6-ethyl-5,6-dihydro-3-methylpyran-2-one | 864058-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-ethyl-5,6-dihydro-3-methylpyran-2-one
• 英文别名: (2S)-2-ethyl-5-methyl-2,3-dihydropyran-6-one
• CAS: 864058-44-6
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: NKFQGZUOYWAUNV-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-ethyl-5,6-dihydro-3-methylpyran-2-one 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3R,4R,6S)-3,4-Dibromo-6-ethyl-3-methyl-tetrahydro-pyran-2-one 、 (3S,4S,6S)-3,4-Dibromo-6-ethyl-3-methyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  A Scalable Route to Trisubstituted (E)-Vinyl Bromides

  摘要：

  An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of alpha,beta-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(l 1) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.

  DOI：

  10.1021/ol051376q
• 作为产物：
  描述：

  (S)-3-羟基戊腈 在 正丁基锂 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 17.5h， 生成 6-ethyl-5,6-dihydro-3-methylpyran-2-one
  参考文献：
  名称：

  A Scalable Route to Trisubstituted (E)-Vinyl Bromides

  摘要：

  An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of alpha,beta-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(l 1) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.

  DOI：

  10.1021/ol051376q

文献信息

• A Scalable Route to Trisubstituted (<i>E</i>)-Vinyl Bromides
  作者：Cheon-Gyu Cho、Won-Suk Kim、Amos B. Smith

  DOI：10.1021/ol051376q

  日期：2005.8.1

  An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of alpha,beta-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(l 1) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol.