9-trans-10-13C-β-ionolidenacetonitrile | 87355-35-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 9-trans-10-13C-β-ionolidenacetonitrile
• 英文别名: [2-13C]-3-methyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile；(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)(213C)penta-2,4-dienenitrile
• CAS: 87355-35-9
• 化学式: C₁₅H₂₁N
• 分子量: 216.327
• InChiKey: YOYODHNOTKUUDY-LOBMJLJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  9-trans-10-13C-β-ionolidenacetonitrile 、 碘甲烷 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 [2-13C]-2,3-dimethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile 、 [2-13C]-2,3-dimethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile
  参考文献：
  名称：

  Simple and Efficient Preparation of [10,20-¹³C₂]- and [10-CH₃,13-¹³C₂]-10-Methylretinal:  Introduction of Substituents at the 2-Position of 2,3-Unsaturated Nitriles

  摘要：

  In this paper, we present the synthesis of [10,20-C-13(2)] -10-methylretinal and [10-CH3,13-C-13(2)] -10-methylretinal, two doubly C-13-labeled chemically modified retinals that have been recently used to study the structural and functional details behind the photocascade of bovine rhodopsin (Verdegem et al. Biochemistry 1999, 38, 11316; de Lange et al. Biochemistry 1998, 37, 1411). To obtain both doubly C-13-labeled compounds, we developed a novel synthetic method to directly and regiospecifically introduce a methyl substituent on the 2-position of 3-methyl-5-(2',6',6'-trimethyl-1'cyclohexen-1'-yl)-2,4-pentadienenitrile. Encouraged by these results, we investigated the scope of this novel reaction by developing a general method for the introduction of a variety of substituents to the 2-position of 3-methyl-2,3-unsaturated nitriles, paving the way for simple and efficient synthesis of a wide variety of 10-, 14-, and 10,14-substituted chemically modified retinals, and other biologically important compounds.

  DOI：

  10.1021/jo0009595
• 作为产物：
  描述：

  beta-紫罗酮 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 9-trans-10-13C-β-ionolidenacetonitrile
  参考文献：
  名称：

  Pardoen, J. A.; Neijenesch, H. N.; Mulder, P. P. J., Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, # 7-8, p. 341 - 347

  摘要：

  DOI：

文献信息

• Simple and Efficient Preparation of [10,20-¹³C₂]- and [10-CH₃,13-¹³C₂]-10-Methylretinal:  Introduction of Substituents at the 2-Position of 2,3-Unsaturated Nitriles
  作者：Peter J. E. Verdegem、Menno C. F. Monnee、Johan Lugtenburg

  DOI：10.1021/jo0009595

  日期：2001.2.1

  In this paper, we present the synthesis of [10,20-C-13(2)] -10-methylretinal and [10-CH3,13-C-13(2)] -10-methylretinal, two doubly C-13-labeled chemically modified retinals that have been recently used to study the structural and functional details behind the photocascade of bovine rhodopsin (Verdegem et al. Biochemistry 1999, 38, 11316; de Lange et al. Biochemistry 1998, 37, 1411). To obtain both doubly C-13-labeled compounds, we developed a novel synthetic method to directly and regiospecifically introduce a methyl substituent on the 2-position of 3-methyl-5-(2',6',6'-trimethyl-1'cyclohexen-1'-yl)-2,4-pentadienenitrile. Encouraged by these results, we investigated the scope of this novel reaction by developing a general method for the introduction of a variety of substituents to the 2-position of 3-methyl-2,3-unsaturated nitriles, paving the way for simple and efficient synthesis of a wide variety of 10-, 14-, and 10,14-substituted chemically modified retinals, and other biologically important compounds.
• Pardoen, J. A.; Neijenesch, H. N.; Mulder, P. P. J., Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, # 7-8, p. 341 - 347
  作者：Pardoen, J. A.、Neijenesch, H. N.、Mulder, P. P. J.、Lugtenburg, J.

  DOI：——

  日期：——