(2R,3S)-2-[(E)-but-2-enoxy]-3-phenylselanyloxolane | 300578-39-6

• 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: (2R,3S)-2-[(E)-but-2-enoxy]-3-phenylselanyloxolane
• CAS: 300578-39-6
• 化学式: C₁₄H₁₈O₂Se
• 分子量: 297.256
• InChiKey: WTINHXGFXJPSPL-SZZVUECUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  丙烯腈 、 (2R,3S)-2-[(E)-but-2-enoxy]-3-phenylselanyloxolane 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以78%的产率得到4-[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl]pentanenitrile
  参考文献：
  名称：

  Intermolecular and Intramolecular Reactions of Resolved 2-Alkoxytetrahydrofuran-3-yl and 2-Alkoxytetrahydropyran-3-yl Radicals

  摘要：

  Diastereomeric trans-2-alkoxy-3-phenylselenenyltetrahydrofuranyl acetals and trans-2-alkoxy-3-phenyl-selenenyltetrahydropyranyl acetals were prepared from dihydrofuran, dihydropyran, phenylselenenyl bromide, and the alcohols (S)-methyl lactate, (S)-methyl hexahydromandelate, and (R)-pantolactone. The diastereomers were chromatographically separated and were subjected to intermolecular alkylation via generation and trapping of free radicals. Observed diastereoselectivity was higher for 2-alkoxytetrahydrofuran-3-yl radicals than for 2-alkoxytetrahydropyran-3-yl radicals, and highest for acetals involving (R)-pantolactone. Alcohol exchanges at the anomeric carbon were highly stereocontrolled, and permitted introduction of alkenes for intramolecular trapping of free radical intermediates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00547-0
• 作为产物：
  描述：

  二苯基二硒醚 在 溴 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S)-2-[(E)-but-2-enoxy]-3-phenylselanyloxolane
  参考文献：
  名称：

  Intermolecular and Intramolecular Reactions of Resolved 2-Alkoxytetrahydrofuran-3-yl and 2-Alkoxytetrahydropyran-3-yl Radicals

  摘要：

  Diastereomeric trans-2-alkoxy-3-phenylselenenyltetrahydrofuranyl acetals and trans-2-alkoxy-3-phenyl-selenenyltetrahydropyranyl acetals were prepared from dihydrofuran, dihydropyran, phenylselenenyl bromide, and the alcohols (S)-methyl lactate, (S)-methyl hexahydromandelate, and (R)-pantolactone. The diastereomers were chromatographically separated and were subjected to intermolecular alkylation via generation and trapping of free radicals. Observed diastereoselectivity was higher for 2-alkoxytetrahydrofuran-3-yl radicals than for 2-alkoxytetrahydropyran-3-yl radicals, and highest for acetals involving (R)-pantolactone. Alcohol exchanges at the anomeric carbon were highly stereocontrolled, and permitted introduction of alkenes for intramolecular trapping of free radical intermediates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00547-0

文献信息

• Intermolecular and Intramolecular Reactions of Resolved 2-Alkoxytetrahydrofuran-3-yl and 2-Alkoxytetrahydropyran-3-yl Radicals
  作者：Kalpana S Nimkar、Eugene A Mash

  DOI：10.1016/s0040-4020(00)00547-0

  日期：2000.8

  Diastereomeric trans-2-alkoxy-3-phenylselenenyltetrahydrofuranyl acetals and trans-2-alkoxy-3-phenyl-selenenyltetrahydropyranyl acetals were prepared from dihydrofuran, dihydropyran, phenylselenenyl bromide, and the alcohols (S)-methyl lactate, (S)-methyl hexahydromandelate, and (R)-pantolactone. The diastereomers were chromatographically separated and were subjected to intermolecular alkylation via generation and trapping of free radicals. Observed diastereoselectivity was higher for 2-alkoxytetrahydrofuran-3-yl radicals than for 2-alkoxytetrahydropyran-3-yl radicals, and highest for acetals involving (R)-pantolactone. Alcohol exchanges at the anomeric carbon were highly stereocontrolled, and permitted introduction of alkenes for intramolecular trapping of free radical intermediates. (C) 2000 Elsevier Science Ltd. All rights reserved.