[(3E,5E,7E)-3-[(E)-1-cyanoprop-1-en-2-yl]-6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-3,5,7-trienyl] 4-methylbenzenesulfonate | 144736-18-5

• 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: [(3E,5E,7E)-3-[(E)-1-cyanoprop-1-en-2-yl]-6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-3,5,7-trienyl] 4-methylbenzenesulfonate
• CAS: 144736-18-5
• 化学式: C₂₉H₃₇NO₃S
• 分子量: 479.684
• InChiKey: XXDJKSZIUIAVTD-QGDXZVSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  67.16
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(3E,5E,7E)-3-[(E)-1-cyanoprop-1-en-2-yl]-6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-3,5,7-trienyl] 4-methylbenzenesulfonate 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以92%的产率得到3,7-dimethyl-4-(2-azidoethyl)-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,6,8-tetraenenitrile
  参考文献：
  名称：

  Synthesis and vibrational analysis of a locked 14-s-cis conformer of retinal.

  摘要：

  A 12-N-ethano retinal Schiff base is synthesized to study the vibrational properties of a C-14-C-15 s-cis conformer of retinal. The synthesis of the 12-N-ethano retinal Schiff base and seven of its isotopomers is described. Raman and FTIR spectra of this compound and its isotopic derivatives are analyzed and the normal mode assignments compared to MNDO normal coordinate calculations. The frequency of the C-14-C-15 stretch at 1096 cm-1 is approximately 100 cm-1 below typical values for s-trans conformers of retinal polyenes, supporting previous arguments that s-cis conformers will have characteristically low frequencies for the C-C stretch of the s-cis bond (Smith et al., Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 967-971). Deuteriation at the 15-position produces two modes at 950 and 1044 cm-1 that contain C-15D rock character. The elevated frequency (1044 cm-1) of the high-frequency component is a marker band for the C=N syn geometry and confirms an earlier analysis of the sensitivity of the C-15D rock frequency to Schiff base configuration (Ames et al., Biochemistry 1989, 28, 3681-3687). This work on retinals with chemically defined configuration and conformation provides a basis for further analysis of the geometry of these bonds in retinal-containing pigments.

  DOI：

  10.1021/ja00053a023
• 作为产物：
  描述：

  在 吡啶 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 [(3E,5E,7E)-3-[(E)-1-cyanoprop-1-en-2-yl]-6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-3,5,7-trienyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis and vibrational analysis of a locked 14-s-cis conformer of retinal.

  摘要：

  A 12-N-ethano retinal Schiff base is synthesized to study the vibrational properties of a C-14-C-15 s-cis conformer of retinal. The synthesis of the 12-N-ethano retinal Schiff base and seven of its isotopomers is described. Raman and FTIR spectra of this compound and its isotopic derivatives are analyzed and the normal mode assignments compared to MNDO normal coordinate calculations. The frequency of the C-14-C-15 stretch at 1096 cm-1 is approximately 100 cm-1 below typical values for s-trans conformers of retinal polyenes, supporting previous arguments that s-cis conformers will have characteristically low frequencies for the C-C stretch of the s-cis bond (Smith et al., Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 967-971). Deuteriation at the 15-position produces two modes at 950 and 1044 cm-1 that contain C-15D rock character. The elevated frequency (1044 cm-1) of the high-frequency component is a marker band for the C=N syn geometry and confirms an earlier analysis of the sensitivity of the C-15D rock frequency to Schiff base configuration (Ames et al., Biochemistry 1989, 28, 3681-3687). This work on retinals with chemically defined configuration and conformation provides a basis for further analysis of the geometry of these bonds in retinal-containing pigments.

  DOI：

  10.1021/ja00053a023