6-<5(E)-6-(Methoxycarbonyl)hex-5-enyl>-2-cyclohexen-1-one | 165316-57-4

• 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: 6-<5(E)-6-(Methoxycarbonyl)hex-5-enyl>-2-cyclohexen-1-one
• 英文别名: methyl (E)-7-(2-oxocyclohex-3-en-1-yl)hept-2-enoate
• CAS: 165316-57-4
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: OZORUCZYLTXEJQ-VZUCSPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-<5(E)-6-(Methoxycarbonyl)hex-5-enyl>-2-cyclohexen-1-one 在 lithium hexamethyldisilazane 作用下， 以 乙醚 、 正己烷 为溶剂， 以68%的产率得到(1R*,6R*,7S*,8R*)-7-(Methoxycarbonyl)tricyclo<6.2.2.0^1,6>dodecan-10-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：

  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

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.