(4S)-4-[(1E)-3-methylbuta-1,3-dienyl]-2,2-dimethyl-1,3-dioxolane | 183795-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-4-[(1E)-3-methylbuta-1,3-dienyl]-2,2-dimethyl-1,3-dioxolane
• 英文别名: (4S)-2,2-dimethyl-4-[(1E)-3-methylbuta-1,3-dienyl]-1,3-dioxolane
• CAS: 183795-42-8
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: NXNBNNFCNGVKKH-CYNONHLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-苯基-1,2,4-三唑啉-3,5-二酮 、 (4S)-4-[(1E)-3-methylbuta-1,3-dienyl]-2,2-dimethyl-1,3-dioxolane 以 二氯甲烷 为溶剂， 生成 8-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-methyl-2-phenyl-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione
  参考文献：
  名称：

  Chiral dienes from enantiomerically pure enones. Highly stereoselective intramolecular Diels–Alder reaction involving ethenesulfonates

  摘要：

  Chiral dienes 2, easily prepared from alpha,beta-unsaturated gamma-alkoxy ketones, are subjected to inter- and intramolecular Diels-Alder reactions, Intermolecular cycloadditions of dienes 2 with 4-phenyl-1,2,4-triazole-3,5(2H)-dione 3 are found to be diastereoselective, Thermal or high pressure-induced intramolecular cycloadditions of trienes 8, featuring a sulfonate moiety connecting a diene and a dienophile, are found to proceed with high diastereoselectivity to give sultones 11 and 12. An interesting domino process is observed when enone 5 is reacted with sodium hydride. In this reaction sequence, the decahydropyrano [2,3,4-de]chromene derivative 15 was formed, NMR spectroscopic studies allowed the assignments of the configurations of the bi- and tri-cyclic products.

  DOI：

  10.1039/p19960002297
• 作为产物：
  描述：

  双丙酮-D-甘露糖醇 在 potassium metaperiodate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 (4S)-4-[(1E)-3-methylbuta-1,3-dienyl]-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Huang, Jing-Mei; Xu, Kai-Chen; Loh, Teck-Peng, Synthesis, 2003, # 5, p. 755 - 764

  摘要：

  DOI：

文献信息

• Huang, Jing-Mei; Xu, Kai-Chen; Loh, Teck-Peng, Synthesis, 2003, # 5, p. 755 - 764
  作者：Huang, Jing-Mei、Xu, Kai-Chen、Loh, Teck-Peng

  DOI：——

  日期：——
• Chiral dienes from enantiomerically pure enones. Highly stereoselective intramolecular Diels–Alder reaction involving ethenesulfonates
  作者：Guido Galley、Michael Pätzel

  DOI：10.1039/p19960002297

  日期：——

  Chiral dienes 2, easily prepared from alpha,beta-unsaturated gamma-alkoxy ketones, are subjected to inter- and intramolecular Diels-Alder reactions, Intermolecular cycloadditions of dienes 2 with 4-phenyl-1,2,4-triazole-3,5(2H)-dione 3 are found to be diastereoselective, Thermal or high pressure-induced intramolecular cycloadditions of trienes 8, featuring a sulfonate moiety connecting a diene and a dienophile, are found to proceed with high diastereoselectivity to give sultones 11 and 12. An interesting domino process is observed when enone 5 is reacted with sodium hydride. In this reaction sequence, the decahydropyrano [2,3,4-de]chromene derivative 15 was formed, NMR spectroscopic studies allowed the assignments of the configurations of the bi- and tri-cyclic products.