3-(1-azulenyl)propenal | 94053-50-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3-(1-azulenyl)propenal
• 英文别名: 3-(azulen-1-yl)acrylaldehyde；(E)-3-(azulen-1-yl)acrylaldehyde；3-(1-azulenyl)-2-propenal；(E)-3-azulen-1-ylprop-2-enal
• CAS: 94053-50-6
• 化学式: C₁₃H₁₀O
• 分子量: 182.222
• InChiKey: LIEAZMDVOGYATG-GQCTYLIASA-N

物化性质

• 沸点：
  360.2±11.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-(1-azulenyl)propenal 在 titanium(III) chloride 、 lithium 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 以33%的产率得到1,6-Bis(1-azulenyl)-1,3,5-hexatrien
  参考文献：
  名称：

  Huenig, Siegfried; Ort, Burkhard, Liebigs Annalen der Chemie, 1984, # 12, p. 1905 - 1935

  摘要：

  DOI：
• 作为产物：
  描述：

  2-丙烯腈,3-(1-薁基)-,(2E)- 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到3-(1-azulenyl)propenal
  参考文献：
  名称：

  Azulenic retinoids: novel nonbenzenoid aromatic retinoids with anticancer activity

  摘要：

  Several novel azulene-containing retinoids were prepared and evaluated for their ability to suppress carcinogen-induced neoplastic transformation and to concomitantly up-regulate gap junctional communication in the in vitro mouse fibroblast C3H/10T1/2 cell bioassay. The azulenic retinoids were divided into two groups: compounds 1-6 were modeled after retinoic acid with flexible polyenic side chain whereas retinoids 7-13 featured a benzoic acid moiety analogous to the prototypic retinobenzoate (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid (TTNPB). Within this latter group the side chains for compounds 7, 10, and 11 were attached at the 1-, 2-, and 8-positions of the azulenic terminus, respectively. Biological activities were determined for all the new compounds. Two of these novel retinoids, azulenic retinobenzoic acid derivatives 7 and 11, were completely effective inhibitors of transformation at 10(-6) M. The most active azulenic retinoids also enhanced gap junctional communication in untransformed cells; this was associated with up-regulated expression of connexin 43, a structural protein of the gap junction. Two fluorinated analogs were also tested. The azulenic fluoro acid 5 was found to be more potent than the trifluoromethyl analog 6. Azulenic analogs with hydroxyl or carboxaldehyde side chain functional groups were ineffective transformation inhibitors. In general, azulenic retinobenzoic acid analogs structurally akin to TTNPB were more effective than flexible side chain analogs related to retinoic acid.

  DOI：

  10.1021/jm00073a013

文献信息

• Vinylazulenes chromophores: Synthesis and characterization
  作者：Liviu Birzan、Mihaela Cristea、Constantin C. Draghici、Victorita Tecuceanu、Maria Maganu、Anamaria Hanganu、Alexandru C. Razus、George Octavian Buica、Eleonora Mihaela Ungureanu

  DOI：10.1016/j.dyepig.2016.02.033

  日期：2016.8

  Several vinylazulenes containing heterocyclic units were prepared using Knoevenagel condensation. The condensation took place between electron rich 1-azulenecarbaldehyde derivatives and their vinylogues with heterocycles. The catalysts were chosen in order to catalyze the reaction without giving side reactions, such as heterocycle decomposition or formylazulene decarbonylation. Several NMR signals

  使用Knoevenagel缩合反应制备了几种含杂环单元的乙烯基azulenes。富电子的1-氮杂苯甲醛衍生物与它们的带有杂环的乙烯基之间发生缩合。选择催化剂是为了催化反应而不产生副反应，例如杂环分解或甲酰祖烯脱羰基。简要讨论了几个NMR信号。有色物质的光学性质被证明是其结构的函数。两种化合物证明了生色团的pH依赖性。以及它们的活性溶剂变色。从氧化还原电势评估其电化学性质，并将其与结构相关。
• Azulenic retinoid compounds, compositions and methods
  申请人：University of Hawaii

  公开号：US05235076A1

  公开（公告）日：1993-08-10

  Novel azulenic retinoid compounds and therapeutic compositions are disclosed, along with method for their production and use as anti-cancer and cancer-prevention agents. The compositions of the present invention will also find use in treating dermatological disorders such as acne and psoriasis, as well as dermatologically-related conditions such as repair and effacement of wrinkles.

