(2E,4E)-3-methyl-5-phenylpenta-2,4-dienal | 53701-48-7

• 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: (2E,4E)-3-methyl-5-phenylpenta-2,4-dienal
• CAS: 53701-48-7
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: MSUVMPDTEDUDAY-MFDVASPDSA-N

物化性质

• 沸点：
  312.2±21.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 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-phenylpenta-2,4-dienal 在 盐酸 、 potassium tert-butylate 、 水 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 2.25h， 生成 (2E,4E,6E,8E)-3,7-二甲基-9-苯基壬-2,4,6,8-四烯醛
  参考文献：
  名称：

  Prenylation Reaction Performed with Catalytically Generated Potassium Prenal Dienolate

  摘要：

  本文介绍了一种新的预炔化方法，该方法基于催化生成的预炔二烯酸钾与δ、δ²-不饱和醛的反应。该反应通过δ-1,2-加成具有高度的区域选择性，并提供了获得视黄醛的有效途径。

  DOI：

  10.1055/s-1998-1955
• 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， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 4.66h， 生成 (2E,4E)-3-methyl-5-phenylpenta-2,4-dienal
  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

• 4-(t-butylthio)-3-buten-2-one. Synthon for α,β- and α,β,γ,δ-unsaturated aldehyde synthesis
  作者：Shuzo Akiyama、Shin'ichi Nakatsuji、Toshihiko Hamamura、Motohiro Kataoka、Masazumi Nakagawa

  DOI：10.1016/s0040-4039(01)86422-4

  日期：1979.1

  A convenient synthesis of α,β- and α,β,γ,δ-unsaturated aldehydes using readily accessible 4-(t-butylthio)-3-buten-2-one as synthon was described.

  描述了使用容易获得的4-（叔丁硫基）-3-丁烯-2-酮作为合成子方便地合成α，β-和α，β，γ，δ-不饱和醛的方法。
• A New Method for the Preparation of δ-Alkoxy-α,β-unsaturated Aldehydes and Polyenals
  作者：Akihiko Ishida、Teruaki Mukaiyama

  DOI：10.1246/bcsj.50.1161

  日期：1977.5

  TiCl4 and also in the coexistence of TiCl4 and Ti(OiPr)4 to give δ-alkoxy-α,β-unsaturated aldehydes (3–5) in good yields. In the presence of 1,8-diazabicyclo[5.4.0] undec-7-ene or 1,5-diazabicyclo[4.3.0]non-5-ene and molecular sieves 3A or 4A, the elimination reaction of δ-alkoxyl group of α,β-unsaturated aldehydes (3–5) proceeds smoothly to afford the corresponding polyenals in good yields.

  二烯氧基硅烷 (2) 在 TiCl4 存在下以及 TiCl4 和 Ti(OiPr)4 共存下与缩醛反应，以良好的产率得到 δ-烷氧基-α,β-不饱和醛 (3-5)。在1,8-二氮杂双环[5.4.0]十一碳-7-烯或1,5-二氮杂双环[4.3.0]非5-烯和分子筛3A或4A存在下，δ-烷氧基的消除反应α,β-不饱和醛 (3-5) 的合成顺利进行，以良好的收率提供相应的多烯醛。
• 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
• Histone deacetylase inhibitors
  申请人：CircaGen Pharmaceutical, a Delaware corporation

  公开号：US20020143037A1

  公开（公告）日：2002-10-03

  Histone deacetylase is a metallo-enzyme with zinc at the active site. Compounds having a zinc-binding moiety, such as, for example, a carboxylic acid group, can inhibit histone deacetylase. Histone deacetylase inhibition can repress gene expression, including expression of genes related to tumor suppression. Accordingly, inhibition of histone deacetylase can provide an alternate route for treating cancer, hematological disorders, e.g., hemoglobinopathies, and genetic related metabolic disorders, e.g., cystic fibrosis and adrenoleukodystrophy.

  组蛋白去乙酰化酶是一种在活性位点含锌的金属酶。具有锌结合基团的化合物，例如，羧酸基团，可以抑制组蛋白去乙酰化酶。组蛋白去乙酰化酶的抑制可以抑制基因表达，包括与肿瘤抑制相关的基因的表达。因此，抑制组蛋白去乙酰化酶可以提供治疗癌症、血液学疾病（例如血红蛋白病）以及遗传相关代谢性疾病（例如囊性纤维化和肾上腺白质脑病）的另一途径。
• Stereocontrolled Synthesis of (<i>E,Z</i>)-Dienals <i>via</i> Tandem Rh(I)-Catalyzed Rearrangement of Propargyl Vinyl Ethers
  作者：Dinesh V. Vidhani、Marie E. Krafft、Igor V. Alabugin

  DOI：10.1021/ol4019985

  日期：2013.9.6

  A novel Rh(I)-catalyzed approach to functionalized (E,Z) dienals 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 protodemetalation

  通过串联转化开发了新颖的Rh（I）催化的官能化（E，Z）二烯醛的方法，其中立体选择性氢转移遵循炔丙基克莱森重排。第一个双键的Z-立体化学表明一个六元环状中间体的参与，而第二个双键的E-立体化学则来自随后的原金属脱金属步骤，产生一个（E，Z）-二烯。