(3aR,4S,4aS,8aS,9aR)-5-ethenyl-4-(methoxymethoxy)-2,2-dimethyl-4,4a,7,8,8a,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-9-one | 250224-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4S,4aS,8aS,9aR)-5-ethenyl-4-(methoxymethoxy)-2,2-dimethyl-4,4a,7,8,8a,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-9-one
• CAS: 250224-19-2
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: GANBXXUAVFUZEY-PTNZTPPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,4S,4aS,8aS,9aR)-5-ethenyl-4-(methoxymethoxy)-2,2-dimethyl-4,4a,7,8,8a,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-9-one 、 1-环戊烯-1,2-二羧酸酐 以 苯 为溶剂， 反应 144.0h， 以83%的产率得到(1S,2S,5S,7R,11R,12S,13S,17R)-12-(methoxymethoxy)-9,9-dimethyl-8,10,19-trioxahexacyclo[15.3.3.01,17.02,14.05,13.07,11]tricos-14-ene-6,18,20-trione
  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 、 4-二甲氨基吡啶 、 indium 、 草酰氯 、 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 、 硫酸 、 四丁基氟化铵 、 氨 、 sodium 、 copper(II) sulfate 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (3aR,4S,4aS,8aS,9aR)-5-ethenyl-4-(methoxymethoxy)-2,2-dimethyl-4,4a,7,8,8a,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-9-one
  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

• A Diene Transmissive Diels−Alder Strategy for Oxygenated Nor-Steroid and Triterpenoid Skeletons
  作者：Simon Woo、Stéphanie Legoupy、Stéphanie Parra、Alex G. Fallis

  DOI：10.1021/ol990798v

  日期：1999.10.1

  [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.