Acetic acid (3E,5E,7E)-2-[1-cyano-meth-(Z)-ylidene]-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trienyl ester | 189136-41-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Acetic acid (3E,5E,7E)-2-[1-cyano-meth-(Z)-ylidene]-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trienyl ester
• CAS: 189136-41-2
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: YDZSWTCTCZWXBE-XTJWFEJOSA-N

物化性质

• 沸点：
  497.5±28.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3E,5E,7E)-2-[1-cyano-meth-(Z)-ylidene]-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trienyl ester 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 0.17h， 以70%的产率得到3-(hydroxymethyl)-7-methyl-9-(2,6,6-trimethylcyclohexenyl)-2,4,6,8-nonatetraenenitrile
  参考文献：
  名称：

  Synthesis of 19-Fluororetinal and 20-Fluororetinal

  摘要：

  We have investigated methods to monofluorinate the methyl positions 19 and 20 in retinal, and we describe a general, mild strategy that proceeds in high yields and is compatible with current carbon-13 labeling strategies. The new sequence consists of the conversion of N-methoxy-N-methylamides via the alpha-chloromethyl ketone to the corresponding gamma-hydroxy nitrile, which can subsequently be fluorinated by (diethylamido)sulfur trifluoride (DAST).

  DOI：

  10.1021/jo970162m
• 作为产物：
  描述：

  N-methoxy-N,5-dimethyl-7-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6-heptanetrienamide 在 正丁基锂 、 甲基锂 、 sodium iodide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 6.67h， 生成 Acetic acid (3E,5E,7E)-2-[1-cyano-meth-(Z)-ylidene]-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trienyl ester
  参考文献：
  名称：

  Synthesis of 19-Fluororetinal and 20-Fluororetinal

  摘要：

  We have investigated methods to monofluorinate the methyl positions 19 and 20 in retinal, and we describe a general, mild strategy that proceeds in high yields and is compatible with current carbon-13 labeling strategies. The new sequence consists of the conversion of N-methoxy-N-methylamides via the alpha-chloromethyl ketone to the corresponding gamma-hydroxy nitrile, which can subsequently be fluorinated by (diethylamido)sulfur trifluoride (DAST).

  DOI：

  10.1021/jo970162m