(2E)-3-(1,1-Dimethyl-1,2,3,4,6,7-hexahydro-5H-benzocyclohepten-8-yl)-2-butenenitrile | 160481-98-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2E)-3-(1,1-Dimethyl-1,2,3,4,6,7-hexahydro-5H-benzocyclohepten-8-yl)-2-butenenitrile
• 英文别名: (E)-3-(4,4-dimethyl-1,2,3,7,8,9-hexahydrobenzo[7]annulen-6-yl)but-2-enenitrile
• CAS: 160481-98-1
• 化学式: C₁₇H₂₃N
• 分子量: 241.376
• InChiKey: LYQABFBZXZCCOM-UKTHLTGXSA-N

物化性质

• 沸点：
  398.348±11.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.986±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E)-3-(1,1-Dimethyl-1,2,3,4,6,7-hexahydro-5H-benzocyclohepten-8-yl)-2-butenenitrile 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.67h， 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 72.75h， 生成 (2E)-3-(1,1-Dimethyl-1,2,3,4,6,7-hexahydro-5H-benzocyclohepten-8-yl)-2-butenenitrile
  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).