2-丙烯腈,3-(1-薁基)-,(2E)- | 146431-94-9

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 2-丙烯腈,3-(1-薁基)-,(2E)-
• 英文名称: (E)-3-(azulen-1-yl)-acrylonitrile
• 英文别名: 3-(1-azulenyl)propenenitrile；3-(1-azulenyl)-2-propenenitrile；(E)-3-azulen-1-ylprop-2-enenitrile
• CAS: 146431-94-9
• 化学式: C₁₃H₉N
• 分子量: 179.221
• InChiKey: GWQWPBYUOXIIGC-GQCTYLIASA-N

物化性质

• 熔点：
  123-125 °C
• 沸点：
  363.6±11.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  氰甲基磷酸二乙酯 、 薁-1-甲醛 在 lithium diisopropyl amide 作用下， 生成 2-丙烯腈,3-(1-薁基)-,(2E)-
  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

• 2-Substituted (Azulen-1-yl)ethenes
  作者：Alexandru C. Razus、Carmen Nitu、Victorita Tecuceanu、Valentin Cimpeanu

  DOI：10.1002/ejoc.200300346

  日期：2003.12

  An easy and efficient solvent-free synthesis of 1-(azulen-1-yl)-2-aryl- and heteroarylethenes is described. The reaction was performed simply by melting solid mixtures of azulenic Schiff bases and arylacetic acids, the crude products being purified by column chromatography. Limitations of the method were established by study of a large range of aryl and heteroarylacetic acids and also by examination

  描述了一种简单有效的无溶剂合成 1-(azulen-1-yl)-2-aryl-和heteroarylethenes。该反应简单地通过熔化蕈基席夫碱和芳基乙酸的固体混合物来进行，粗产物通过柱色谱法纯化。该方法的局限性是通过研究大范围的芳基和杂芳基乙酸以及检查各种蕈烯席夫碱来确定的。对于其他活性亚甲基化合物，如丙二酸及其衍生物或 1,3-二酮，也观察到了相同的反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• 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。
• A comprehensive investigation of the interrelationships between spectroscopy and photochemistry and substituents of some azulenic derivatives
  作者：Hongru Li、Fang Gao、Alfred E. Asato、Robert S.H. Liu

  DOI：10.1016/j.saa.2007.02.024

  日期：2008.1

  azulenes, have been synthesized to survey their photophysics and photochemistry. These azulenes display S(2)-->S(0) emission, but with several differences. This is the most remarkable characteristic of the effect of orbital control on color and excited state properties of the azulenic compounds. This paper emphasizes how emission spectra and photochemistry of azulenic compounds are influenced by their

  已经合成了几种含氮烯的染料，包括六种氮烯烃，两种氮烯醛和两种烯属氮烯，以研究其光物理性质和光化学性质。这些天青石显示出S（2）-> S（0）发射，但有一些区别。这是轨道控制对天青石化合物的颜色和激发态性质的影响的最显着特征。本文强调了天青石化合物的发射光谱和光化学如何受到其化学结构和溶剂的影响。z烃的发射光谱表明，它们的激发态性质可以通过其分子结构和大小来控制。通过发射和（1）H NMR光谱证实，在强酸如三氟乙酸（TFA）中，a并单醛被质子化。在照射过程中观察到苯乙烯基la烯的光化学。Azulenic化合物具有热稳定性和颜色可调性，因此，它们是非线性光学材料的良好候选者。基于其独特的光化学和光物理特性，可以构建新颖的天青石染料以用于不同用途。
• 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