1,1-Dimethyl-1,2,3,4,6,7,8,9-octahydro-5H-benzocyclohepten-8-one | 147590-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-Dimethyl-1,2,3,4,6,7,8,9-octahydro-5H-benzocyclohepten-8-one
• 英文别名: 4,4-dimethyl-2,3,5,7,8,9-hexahydro-1H-benzo[7]annulen-6-one
• CAS: 147590-55-4
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: WCTGUBIMILKTNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  1,1-Dimethyl-1,2,3,4,6,7,8,9-octahydro-5H-benzocyclohepten-8-one 在 正丁基锂 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 12.0h， 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
• 作为产物：
  描述：

  2,2-二甲基环己酮 在 氯化亚砜 、 potassium tert-butylate 、 sodium hydride 、 magnesium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 12.0h， 生成 1,1-Dimethyl-1,2,3,4,6,7,8,9-octahydro-5H-benzocyclohepten-8-one
  参考文献：
  名称：

  Synthesis of 818-ethanoretinal and its interaction with apo-retinochrome

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)77494-6

文献信息

• 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).