Ethyl 4-<2-<(ethoxycarbonyl)methyl>-3,3-dimethyl-1-cyclohexen-1-yl>butyrate

• 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: Ethyl 4-<2-<(ethoxycarbonyl)methyl>-3,3-dimethyl-1-cyclohexen-1-yl>butyrate
• 英文别名: Ethyl 4-[2-(2-ethoxy-2-oxoethyl)-3,3-dimethylcyclohexen-1-yl]butanoate
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: KBZLYAQBVSKEJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2-二甲基环己酮 在 氯化亚砜 、 sodium hydride 、 magnesium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 54.92h， 生成 Ethyl 4-<2-<(ethoxycarbonyl)methyl>-3,3-dimethyl-1-cyclohexen-1-yl>butyrate
  参考文献：
  名称：

  Retinoids and Related Compounds. 17. Conformational Study of Retinochrome Chromophore: Synthesis of 8,18-Ethanoretinal and a New Retinochrome Analog

  摘要：

  In order to investigate the chromophore conformation around the trimethylcyclohexene ring in retinochrome, (all-E)-8,18-ethanoretinal (2), in which C-8 and C-18 positions of retinal 1 was connected by an ethylene group, was synthesized via the Dieckmann condensation of diester 6 from 2,2-dimethylcyclohexanone 7. This analog 2 was incorporated into aporetinochrome, forming a pigment with lambda(max) at 498 nm. Its opsin shift (2200 cm(-1)) is of the same order of magnitude as that of native retinochrome (2400 cm(-1)), suggesting that the conformations of both chromophores are fairly similar in the protein. In addition, MMX calculations indicate that the torsional angle around the 6-7 single bond in retinochrome might correspond to the allowable torsional angle in 8,18-ethanoretinal (2).

  DOI：

  10.1021/jo00102a015

文献信息

• Retinoids and Related Compounds. 17. Conformational Study of Retinochrome Chromophore: Synthesis of 8,18-Ethanoretinal and a New Retinochrome Analog
  作者：Akimori Wada、Miho Sakai、Tomoya Kinumi、Kazuo Tsujimoto、Masashige Yamauchi、Masayoshi Ito

  DOI：10.1021/jo00102a015

  日期：1994.11

  In order to investigate the chromophore conformation around the trimethylcyclohexene ring in retinochrome, (all-E)-8,18-ethanoretinal (2), in which C-8 and C-18 positions of retinal 1 was connected by an ethylene group, was synthesized via the Dieckmann condensation of diester 6 from 2,2-dimethylcyclohexanone 7. This analog 2 was incorporated into aporetinochrome, forming a pigment with lambda(max) at 498 nm. Its opsin shift (2200 cm(-1)) is of the same order of magnitude as that of native retinochrome (2400 cm(-1)), suggesting that the conformations of both chromophores are fairly similar in the protein. In addition, MMX calculations indicate that the torsional angle around the 6-7 single bond in retinochrome might correspond to the allowable torsional angle in 8,18-ethanoretinal (2).