(2E,4E)-5-(4'-methoxyphenyl)-3-methyl-2,4-pentadienal | 77144-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,4E)-5-(4'-methoxyphenyl)-3-methyl-2,4-pentadienal
• 英文别名: (2E,4E)-5-(4-methoxyphenyl)-3-methylpenta-2,4-dienal；5-(4-methoxyphenyl)-3-methyl-2E,4E-pentadienal；5-(4-methoxyphenyl)-3-methyl-3E,4E-pentadienal；5-(4-methoxyphenyl)-3-methyl-2,4-pentadienal
• CAS: 77144-25-3
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: SAGKLPPTOAIAKI-QRSDNQECSA-N

物化性质

• 熔点：
  78 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  366.3±25.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(4'-methoxyphenyl)-3-methyl-2,4-pentadienal 在 sodium hydroxide 、 硫酸 作用下， 反应 49.75h， 生成 ethyl 9-(4-methoxyphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate
  参考文献：
  名称：

  Makin, S. M.; Mikerin, I. E.; Shavrygina, O. A., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 2, p. 313 - 318

  摘要：

  DOI：
• 作为产物：
  描述：

  triethyl 3-methyl-4-phosphonocrotonate 在 N,N-二甲基丙烯基脲 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 生成 (2E,4E)-5-(4'-methoxyphenyl)-3-methyl-2,4-pentadienal
  参考文献：
  名称：

  Photocurrents of solar cells sensitized by aggregate-forming polyenes: Enhancement due to suppression of singlet–triplet annihilation by lowering of dye concentration or light intensity

  摘要：

  Titania-based Gratzel-type solar cells were fabricated by the use of polyene dyes with various transition dipole moments. in the dye having the largest transition dipole among the samples, an aggregate was readily formed through dispersive interaction, and the photocurrent was increased when the dye concentration or the light intensity was lowered. This observation was ascribed to the suppression of the singlet-triplet annihilation reaction. In the dye having the smallest transition dipole, there was no sign of aggregate formation, and the photocurrent was decreased when the dye concentration or the light intensity was lowered. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cplett.2006.01.003

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
• STERO CONTROLLED SYNTHESIS OF (E,Z)-DIENALS VIA TANDEM RH(I) CATALYZED PROPARGYL CLAISEN REARRANGEMENT
  申请人：The Florida State University Research Foundation, Inc.

  公开号：US20150361019A1

  公开（公告）日：2015-12-17

  A novel Rh(I)-catalyzed approach to synthesizing functionalized (E,Z) dienal compounds has been developed via tandem transformation where a stereoselective hydrogen transfer follows a propargyl Claisen rearrangement. Z-Stereochemistry of the first double bond suggests the involvement of a six-membered cyclic intermediate whereas the E-stereochemistry of the second double bond stems from the subsequent protodemetallation step giving an (E,Z)-dienal. The reaction may be represented by the following sequence.

  已经开发出一种新颖的Rh(I)催化方法，用于合成功能化的(E,Z)二烯醛化合物，通过串联转化，其中立体选择性的氢转移跟随着一个炔丙基Claisen重排。第一个双键的Z-立体化学表明涉及一个六元环中间体，而第二个双键的E-立体化学源自随后的脱金属化步骤，形成一个(E,Z)-二烯醛。该反应可以用以下序列表示。
• One-Step Vilsmeier Route to Some 5-Aryl-3-methyl-2(<i>E</i>),4(<i>E</i>)-pentadienals and their Oxidation to Pentadienoic Acids
  作者：M. Parameswara Reddy、G. S. Krishna Rao

  DOI：10.1055/s-1980-29219

  日期：——
• Makin, S. M.; Mikerin, I. E.; Dobretsova, E. K., Russian Journal of Organic Chemistry, 1993, vol. 29, # 4, p. 572 - 575
  作者：Makin, S. M.、Mikerin, I. E.、Dobretsova, E. K.、Shavrygina, O. A.

  DOI：——

  日期：——
• Makin, S. M.; Mikerin, I. E.; Shavrygina, O. A., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 4.2, p. 710 - 715
  作者：Makin, S. M.、Mikerin, I. E.、Shavrygina, O. A.、Lanina, T. I.

  DOI：——

  日期：——