  本发明揭示了新型蓝花烯类视黄醇化合物和治疗组合物，以及它们的生产方法和作为抗癌和预防癌症剂的用途。本发明的组合物还可用于治疗皮肤疾病，如痤疮和牛皮癣，以及与皮肤相关的条件，如皱纹修复和消除。
• Photophysical, electrochemical, and photoelectrochemical properties of new azulene-based dye molecules
  作者：Xue-Hua Zhang、Chao Li、Wei-Bo Wang、Xue-Xin Cheng、Xue-Song Wang、Bao-Wen Zhang

  DOI：10.1039/b613703b

  日期：——

  Four new azulene-based dye molecules, 3-(azulen-1-yl)-2-cyanoacrylic acid (Azu-1), 3-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanoacrylic acid (Guai-1), 5-(azulen-1-yl)-2-cyanopenta-2,4-dienoic acid (Azu-2), and 5-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanopenta-2,4-dienoic acid (Guai-2), were synthesized and their photoelectrochemical properties were studied in dye-sensitized solar cells (DSSCs). All of them exhibit, in the visible region, a strong absorption band coming from the S0–S2 transition and a very weak band coming from the S0–S1 transition, and the transition assignments are supported by theoretical calculations using time-dependent density functional theory (TD-DFT) at the B3LYP/6–31G* level. In sensitization of nanocrystalline TiO2 electrodes, reducing their adsorption amount on the TiO2 surface (by co-adsorption with deoxycholic acid) mitigates dye aggregation and improves their photoelectric conversion efficiency greatly. Also, extending the conjugated side chain (Azu-2vs.Azu-1 or Guai-2vs.Guai-1) not only shifts their photoelectric response to longer wavelengths and therefore enhances the short-circuit photocurrent, but also increases the open-circuit photovoltage significantly. Moreover, it was found that the electron injection efficiencies varied remarkably with excitation wavelength, suggesting direct electron injection from the S2 state of these dye molecules.

  四种新型甘菊环染料分子，3-(azulen-1-yl)-2-氰基丙烯酸 (Azu-1)、3-(7-异丙基-1,4-二甲基甘菊环-3-基)-2-氰基丙烯酸(Guai-1)、5-(azulen-1-yl)-2-氰基五-2,4-二烯酸 (Azu-2) 和 5-(7-异丙基-1,4-二甲基azulen-3-yl)合成了-2-氰基戊酸-2,4-二烯酸（Guai-2），并在染料敏化太阳能电池（DSSC）中研究了其光电化学性质。它们在可见光区域都表现出来自 S0-S2 跃迁的强吸收带和来自 S0-S1 跃迁的非常弱的吸收带，并且跃迁分配得到了使用瞬态密度泛函理论的理论计算的支持(TD-DFT) 在 B3LYP/6–31G* 水平。在纳米晶TiO2电极的敏化中，减少其在TiO2表面的吸附量（通过与脱氧胆酸共吸附）可以减轻染料聚集并大大提高其光电转换效率。此外，延长共轭侧链（Azu-2vs.Azu-1或Guai-2vs.Guai-1）不仅将其光电响应转移到更长的波长，从而增强短路光电流，而且还增加了开路光电压显著地。此外，还发现电子注入效率随激发波长变化显着，表明电子从这些染料分子的 S2 态直接注入。
• EP0588915A4
  申请人：——

  公开号：EP0588915A4

  公开（公告）日：1995-05-31
• AZULENIC RETINOID COMPOUNDS, COMPOSITIONS AND METHODS
  申请人：UNIVERSITY OF HAWAII

  公开号：EP0588915A1

  公开（公告）日：1994-03-30