Methyl 7-(6-oxo-1-cyclohexenyl)-5-heptynoate | 132570-81-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 7-(6-oxo-1-cyclohexenyl)-5-heptynoate
• 英文别名: Methyl 7-(6-oxocyclohex-1-EN-1-YL)hept-5-ynoate；methyl 7-(6-oxocyclohexen-1-yl)hept-5-ynoate
• CAS: 132570-81-1
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: SREYRUJLDIYIQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 7-iodohept-5-ynoate 、 2-(Phenylseleno)-2-cyclohexenone 生成 Methyl 7-(6-oxo-1-cyclohexenyl)-5-heptynoate
  参考文献：
  名称：

  A novel vinyl anion equivalent. An extremely short synthesis of 2-substituted 2-cycloalkenones and prostaglandin key intermediates via destannylselenenylation

  摘要：

  The preparation of a novel vinyl anion equivalent and a new destannylselenenylation procedure are described. The conjugate addition of (tributylstannyl)lithium to 2-(phenylseleno)-2-cycloalkenones, followed by the trapping of the resulting enolates with allylic halides, and subsequent destannylselenenylation gives 2-substituted 2-cycloalkenones in high yields, in a one-pot procedure. The destannylselenenylation can be successfully performed under a variety of conditions: treatments with fluoride, bases, Lewis acids, or silica gel as well as thermal or photochemical treatments are effective. Following the described method, chiral prostaglandin E2 key intermediates were obtained in one pot from chiral 4-[(tert-butyldimethylsilyl)oxy]-2-(phenylseleno)-2-cyclopentenone.

  DOI：

  10.1021/jo00037a035

文献信息

• A novel vinyl anion equivalent. An extremely short synthesis of 2-substituted 2-cycloalkenones and prostaglandin key intermediates via destannylselenenylation
  作者：Shinya Kusuda、Yoshihiko Watanabe、Yoshio Ueno、Takeshi Toru

  DOI：10.1021/jo00037a035

  日期：1992.5

  The preparation of a novel vinyl anion equivalent and a new destannylselenenylation procedure are described. The conjugate addition of (tributylstannyl)lithium to 2-(phenylseleno)-2-cycloalkenones, followed by the trapping of the resulting enolates with allylic halides, and subsequent destannylselenenylation gives 2-substituted 2-cycloalkenones in high yields, in a one-pot procedure. The destannylselenenylation can be successfully performed under a variety of conditions: treatments with fluoride, bases, Lewis acids, or silica gel as well as thermal or photochemical treatments are effective. Following the described method, chiral prostaglandin E2 key intermediates were obtained in one pot from chiral 4-[(tert-butyldimethylsilyl)oxy]-2-(phenylseleno)-2-cyclopentenone.