methyl (Z)-7-((tetrahydro-2H-pyran-2-yl)oxy)hept-5-enoate | 81893-16-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-7-((tetrahydro-2H-pyran-2-yl)oxy)hept-5-enoate
• CAS: 81893-16-5
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: XRFNRKJLXZABFX-UTCJRWHESA-N

物化性质

• 沸点：
  336.6±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-7-((tetrahydro-2H-pyran-2-yl)oxy)hept-5-enoate 在 四溴化碳 、 camphor-10-sulfonic acid 、 三苯基膦 、 sodium iodide 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 生成 甲基(5Z)-7-[(3R)-3-羟基-5-氧代-1-环戊烯-1-基]-5-庚烯酸酯
  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
• 作为产物：
  描述：

  methyl 7-(2'-tetrahydropyranyloxy)-5-heptynoate 在 Lindlar's catalyst 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 methyl (Z)-7-((tetrahydro-2H-pyran-2-yl)oxy)hept-5-enoate
  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