trans-4-(3′,4′-dimethoxyphenyl)but-3-ene | 76252-28-3

• 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: trans-4-(3′,4′-dimethoxyphenyl)but-3-ene
• 英文别名: (E)-4-(but-1-enyl)-1,2-dimethoxybenzene；(E)-1-(3,4-dimethoxyphenyl)-1-butene；(E)-1-(3,4-dimethoxyphenyl)but-1-ene；trans-(3,4-dimethoxyphenyl)but-1-ene；(E)-1-(3',4'-Dimethoxyphenyl)but-1-ene；4-[(E)-but-1-enyl]-1,2-dimethoxybenzene
• CAS: 76252-28-3
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: BONZIDALUXBFRW-AATRIKPKSA-N

物化性质

• 沸点：
  288.0±20.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)
• 保留指数：
  1612;1616

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-4-(3′,4′-dimethoxyphenyl)but-3-ene 、 N-甲基芸香碱 以 neat (no solvent) 为溶剂， 反应 16.0h， 以10%的产率得到(1RS,2RS,2aRS,10aSR)-2-(3,4-dimethoxyphenyl)-1-ethyl-4,10,10-trimethyl-1,2,2a,4,10,10a-hexahydro-3H-cyclobuta[4,5]pyrano[3,2-c]-quinolin-3-one
  参考文献：
  名称：

  Euodenine A: A Small-Molecule Agonist of Human TLR4

  摘要：

  A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-kappa B reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-alpha, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.

  DOI：

  10.1021/jm401321v
• 作为产物：
  描述：

  3',4'-二甲氧基苯丁酮 在 sodium tetrahydroborate 、 硫酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.0h， 生成 trans-4-(3′,4′-dimethoxyphenyl)but-3-ene
  参考文献：
  名称：

  Further characterization of the constituents of a thai medicinal plant, Zingiber cassumunar Roxb.

  摘要：

  从泰国药用植物姜黄（Zingiber cassumunar）的根茎中分离出了13种芳香化合物，这些化合物具有C6-C4、C6-C8-C6或C6-C10的碳骨架。其中8种化合物为新化合物，其结构通过化学和光谱方法被阐明为6、7、8、9、10、11、12和13。其结构通过13C-NMR光谱法得到了确认。

  DOI：

  10.1248/cpb.28.2948

文献信息

• An Effective System to Synthesize Hypolipidemic Active α-Asarone and Related Methoxylated (<i>E</i>)-Arylalkenes
  作者：Anuj Sharma、Bhupendra P. Joshi、Arun K. Sinha

  DOI：10.1246/bcsj.77.2231

  日期：2004.12

  Methoxylated (E)-arylalkenes (1a–1k) were prepared in two steps by an improved Grignard reaction comprising the reverse addition of alkylmagnesium bromide to benzaldehydes (2a–2k) in anhydrous ether and toluene into arylalkanols (3a–3k) in high yield, followed by dehydration with silica gel under microwave irradiation for 3–12 min, depending upon the substituents attached to the aromatic ring to afford hypolipidemic active α-asarone (1a) and related methoxylated (E)-arylalkenes (1b–1k).

  通过改进的Grignard反应，分两步制备了甲氧基化（E）-芳基烯烃（1a-1k）。该反应包括在无水乙醚和甲苯中反向加成烷基镁溴化物至苯甲醛（2a-2k），高产率地转化为芳基醇（3a-3k），随后在微波辐射下，根据芳香环上取代基的不同，利用硅胶进行脱水处理3-12分钟，得到具有降脂活性的α-细辛素（1a）及相关甲氧基化（E）-芳基烯烃（1b-1k）。
• Utilisation cosmétique d'une cassumunarine, d'un arylbutenoide et/ou d'un extrait botanique en contenant
  申请人：Chanel Parfums Beauté

  公开号：EP1870136A1

  公开（公告）日：2007-12-26

  La présente invention concerne un procédé cosmétique de soin de la peau, destiné à prévenir et/ou traiter au moins un signe cutané du vieillissement, comprenant l'application topique sur la peau d'une composition renfermant au moins un actif choisi parmi une cassumunarine, un arylbuténoïde et un extrait botanique en contenant, tel qu'un extrait de Zingiber cassumunar Roxb.

  本发明涉及一种旨在预防和/或治疗至少一种皮肤老化迹象的皮肤美容方法，包括在皮肤上局部涂抹一种组合物，该组合物含有至少一种活性成分，这些活性成分选自一种决明子苷、一种芳基丁烯酸和一种含有它们的植物提取物，例如决明子提取物。
• Ultrasound-assisted convenient synthesis of hypolipidemic active natural methoxylated (E)-arylalkenes and arylalkanones
  作者：Bhupendra P. Joshi、Anuj Sharma、Arun K. Sinha

  DOI：10.1016/j.tet.2005.01.071

  日期：2005.3

  An ultrasound-assisted convenient method was developed for the conversion of toxic methoxylated cis-isomer of arylalkenes into its hypolipidemic active trans-isomer. Treatment of cis-isomer or mixture of all three isomers (1a-1j) with ammonium formate and 10% Pd/C gave arylalkanes (2a-2j), which upon oxidation with DDQ in anhydrous dioxane containing a little amount of silica gel, provided (E)-arylalkenes (3a-3g) in 42-72% yield depending upon the substituents attached at the aryl ring. The same method, upon addition of a few drops of water, provided hypolipidemic active arylalkanones (3h-3j) in 59-65% yield. (c) 2005 Elsevier Ltd. All rights reserved.
• One-pot synthesis of trans-β-alkylstyrenes
  作者：Ju-Tsung Liu、Ching-Fa Yao

  DOI：10.1016/s0040-4039(01)01185-6

  日期：2001.8

  One-pot synthesis of (E)-alkenes 5 from the reactions of aldehyde 1 and nitromethane 2 in the acetic acid solution and then with triethylborane 4 in the biphase of diethyl ether and aqueous Solution ill the presence of oxygen in air was reported. Various (E)-alkenes 7 could also be prepared when different kinds of secondary or tertiary alkyl iodides 6 were used under similar conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Domino synthesis of indenols and alkyl-indene ethers under modified Vilsmeier conditions
  作者：Parvinder Pal Singh、P. Bhaskar Reddy、Sanghapal D. Sawant、S. Koul、S.C. Taneja、H.M. Sampath Kumar

  DOI：10.1016/j.tetlet.2006.07.126

  日期：2006.10

  Indenols are produced in high yields through domino reactions, when electron-rich trans-stilbenes and other trans arylalkyl olefins were subjected to Vilsmeier formylation in the presence of excess POCl3 in a one-pot procedure. The method is even suitable for converting aryl-alkyl carbinols (precursors for olefins) directly into indenols. The corresponding indene ethers could be prepared in high yields directly when less reactive alpha,beta-unsaturated aldehydes were subjected to cyclization in alcoholic HCl. (c) 2006 Elsevier Ltd. All rights reserved.