2-methoxy-4-nonylbenzaldehyde | 153686-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methoxy-4-nonylbenzaldehyde
• CAS: 153686-17-0
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: ZRYYTLOYVGWQTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-methoxy-4-nonylbenzaldehyde 在 乙醇 、 三氟化硼乙醚 、 三溴化硼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 23.5h， 生成 meso-tetrakis(2-hydroxy-4-nonylphenyl)porphyrin
  参考文献：
  名称：

  Kinetic and Thermodynamic Analysis of Induced-Fit Molecular Recognition between Tetraarylporphyrin and Ubiquinone Analogues

  摘要：

  meso-Tetrakis(2-hydroxy-4-nonylphenyl)porphyrin (1), which was prepared as a host molecule for ubiquinone analogues, comprises four atropisomers, alpha alpha alpha alpha, alpha alpha alpha beta, alpha alpha beta beta, and alpha beta alpha beta, in a statistical ratio of 1:4:2:1, respectively. The atropisomerization is due to internal rotation about the C(aryl)-C(porphyrin) bonds and is observed even at room temperature, A rate constant for the rotation was determined (k = 1.73 x 10(-5) s(-1) in CHCl3 at 25 degrees C). UV/visible spectrophotometric titration of tetramethoxy-p-benzoquinone (3) against 1(alpha alpha alpha alpha) or 1(alpha alpha alpha beta) in CHCl3 at 25 degrees C showed 1:1 complexation with association constants of (9.4 +/- 0.1) x 10(3) and (3.5 +/- 0.1) x 10(2) M-1, respectively. Upon addition of 3 to a solution of 1 in CDCl3, the proportion of 1(alpha alpha alpha alpha) in the atropisomeric mixture increased and that of the other three isomers decreased over 500 h. At equilibrium the proportion of 1(alpha alpha alpha alpha) reached 78% in the presence of 3 (3 equiv); this showed that atropisomerization is induced by complexation with 3, An atropisomeric shift to 1(alpha alpha alpha alpha) was also observed upon addition of 2,3-dimethoxy-p-benzoquinone (4); however, the proportion of 1 alpha alpha alpha alpha was only 30% at equilibrium, since the difference in binding affinities between 1(alpha alpha alpha alpha)-4 and 1(alpha alpha alpha beta)-4 complexes is relatively small compared with that between 1(alpha alpha alpha alpha)-3 and 1(alpha alpha alpha beta)-3 complexes. Nickel and zinc porphyrins. 1.Ni and 1.Zn, also showed induced-fit interaction with 3. The atropisomeric shift to 1(alpha alpha alpha alpha).Ni upon addition of 3 was completed within Ih. whereas guest-induced atropisomerization in 1.Zn was much slower than in free base 1. The observed changes in the relative amounts of the four atropisomers are identical with the simulated changes calculated from multiple equilibrium systems by use of kinetic and thermodynamic parameters. This system is a suitable model for induced-fit molecular recognition in flexible enzymes.

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1266::aid-chem1266>3.0.co;2-t
• 作为产物：
  描述：

  nonylmagnesium bromide 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 四氯化钛 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-methoxy-4-nonylbenzaldehyde
  参考文献：
  名称：

  Kinetic and Thermodynamic Analysis of Induced-Fit Molecular Recognition between Tetraarylporphyrin and Ubiquinone Analogues

  摘要：

  meso-Tetrakis(2-hydroxy-4-nonylphenyl)porphyrin (1), which was prepared as a host molecule for ubiquinone analogues, comprises four atropisomers, alpha alpha alpha alpha, alpha alpha alpha beta, alpha alpha beta beta, and alpha beta alpha beta, in a statistical ratio of 1:4:2:1, respectively. The atropisomerization is due to internal rotation about the C(aryl)-C(porphyrin) bonds and is observed even at room temperature, A rate constant for the rotation was determined (k = 1.73 x 10(-5) s(-1) in CHCl3 at 25 degrees C). UV/visible spectrophotometric titration of tetramethoxy-p-benzoquinone (3) against 1(alpha alpha alpha alpha) or 1(alpha alpha alpha beta) in CHCl3 at 25 degrees C showed 1:1 complexation with association constants of (9.4 +/- 0.1) x 10(3) and (3.5 +/- 0.1) x 10(2) M-1, respectively. Upon addition of 3 to a solution of 1 in CDCl3, the proportion of 1(alpha alpha alpha alpha) in the atropisomeric mixture increased and that of the other three isomers decreased over 500 h. At equilibrium the proportion of 1(alpha alpha alpha alpha) reached 78% in the presence of 3 (3 equiv); this showed that atropisomerization is induced by complexation with 3, An atropisomeric shift to 1(alpha alpha alpha alpha) was also observed upon addition of 2,3-dimethoxy-p-benzoquinone (4); however, the proportion of 1 alpha alpha alpha alpha was only 30% at equilibrium, since the difference in binding affinities between 1(alpha alpha alpha alpha)-4 and 1(alpha alpha alpha beta)-4 complexes is relatively small compared with that between 1(alpha alpha alpha alpha)-3 and 1(alpha alpha alpha beta)-3 complexes. Nickel and zinc porphyrins. 1.Ni and 1.Zn, also showed induced-fit interaction with 3. The atropisomeric shift to 1(alpha alpha alpha alpha).Ni upon addition of 3 was completed within Ih. whereas guest-induced atropisomerization in 1.Zn was much slower than in free base 1. The observed changes in the relative amounts of the four atropisomers are identical with the simulated changes calculated from multiple equilibrium systems by use of kinetic and thermodynamic parameters. This system is a suitable model for induced-fit molecular recognition in flexible enzymes.

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1266::aid-chem1266>3.0.co;2-t

文献信息

• Synthesis of Novel Structurally Simplified Estrogen Analogues with Electron-Donating Groups in Ring A
  作者：Lutz Tietze、Carsten Vock、Ilga Krimmelbein、Linda Nacke

  DOI：10.1055/s-0029-1216810

  日期：2009.6

  A library of 25 novel estrogen analogues were prepared in five to eight steps from mostly commercially available substituted anisoles via bromination, formylation, Corey-Fuchs reaction, elimination, and Sonogashira reaction.

  合成了一系列25种新型雌激素类似物，这些化合物通过五个至八个步骤，主要以市售的取代茴香醚为原料，经过溴化、甲醛化、Corey-Fuchs反应、消除反应及Sonogashira反应制备得到。
• Hayashi, Takashi; Asai, Tomobito; Hokazono, Hirohisa, Journal of the American Chemical Society, 1993, vol. 115, # 25, p. 12210 - 12211
  作者：Hayashi, Takashi、Asai, Tomobito、Hokazono, Hirohisa、Ogoshi, Hisanobu

  DOI：——

  日期：——