8-Acetyl-1,1-dimethyl-1,2,3,4,6,7-hexahydro-5H-benzocycloheptene | 147590-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-Acetyl-1,1-dimethyl-1,2,3,4,6,7-hexahydro-5H-benzocycloheptene
• 英文别名: 1-(4,4-Dimethyl-1,2,3,7,8,9-hexahydrobenzo[7]annulen-6-yl)ethanone
• CAS: 147590-57-6
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: JEHUNZZNZGVBCI-UHFFFAOYSA-N

物化性质

• 沸点：
  345.6±11.0 °C(predicted)
• 密度：
  0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  8-Acetyl-1,1-dimethyl-1,2,3,4,6,7-hexahydro-5H-benzocycloheptene 在 正丁基锂 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.67h， 生成 methyl (2Z,4E,6E)-7-(4,4-dimethyl-1,2,3,7,8,9-hexahydrobenzo[7]annulen-6-yl)-3-methylocta-2,4,6-trienoate
  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
• 作为产物：
  描述：

  2,2-二甲基环己酮 在 正丁基锂 、 cerium(III) chloride 、 sodium hydride 、 magnesium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 66.75h， 生成 8-Acetyl-1,1-dimethyl-1,2,3,4,6,7-hexahydro-5H-benzocycloheptene
  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

• A new rhodopsin analog involving 11Z-8,18-ethanoretinal as a chromophore.
  作者：Akimori WADA、Miho SAKAI、Yasushi IMAMOTO、Yoshinori SHICHIDA、Toru YOSHIZAWA、Masayoshi ITO

  DOI：10.1248/cpb.41.793

  日期：——

  11Z-8, 18-Ethanoretinal was synthesized from the β-ionone alaog (5) via the Witting reaction, and its binding experiment with bovine opsin afforded the new rhodopsin analog, whose opsin shift and CD spectrum were similar to those of the native rhodopsin.

  11Z-8，18-Ethanoretinal 是由β-酮 alaog（5）通过 Witting 反应合成的，其与牛视网膜蛋白的结合实验得到了新的视网膜蛋白类似物，其视网膜移位和 CD 光谱与原生视网膜蛋白相似。
• Synthesis of 818-ethanoretinal and its interaction with apo-retinochrome
  作者：Akimori Wada、Miho Sakai、Tomoya Kinumi、Kazuo Tsujimoto、Masayoshi Ito

  DOI：10.1016/s0040-4039(00)77494-6

  日期：1993.2

  All-(E)-8,18-ethanoretinal was synthesized from 2,2-dimethylcyclohexanone, and its binding experiment with apo-retinochrome afforded the new retinochrome analog, whose opsin shift exhibited fairly similar to that of the natural retinochrome.
• 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).