Ethenesulfonic acid (E)-(S)-2-benzyloxy-5-oxo-hex-3-enyl ester | 183795-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethenesulfonic acid (E)-(S)-2-benzyloxy-5-oxo-hex-3-enyl ester
• 英文别名: [(E,2S)-5-oxo-2-phenylmethoxyhex-3-enyl] ethenesulfonate
• CAS: 183795-62-2
• 化学式: C₁₅H₁₈O₅S
• 分子量: 310.371
• InChiKey: DCVNOIDEQFMNOR-FEAKQIBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethenesulfonic acid (E)-(S)-2-benzyloxy-5-oxo-hex-3-enyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 25.0~130.0 ℃ 、1.2 MPa 条件下， 反应 5.0h， 生成 ((4S,8aS)-4-Benzyloxy-1,1-dioxo-3,4,4a,5,8,8a-hexahydro-1H-1λ⁶-benzo[c][1,2]oxathiin-6-yloxy)-tert-butyl-dimethyl-silane
  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：

  乙烯磺酰氯 、 (5S,3E)-5-benzyloxy-6-hydroxy-hex-3-en-2-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到Ethenesulfonic acid (E)-(S)-2-benzyloxy-5-oxo-hex-3-enyl ester
  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

文献信息

• 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.