((5-ethynyl-1,3-phenylene)bis(oxy))bis(tert-butyldimethylsilane) | 187803-42-5

• 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: ((5-ethynyl-1,3-phenylene)bis(oxy))bis(tert-butyldimethylsilane)
• 英文别名: Tert-butyl-[3-[tert-butyl(dimethyl)silyl]oxy-5-ethynylphenoxy]-dimethylsilane
• CAS: 187803-42-5
• 化学式: C₂₀H₃₄O₂Si₂
• 分子量: 362.66
• InChiKey: WUTYHQFETAHNAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((5-ethynyl-1,3-phenylene)bis(oxy))bis(tert-butyldimethylsilane) 在 四丁基氟化铵 作用下， 以97%的产率得到5-乙炔-1,3-苯二醇
  参考文献：
  名称：

  Desilylation Reactions of Poly[(t-butyldimethylsilyloxy)phenylacetylene]s

  摘要：

  将聚[4-(叔丁基二甲基甲硅烷氧基)-2-三甲基甲硅烷基苯乙炔]和聚[5-乙炔基-3-(叔丁基二甲基甲硅烷氧基)苯基(R)-2-苯基丙酸酯]用Bu4NF在THF中脱甲硅烷基化。该溶液根据芳香吊坠的结构改变颜色。

  DOI：

  10.1246/cl.1992.2261
• 作为产物：
  描述：

  3,5-二羟基苯甲醛 在 咪唑 、 叔丁基二甲基氯硅烷 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.58h， 生成 ((5-ethynyl-1,3-phenylene)bis(oxy))bis(tert-butyldimethylsilane)
  参考文献：
  名称：

  δ-Viniferin 类似物和电子等排体的合成和抗菌活性

  摘要：

  天然二苯乙烯脱氢-δ-葡萄素含有苯并呋喃核心，最近被认为是一种有前途的抗菌剂。为了定义与其活性相关的结构元素，我们修饰了苯并呋喃环 C5 处的苯乙烯基部分。在本文中，我们报告了二苯乙烯衍生的 2,3-二芳基-5-取代苯并呋喃的构建，这使我们能够制备一系列脱氢-δ-葡萄苷类似物。评估了合成化合物针对金黄色葡萄球菌ATCC29213 的抗菌活性。简化的类似物 5,5'-(2-(4-羟基苯基)苯并呋喃-3,5-二基)双(苯-1,3-二醇)，通过三步从 4-溴-2-碘苯酚 (63%总产率），成为进一步研究的有希望的候选者（MIC = 4 µg/mL）。

  DOI：

  10.3390/molecules26247594

文献信息

• Facile Synthesis of Natural Moracin Compounds using Pd(OAc)₂/P(^tBu)₃-HBF₄as a Sonogashira Coupling Reagent
  作者：Jae Jun Lee、So-Ra Yun、Jong-Gab Jun

  DOI：10.5012/bkcs.2014.35.12.3453

  日期：2014.12.20

  An efficient and practical synthesis of natural moracins, which have diverse range of biological properties including anticancer, antioxidant, and antibacterial activities, has been achieved using $Pd(OAc)_2/P(^tBu)_3-HBF_4$ as a Sonogashira coupling reagent which solved the unreactive problems in case of higher electron density of haloaryl compounds in the reaction. Lowering electron density of halophenol with acetylation and changing Sonogashira coupling reagent from $PdCl_2(PPh_3)_2$ to $Pd(OAc)_2/P(^tBu)_3-HBF_4$ smoothly produce the benzofuran structures in the syntheses of moracins M, N and S. The electron deficient halobenzaldehyde, however, easily forms the benzofuran using original Sonogashira conditions, and utilized for the first synthesis of moracin Y.

  一种高效实用的天然莫拉辛（moracins）合成方法已经实现，该类化合物具有抗癌、抗氧化和抗菌等多种生物活性。该合成使用了 $Pd(OAc)_2/P(^tBu)_3-HBF_4$ 作为Sonogashira耦合试剂，成功解决了在反应中卤代芳香化合物高电子密度所导致的不反应问题。通过对氯苯酚进行乙酰化以降低电子密度，并将Sonogashira耦合试剂从 $PdCl_2(PPh_3)_2$ 更换为 $Pd(OAc)_2/P(^tBu)_3-HBF_4$，顺利合成了莫拉辛M、N和S的苯并呋喃结构。然而，电子缺乏的卤代苯甲醛在原始Sonogashira条件下能容易地形成苯并呋喃，并用于首次合成莫拉辛Y。
• The first total synthesis of moracin O and moracin P, and establishment of the absolute configuration of moracin O
  作者：Navneet Kaur、Yan Xia、Yinglan Jin、Nguyen Tien Dat、Kondaji Gajulapati、Yongseok Choi、Young-Soo Hong、Jung Joon Lee、Kyeong Lee

