安纽洛灵 | 3988-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 安纽洛灵
• 英文名称: (E)-2-(3,4-dimethoxystyryl)-5-(4-methoxyphenyl)oxazole
• 英文别名: annuloline；2-(3,4-dimethoxy-trans-styryl)-5-(4-methoxy-phenyl)-oxazole；2-(3,4-dimethoxy-styryl)-5-(4-methoxy-phenyl)-oxazole；2-(3,4-Dimethoxy-trans-styryl)-5-(4-methoxy-phenyl)-oxazol；Annulolin；2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-5-(4-methoxyphenyl)-1,3-oxazole
• CAS: 3988-51-0
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: VGJRJYYLGKAWDE-VZUCSPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  53.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 copper(l) iodide 、 trans-1,2-Diethylcyclohexane 、 potassium carbonate 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 安纽洛灵
  参考文献：
  名称：

  Synthesis and evaluation of photophysical properties of Series of π-conjugated oxazole dyes

  摘要：

  Incorporation of pi-conjugated spacers at the 2 or 5 position of a 2,5-disubstitutedaryloxazole led to new series of fluorescent dyes. They show emissions from visible to 700 nm along with significant Stokes shift up to 208 nm and a strong solvatochromic fluorescence. These compounds are easily accessible in one step through direct C-H bond functionalization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.037

文献信息

• Ligand promoted Pd-catalyzed dehydrogenative alkenylation of hetereoarenes
  作者：Wei-Chih Lee、Ting-Hsuan Wang、Tiow-Gan Ong

  DOI：10.1039/c3cc48750d

  日期：——

  An efficient Pd-catalyzed cross-dehydrogenative coupling of heteroarenes with alkenes has been developed. This alkenylation paradigm encompasses a wide range of substrates and provides a straightforward approach toward C2-E-alkenylated azole motifs.

  已开发出一种高效的Pd催化的杂环烃与烯烃的交叉脱氢偶联反应。这种烯基化范式涵盖了广泛的底物，并提供了一种直接的方法来合成C2-E-烯基化咪唑基团。
• Stereoselective Direct Copper-Catalyzed Alkenylation of Oxazoles with Bromoalkenes
  作者：François Besselièvre、Sandrine Piguel、Florence Mahuteau-Betzer、David S. Grierson

  DOI：10.1021/ol801512q

  日期：2008.9.18

  A copper-catalyzed direct alkenylation of oxazoles with bromoalkenes has been developed. The method is both regio- and stereoselective and tolerates a variety of functional groups. A wide range of 2-E-vinyl-substituted oxazoles were obtained in high yields including the highly fluorescent alkaloid annuloline.

  已经开发了铜催化的恶唑与溴代烯烃的直接烯基化。该方法具有区域选择性和立体选择性，并且可以耐受多种功能基团。以高收率获得了广泛的2-E-乙烯基取代的恶唑，包括高度发荧光的生物碱环烷。
• Sustainable Production of Bioactive Molecules from C‐Lignin‐Derived Propenylcatechol
  作者：Weihong Song、Qinglian Du、Xiancheng Li、Shuizhong Wang、Guoyong Song

  DOI：10.1002/cssc.202200646

  日期：2022.7.21

  Castoff to bioactive molecules: The diversified functionalization of propenylcatechol, a direct depolymerized product from naturally occurring catechyl lignin, resulted in a series of functional molecular skeletons. Starting from castor seed coats, annuloline (natural product) and CC-5079 (antitumor) were synthesized with a superior step-efficiency to that of reported synthetic routes.

  丢弃到生物活性分子：丙烯基儿茶酚是天然存在的儿茶基木质素的直接解聚产物，其多样化的功能化产生了一系列功能性分子骨架。从蓖麻种皮开始，以比报道的合成路线更高的步骤效率合成了annuloline（天然产物）和CC-5079 （抗肿瘤）。
• Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization
  作者：Chi Wai Cheung、Stephen L. Buchwald

  DOI：10.1021/jo301332s

  日期：2012.9.7

  A copper(11)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.
• Lewis acid promoted reactions of diazocarbonyl compounds. 3. Synthesis of oxazoles from nitriles through intermediate .beta.-imidatoalkenediazonium salts
  作者：Michael P. Doyle、William E. Buhro、James G. Davidson、Robert C. Elliott、James W. Hoekstra、Mark Oppenhuizen

  DOI：10.1021/jo01306a023

  日期：1980.8