8.1

  [GRAPHICS]Treatment of 5-bromo-1,3-pentadiene with indium metal in the presence of carbonyl compounds results in gamma-pentadienylation to generate the 1,4-diene. Elimination of the resulting alcohol affords cross conjugated triene systems which rapidly react with appropriate dienophiles to give tandem intermolecular Diels-Alder adducts.