5-<4(E)-5-(Methoxycarbonyl)pent-4-enyl>-2-methyl-2-cyclohexen-1-one | 165316-65-4

• 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: 5-<4(E)-5-(Methoxycarbonyl)pent-4-enyl>-2-methyl-2-cyclohexen-1-one
• 英文别名: methyl (E)-6-(4-methyl-5-oxocyclohex-3-en-1-yl)hex-2-enoate
• CAS: 165316-65-4
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: QLTDAOCCOLFHCX-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  6
• 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：

  5-<4(E)-5-(Methoxycarbonyl)pent-4-enyl>-2-methyl-2-cyclohexen-1-one 在 二异丁基氢化铝 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 为溶剂， 反应 2.0h， 生成 (1R*,2S*,3S*,7S*,8R*,10S*)-2-(Hydroxymethyl)-10-methyltricyclo<5.3.1.0^3,8>undecan-9-ol
  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-methylcyclohex-2-en-1-one 在 sodium tetrahydroborate 、 高氯酸 、 cerium(III) chloride 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 40.5h， 生成 5-<4(E)-5-(Methoxycarbonyl)pent-4-enyl>-2-methyl-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.