4-tert-butyldimethylsiloxycinnamic acid | 848251-51-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-tert-butyldimethylsiloxycinnamic acid
• 英文别名: 4-tert-butyldimethylsilyloxicinnamic acid；3-[4-[Tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-enoic acid
• CAS: 848251-51-4
• 化学式: C₁₅H₂₂O₃Si
• 分子量: 278.423
• InChiKey: MYGJZPUJVGFYDK-UHFFFAOYSA-N

物化性质

• 熔点：
  127-129 °C
• 沸点：
  352.8±25.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-tert-butyldimethylsiloxycinnamic acid 在 Oxone 、 三乙胺氢溴酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-(4-(2-bromovinyl)phenoxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Triazole-curcuminoids: A new class of derivatives for ‘tuning’ curcumin bioactivities?

  摘要：

  Curcumin is a unique blend of pharmacophores responsible for the pleiotropy of this natural pigment. In the present study we have replaced the 1,3-dicarbonyl moiety with a 1,2,3-triazole ring to furnish a new class of triazole-curcuminoids as a possible strategy to generate new compounds with different potency and selectivity compared to curcumin. We obtained a proof-of-principle library of 28 compounds tested for their cytotoxicity (SY-SY5Y and HeLa cells) and for their ability to inhibit NF-kappa B. Furthermore, we also generated 1,3-dicarbonyl curcuminoids of selected click compounds. Triazole-curcuminoids lost their ability to be Michael's acceptors, yet maintained some of the features of the parent compounds and disclosed new ones. In particular, we found that some compounds were able to inhibit NF-kappa B without showing cytotoxicity, while others, unlike curcumin, activated NF-kappa B signalling. This validates the hypothesis that click libraries can be used to investigate the biological activities of curcumin as well as generate analogs with selected features. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.044
• 作为产物：
  描述：

  4-香豆酸 、 叔丁基二甲基氯硅烷 在 咪唑 、 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 4-tert-butyldimethylsiloxycinnamic acid
  参考文献：
  名称：

  中和新生成的齐墩果烯衍生物的半合成和结构-活性关系

  摘要：

  从（3 S，4 R）-23,28-Dihydroxyolean-12-en-3-yl（2 E）-3-（3,4-dihydroxyphenyl）丙烯酸酯（1 a）中分离出具有显着神经形成活性的传统中草药（Desmodium sambuense）植物。为了确定结构并评估生物活性，我们从市售齐墩果酸中半合成了1 a。小说系列1a然后设计并合成衍生物，以进行结构-活性关系（SAR）研究。所有合成衍生物均通过光谱数据分析进行表征，并在PC12细胞测定中评估了它们的神经生成活性。SAR结果表明，苯环和三萜烯部分上羟基的数量和位置，以及将苯环与三萜烯连接的（饱和或不饱和）烷基链的长度严重影响了神经形成活性。在所有测试的化合物中，发现了1 e [（3 S，4 R）-23,28-dihydroxyolean-12-en-3-yl（2 E）-3-（3,4,5-三羟基苯基）丙烯酸酯]最有效，可在1μm处引起明显的神经突生长。

  DOI：

  10.1002/cmdc.201800352

文献信息

• Two novel innovanoside dimers from Daphne aurantiaca and a concise total synthesis of diinnovanoside A
  作者：Shuang Liang、Shan-Xiang Liu、Hui-Zi Jin、Lei Shan、Shi-Chong Yu、Yun-Heng Shen、Hui-Liang Li、Qiu-Ye Wu、Qing-Yan Sun、Wei-Dong Zhang

  DOI：10.1039/c3cc41811a

  日期：——

  Chemical examination of the methanolic extract from the stem bark of Daphne aurantiaca led to the isolation of two innovanoside dimers (1 and 2) with an unusual four-membered cyclobutane ring, together with the isoinnovanoside 3. Their chemical structures and configurations were elucidated by extensive spectral analysis and synthesis.

  化学检测Daphne aurantiaca茎皮中的甲醇提取物导致分离出两个具有不寻常的四元环丁烷环的新诺苷二聚体（1和2）以及异新诺苷3。光谱分析和合成。
• Color regulation and stabilization of chromophore by Cys69 in photoactive yellow protein active center
  作者：Kentaro Okamoto、Norio Hamada、Taka-aki Okamura、Norikazu Ueyama、Hitoshi Yamamoto

  DOI：10.1039/b905835d

  日期：——

  Model compounds of PYP chromophore were synthesized and characterized to investigate the role of the Cys69 residue in the active center, which has the intramolecular NH⋯OC hydrogen bond to the conjugated carbonyl oxygen and thioester linkage of the chromophore. The results of UV-vis and 13C NMR spectroscopy of the model compounds indicated that they delocalized the negative charge of the chromophore and increased the contribution of the quinoid-like resonance structure in the phenolate anion state. Thus, the Cys69 residue plays an important role in the regulation of the color and the stabilization of the chromophore anion in the active center.

