hexadec-7-ynal | 51824-09-0

• 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: hexadec-7-ynal
• CAS: 51824-09-0
• 化学式: C₁₆H₂₈O
• 分子量: 236.398
• InChiKey: CNTLWEVFZAYUJB-UHFFFAOYSA-N

物化性质

• 沸点：
  331.8±25.0 °C(Predicted)
• 密度：
  0.865±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  hexadec-7-ynal 在 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 以77%的产率得到(E)-1-cycloheptenylnonan-1-one
  参考文献：
  名称：

  Brønsted Acid-Promoted Intramolecular Carbocyclization of Alkynals Leading to Cyclic Enones

  摘要：

  TFA-promoted exo carbocyclizations of nonterminal 7-alkynals gave good to excellent yields of seven-membered cycloalkenones, a medium-sized functionalized ring present in natural products with relevant pharmacological properties. Nonterminal 5- and 6-alkynals also gave very good yields of the corresponding exo cyclopentenones and cyclohexenones. On the other hand, terminal 5-alkynals gave endo carbocyclizations to cyclohexenones. These carbocyclizations can be considered as tandem alkyne hydration/aldol condensation processes.

  DOI：

  10.1021/ol900142r
• 作为产物：
  描述：

  7-十六-1-醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到hexadec-7-ynal
  参考文献：
  名称：

  Brønsted Acid-Promoted Intramolecular Carbocyclization of Alkynals Leading to Cyclic Enones

  摘要：

  TFA-promoted exo carbocyclizations of nonterminal 7-alkynals gave good to excellent yields of seven-membered cycloalkenones, a medium-sized functionalized ring present in natural products with relevant pharmacological properties. Nonterminal 5- and 6-alkynals also gave very good yields of the corresponding exo cyclopentenones and cyclohexenones. On the other hand, terminal 5-alkynals gave endo carbocyclizations to cyclohexenones. These carbocyclizations can be considered as tandem alkyne hydration/aldol condensation processes.

  DOI：

  10.1021/ol900142r

文献信息

• Brønsted Acid-Promoted Intramolecular Carbocyclization of Alkynals Leading to Cyclic Enones
  作者：Carlos González-Rodríguez、Luz Escalante、Jesús A. Varela、Luis Castedo、Carlos Saá

  DOI：10.1021/ol900142r

  日期：2009.4.2

  TFA-promoted exo carbocyclizations of nonterminal 7-alkynals gave good to excellent yields of seven-membered cycloalkenones, a medium-sized functionalized ring present in natural products with relevant pharmacological properties. Nonterminal 5- and 6-alkynals also gave very good yields of the corresponding exo cyclopentenones and cyclohexenones. On the other hand, terminal 5-alkynals gave endo carbocyclizations to cyclohexenones. These carbocyclizations can be considered as tandem alkyne hydration/aldol condensation processes.