(3E,5E,7E)-1-chloro-6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-3,5,7-trien-2-one | 189136-39-8

• 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: (3E,5E,7E)-1-chloro-6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-3,5,7-trien-2-one
• CAS: 189136-39-8
• 化学式: C₁₈H₂₅ClO
• 分子量: 292.849
• InChiKey: UVACQDBVKAOOSW-IACVHOPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (3E,5E,7E)-1-chloro-6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-3,5,7-trien-2-one 在 正丁基锂 、 sodium iodide 作用下， 以 水 、 丙酮 为溶剂， 反应 6.42h， 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
• 作为产物：
  描述：

  氯碘甲烷 、 N-methoxy-N,5-dimethyl-7-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6-heptanetrienamide 在 甲基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以87%的产率得到(3E,5E,7E)-1-chloro-6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-3,5,7-trien-2-one
  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