  合成并表征了PYP色素的模型化合物，以研究Cys69残基在活性中心中的作用，该残基与共轭羰基氧和色素硫酯键形成分子内NH⋯OC氢键。模型化合物的UV-vis和13C NMR光谱结果表明，它们使色素的负电荷发生离域，并增强了酚酸阴离子状态中类醌共振结构的贡献。因此，Cys69残基在活性中心中对色彩的调节和色素阴离子的稳定性起着重要作用。
• 化合物、液晶组合物、液晶显示元件、液晶显示器
  申请人：石家庄诚志永华显示材料有限公司

  公开号：CN112812012B

  公开（公告）日：2023-08-29

  本发明涉及下述的式I所示的化合物、液晶组合物及液晶显示器。本发明的化合物在液晶组合物中能够作为自组装光配向剂(SAPA)，通过光配向具有正或负介电各向异性的液晶组合物能够制造具有沿面配向的液晶(LC)显示器件。本发明的式I所示化合物经聚合能够得到稳定性好的光控取向膜，能够起到配向层的绝缘与对液晶分子水平配向的作用，能够避免配向层制程，使液晶显示元件或液晶显示器的制程得到简化，提高生产效率。
• Palladium(II) Acetate as Catalyst in Transvinylation Reactions of Hydroxycinnamic Acid and Its Derivatives
  作者：L.O. Kadidae、A. Usami、M. Honda

  DOI：10.14233/ajchem.2018.21033

  日期：——

  The study on application of palladium(II) acetate as catalyst in transvinylation reactions of hydroxycinnamic acids has been done. This study was intended to assess the capability of palladium(II) acetate as a safer replacement for mercuric(II) catalysts in transvinylation reactions of hydroxycinnamic acids and its derivatives. Optimizing the performance of the catalyst by applying several additional catalysts in the reactions was firstly done. Among those catalysts, KOH and H2SO4 showed significant impacts on the yields of the transvinylation reactions. It increased to 96 % when KOH was added and to 95 % when H2SO4 was added, compared to only 66 % when palladium(II) acetate alone was employed. Adding either KOH or H2SO4 along with the primary catalyst of palladium(II) acetate in transvinylation reactions of hydroxycinnamic acids gave the desired products in good yields. This proved that palladium(II) acetate was capable of catalyzing the transvinylation reactions of hydroxycinnamic acid and its derivatives to produce some vinyl esters.

  已经完成了关于醋酸钯（II）在羟基肉桂酸的转乙烯基化反应中作为催化剂的应用研究。这项研究旨在评估醋酸钯（II）作为汞（II）催化剂的更安全替代品在羟基肉桂酸及其衍生物的转乙烯基化反应中的能力。首先通过在反应中添加几种额外的催化剂来优化催化剂的性能。在这些催化剂中，KOH和H2SO4对转乙烯基化反应的产量有显著影响。与单独使用醋酸钯（II）时只有66%的产量相比，添加KOH时产量增加到96%，添加H2SO4时增加到95%。在羟基肉桂酸的转乙烯基化反应中，添加KOH或H2SO4以及主要催化剂醋酸钯（II）都能获得高产量的理想产物。这证明醋酸钯（II）能够催化羟基肉桂酸及其衍生物的转乙烯基化反应，生成一些乙烯酯。
• Accessing columbianetin-containing natural products via a domino on-water, in-water process
  作者：Kaitlin D. Beare、Christopher S.P. McErlean

  DOI：10.1016/j.tetlet.2012.11.150

  日期：2013.2

  A domino on-water, in-water process has been developed for the rapid and efficient synthesis of (+/-)-columbianetin. This highlights the operational simplicity of on-water chemistry. The domino process forms the key step in the synthesis of the columbianetin-containing natural products (+/-)-columbianetin acetate, (+/-)-zosimin, (+/-)-libanorin and (+/-)-angelmarin. (C) 2013 Elsevier Ltd. All rights reserved.