(2E,4E)-3-methyl-5-(2-naphthyl)penta-2,4-dienal | 102672-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2E,4E)-3-methyl-5-(2-naphthyl)penta-2,4-dienal
• 英文别名: 3-methyl-5-(naphthalen-3-yl)penta-2,4-dienal；(2E,4E)-3-methyl-5-naphthalen-2-ylpenta-2,4-dienal
• CAS: 102672-97-9
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: XJEMPGQIYLAFDW-FCXQYMQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (2E,4E)-3-methyl-5-(2-naphthyl)penta-2,4-dienal 在 sodium tetrahydroborate 、 二氢吡啶 、 C₇₇H₁₁₇N₁₄O₁₃Pol*C₂HF₃O₂ 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 36.33h， 生成 3-methyl-5-(2-naphthyl)pentan-1-ol
  参考文献：
  名称：

  肽催化的α，β，γ，δ不饱和醛的区域和对映选择性还原

  摘要：

  在标题反应中使用了树脂负载的肽催化剂（参见方案中的方框）。肽催化剂克服了固有的区域选择性，从而在1,4还原之前促进了1,6选择性反应。当使用起始醛的几何异构体的混合物时，也实现了高立体收敛性。Ach = 1-氨基-1-环己烷羧酸

  DOI：

  10.1002/anie.201305004
• 作为产物：
  描述：

  3-甲基-4-膦酰丁烯酸三乙酯 在 N,N-二甲基丙烯基脲 、 manganese(IV) oxide 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 hexanes 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 (2E,4E)-3-methyl-5-(2-naphthyl)penta-2,4-dienal
  参考文献：
  名称：

  Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

  摘要：

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.008

文献信息

• Peptide-Catalyzed Regio- and Enantioselective Reduction of α,β,γ,δ-Unsaturated Aldehydes
  作者：Kengo Akagawa、Jun Sen、Kazuaki Kudo

  DOI：10.1002/anie.201305004

  日期：2013.10.25

  in the title reaction. The inherent regioselectivity was overcome by the peptide catalyst to promote the 1,6‐selective reaction prior to 1,4‐reduction. High stereoconvergence was also achieved when using a mixture of geometric isomers of the starting aldehydes. Ach=1‐amino‐1‐cyclohexanecarboxylic acid.

  在标题反应中使用了树脂负载的肽催化剂（参见方案中的方框）。肽催化剂克服了固有的区域选择性，从而在1,4还原之前促进了1,6选择性反应。当使用起始醛的几何异构体的混合物时，也实现了高立体收敛性。Ach = 1-氨基-1-环己烷羧酸
• Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part
  作者：George E. Magoulas、Stavros E. Bariamis、Constantinos M. Athanassopoulos、Anastasios Haskopoulos、Petros G. Dedes、Marios G. Krokidis、Nikos K. Karamanos、Dimitris Kletsas、Dionissios Papaioannou、George Maroulis

  DOI：10.1016/j.ejmech.2010.12.008

  日期：2011.2

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.