  DOI：10.1039/b823340c

  日期：——

  The first total synthesis of the naturally occurring benzofurans, moracins O and P was achieved using a Sonogashira cross coupling reaction followed by in situ cyclization, and the absolute configuration of natural moracin O was established.

  利用 Sonogashira 交叉偶联反应和原位环化，首次实现了天然苯并呋喃、吗拉辛 O 和 P 的全合成，并确定了天然吗拉辛 O 的绝对构型。
• Synthesis and Photochemical Characteristics of Amphiphilic Enediyne Dendrimers
  作者：Nao Yoshimura、Atsuya Momotake、Yoshihiro Shinohara、Kayori Takahashi、Ritsuko Nagahata、Yoshinobu Nishimura、Tatsuo Arai

  DOI：10.1246/bcsj.82.723

  日期：2009.6.15

  give fluorescence quantum yield of 0.10―0.64, and they underwent efficient photochemical isomerization with quantum yields of 0.22―0.50 in THF. In water, other photochemical reactions took place. Fluorescence or triplet lifetimes were also strongly affected by dendrimer generation and solvent polarity. The structure―photochemical property relationship of new photoresponsive dendrimers is discussed.

  以纯顺式和反式异构体形式制备两亲性烯二炔核树枝状聚合物。所有树枝状大分子都具有荧光，荧光量子产率为0.10-0.64，它们在THF中进行了有效的光化学异构化，量子产率为0.22-0.50。在水中，发生了其他光化学反应。荧光或三重态寿命也受到树枝状聚合物生成和溶剂极性的强烈影响。讨论了新型光响应树枝状大分子的结构-光化学性质关系。
• End-Cap Stabilized Oligoynes: Model Compounds for the Linear sp Carbon Allotrope Carbyne
  作者：Thomas Gibtner、Frank Hampel、Jean-Paul Gisselbrecht、Andreas Hirsch

  DOI：10.1002/1521-3765(20020118)8:2<408::aid-chem408>3.0.co;2-l

  日期：2002.1.18

  Three series of differently 3,5-disubstituted alpha,omega-diphenylpolyynes Ar-(CdropC)(n)-Ar (n=2, 4, 6, 8, 10) were synthesized under optimized Cadiot-Chodkiewicz conditions, isolated and completely characterized. These compounds can be considered as model substances for the hypothetical one-dimensional carbon allotrope carbyne C, The longest sp-carbon chain contains 20 atoms and is therefore the longest, purely organic polyyne studied with NMR techniques. Extinction coefficients over 600000m(-1)cm(-1) represent the highest measured quantitative values for that compound class so far. Comparisons with previous investigations and electrochemical studies allow the assignment of absorption for both wavelength regions structuring the UV/Vis spectra. Based on the trends in the spectroscopic behaviour of those molecules with increasing chain length. electronic as well as the NMR properties of carbyne are predicted, in line with our previously reported results. The observed stability mise the. properties pro synthesis of even longer polyynes.
• Synthesis, electrochemistry and anticancer activity of novel ferrocenyl phenols prepared via azide-alkyne 1,3-cycloaddition reaction
  作者：Damian Plażuk、Błażej Rychlik、Andrzej Błauż、Sławomir Domagała

  DOI：10.1016/j.jorganchem.2012.05.042

  日期：2012.9

  A series of monophenols and diphenols containing the ferrocene-C-triazolyl and ferrocene-N-triazolyl bond were prepared in a cycloaddition reaction of ethynylferrocene with aryl and benzyl azides and in a reaction of azidoferrocene with phenylacetylenes, respectively. The anticancer activity of the prepared compounds against hormone-dependent (MCF-7) and hormone-independent (HCC38) breast cancer cell lines was studied. The investigated compounds exhibited moderate anticancer activity against hormone-independent (IC50 similar to 15-48 mu M) cancer cell line and low activity against hormone-dependent cancer cell line (IC50 similar to 84-98 mu M). (C) 2012 Elsevier B. V. All rights reserved.