6-(5-羟基戊基)环己-2-烯-1-酮 | 90122-56-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 6-(5-羟基戊基)环己-2-烯-1-酮
• 英文名称: 6-(5-hydroxypentyl)cyclohex-2-enone
• 英文别名: 6-(5-Hydroxypentyl)-2-cyclohexen-1-one；6-(5-Hydroxypentyl)cyclohex-2-EN-1-one
• CAS: 90122-56-8
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: FPGNVCIALHKCJI-UHFFFAOYSA-N

物化性质

• 沸点：
  312.9±21.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(5-羟基戊基)环己-2-烯-1-酮 在 重铬酸吡啶 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 6-<5(E)-6-(Methoxycarbonyl)hex-5-enyl>-2-cyclohexen-1-one
  参考文献：
  名称：

  Stereoselective Formation of Three Carbon-Carbon Bonds by Cascade Reaction with Enolate Anion: Synthesis of Tricyclo[6.2.2.01,6]dodecane and Tricyclo[5.3.1.03,8]undecane Derivatives

  摘要：

  Reaction of 6-[5(E)-6-(methoxycarbonyl)hex-5-enyl]-2-cyclohexen-1-one (1) with LHMDS, followed by one-pot treatment with CH2O, resulted in a cascade Michael-Michael-aldol reaction, producing hydroxymethylated tricyclo[6.2.2.0(1,6)]dodecane 3. The methylated tricyclo[5.3.1.0(3,8)]undecane 21 was obtained by a Michael-Michael-substitution reaction, performed by reaction of 5-[4(E)-5(methoxycarbonyl)pent-4-enyl]-2-methyl-2-cyclohexen-1-one (11) with LHMDS and one-pot treatment with MeI in the presence of HMPA. Michael-Michael-aldol reactions of 11 were also carried out with LHMDS followed by several aldehydes to provide tricyclo[5.3.1.0(3,8)]undecane derivatives 22, 23, and 24, respectively. The importance of intramolecular coordination wit h lithium for the double Michael reaction was supported by an experiment utilizing the corresponding (Z)-isomer 13.

  DOI：

  10.1021/jo00099a034
• 作为产物：
  描述：

  5-(2-methoxyphenyl)pent-4-en-1-ol 在 盐酸 、 氨 、 lithium 、 异丙醇 作用下， 生成 6-(5-羟基戊基)环己-2-烯-1-酮
  参考文献：
  名称：

  Ihara, Masataka; Toyota, Masahiro; Abe, Mariko, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1543 - 1550

  摘要：

  DOI：

文献信息

• Ihara Masataka, Makita Kei, Tokunaga Yuji, Fukumoto Keiichiro, J. Org. Chem., 59 (1994) N 20, S 6008-6013
  作者：Ihara Masataka, Makita Kei, Tokunaga Yuji, Fukumoto Keiichiro

  DOI：——

  日期：——
• Stereoselective Formation of Three Carbon-Carbon Bonds by Cascade Reaction with Enolate Anion: Synthesis of Tricyclo[6.2.2.01,6]dodecane and Tricyclo[5.3.1.03,8]undecane Derivatives
  作者：Masataka Ihara、Kei Makita、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo00099a034

  日期：1994.10

  Reaction of 6-[5(E)-6-(methoxycarbonyl)hex-5-enyl]-2-cyclohexen-1-one (1) with LHMDS, followed by one-pot treatment with CH2O, resulted in a cascade Michael-Michael-aldol reaction, producing hydroxymethylated tricyclo[6.2.2.0(1,6)]dodecane 3. The methylated tricyclo[5.3.1.0(3,8)]undecane 21 was obtained by a Michael-Michael-substitution reaction, performed by reaction of 5-[4(E)-5(methoxycarbonyl)pent-4-enyl]-2-methyl-2-cyclohexen-1-one (11) with LHMDS and one-pot treatment with MeI in the presence of HMPA. Michael-Michael-aldol reactions of 11 were also carried out with LHMDS followed by several aldehydes to provide tricyclo[5.3.1.0(3,8)]undecane derivatives 22, 23, and 24, respectively. The importance of intramolecular coordination wit h lithium for the double Michael reaction was supported by an experiment utilizing the corresponding (Z)-isomer 13.
• Ihara, Masataka; Toyota, Masahiro; Abe, Mariko, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1543 - 1550
  作者：Ihara, Masataka、Toyota, Masahiro、Abe, Mariko、Ishida, Yohhei、Fukumoto, Keiichiro、Kametani, Tetsuji

  DOI：——

  日期：——