黄木亭 | 84-99-1

• 物质功能分类: 天然产物 - 香豆素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 黄木亭
• 英文名称: xanthoxyletin
• 英文别名: xanthoxylethin；xanthoxylatin；xanthoxylin N；5-methoxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-one；5-Methoxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-on；5-methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b;5,4-b']dipyran-2-one；5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-8-one
• CAS: 84-99-1
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: JSJIIHRNDMLJGK-UHFFFAOYSA-N

物化性质

• 熔点：
  134-135℃ (ethanol )
• 沸点：
  321.52°C (rough estimate)
• 密度：
  1.1178 (rough estimate)
• LogP：
  3.640 (est)
• 物理描述：
  Solid
• 溶解度：
  1.55e-04 M

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099
• 储存条件：
  储存条件：2-8℃，需保持干燥并密封。

制备方法与用途

Xanthoxyletin是一种香豆素，可以从花椒属和克劳森属中分离得到。它具有抗氧化和抗炎活性。

黄嘌呤对癌细胞具有细胞毒性，可以诱导细胞凋亡和坏死。黄烷氧基内皮素则可用于研究癌症和炎症。

反应信息

• 作为反应物：
  描述：

  黄木亭 在 Amberlyst-15 (H⁺) resin 、 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Natural Product-like Combinatorial Libraries Based on Privileged Structures. 3. The “Libraries from Libraries” Principle for Diversity Enhancement of Benzopyran Libraries

  摘要：

  As described in the preceding two papers, our interest in the construction of natural and natural product-like libraries for chemical biology studies led to the development of a new solid-phase cycloloading strategy for the construction of substituted benzopyrans. Herein, we report a parallel solution-phase method that facilitates the enhancement of both the size and diversity of these non-oligomeric benzopyran libraries using the "libraries from libraries" principle. We examine the rationale behind the use of this tandem strategy to construct discrete small molecule libraries, and describe the development of a polymer-assisted solution-phase (PASP) methodology necessary to effect the required transformations. Once developed, this chemistry is applied to two demonstration libraries.

  DOI：

  10.1021/ja0020355
• 作为产物：
  描述：

  5-Methoxy-2,2-dimethyl-7-chromanon 在 盐酸 、 palladium diacetate 、 氢氧化钾 、 甲酸 、 sodium acetate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 乙醇 、 苯 为溶剂， 反应 33.0h， 生成 黄木亭
  参考文献：
  名称：

  Atom Economy. Palladium-Catalyzed Formation of Coumarins by Addition of Phenols and Alkynoates via a Net C−H Insertion

  摘要：

  A strategy to achieve ortho substitution of phenols initiated by an ortho-palladation to create coumarins was examined. Indeed, treatment of alkynoates with electron-rich phenols in the presence of a palladium catalyst and an acid does generate coumarins. The scope of the reaction with respect to the phenol and the alkynoates is defined. With unsymmetrical aromatic substrates, generally good regioselectivity that reflects the HOMO coefficients can be observed. In the course of these studies, numerous important naturally occurring coumarins have been synthesized, including fraxinol methyl ether, ayapin, herniarin, xanthoxyletin, and alloxanthoxyletin. The fact that a Pd(0) is the precatalyst rather than a Pd(+2) species and that an acid that reduces Pd(+2) salts, formic acid, functions better than other carboxylic acids raises doubts about the initial working hypothesis. A novel mechanism involving a palladium phenoxide formed from a hydridopalladium carboxylate and phenol is invoked to rationalize the results.

  DOI：

  10.1021/ja0286573

文献信息

• 4-SUBSTITUTED COUMARIN DERIVATIVES AND PREPARATION METHODS AND USES THEREOF
  申请人：CHEN Lijuan

  公开号：US20180282315A1

  公开（公告）日：2018-10-04

  The present invention pertains to the field of chemical medicine, particularly to 4-substituted coumarin derivatives and preparation methods and applications thereof. The invention provides 4-substituted coumarin derivatives with a structural formula as shown in Formula I. The invention also provides preparation methods and applications for the above 4-substituted coumarin derivatives. The compounds provided in the invention have strong anti-tumor activity with IC50 for plural tumor cell lines between 0.01-5 nM, and it also performs better to inhibit microtubule polymerization and has diversified biological activities and low toxicity, providing new options for drug-sensitive and drug-resistant tumor cells.

  本发明涉及化学药品领域，特别是4-取代香豆素衍生物及其制备方法和应用。该发明提供了具有如公式I所示结构式的4-取代香豆素衍生物。该发明还提供了上述4-取代香豆素衍生物的制备方法和应用。本发明提供的化合物在多种肿瘤细胞系中具有强大的抗肿瘤活性，IC50在0.01-5 nM之间，并且在抑制微管聚合方面表现更好，具有多样化的生物活性和低毒性，为药物敏感和耐药肿瘤细胞提供了新选择。
• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans
  作者：K. C. Nicolaou、J. A. Pfefferkorn、A. J. Roecker、G.-Q. Cao、S. Barluenga、H. J. Mitchell

  DOI：10.1021/ja002033k

  日期：2000.10.1

  report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran

  在此，我们报告了一种基于特权结构原理设计和构建天然和天然产物类库的新策略，该术语最初用于描述能够与各种不相关的分子靶标相互作用的结构基序。讨论了天然产物中此类特权结构的鉴定，随后选择 2,2-二甲基苯并吡喃部分作为通过该策略构建类天然产物库的初始模板。最初，采用独特的环加载策略开发了苯并吡喃基序的新型固相合成，该策略依赖于使用新的聚苯乙烯基溴化硒树脂。一旦确定了这些苯并吡喃的加载、加工和裂解，
• Synthesis of Linear Pyranocoumarins: Xanthoxyletin, 4-Methyl-xanthyletin, and 4-Phenylxanthyletin
  作者：Vindo Kumar Ahluwalia、Krishna Bhat、Chandra Prakash、Shashi Bala

  DOI：10.1246/bcsj.53.1070

  日期：1980.4

  A convenient synthesis of linear pyranocoumarins (2H,8H-benzo[1,2-b: 5,4-b′]dipyran-2-ones), viz., xanthoxyletin, 4-methylxanthyletin and 4-phenylxanthyletin is described which uses blocking the 8-position of appropriate 7-hydroxycoumarin derivatives with iodine and 1,1-dimethyl-2-propynylation followed by cyclisation.

  描述了一种方便合成线性吡喃香豆素（2H,8H-苯并[1,2-b:5,4-b′]二吡喃-2-酮），即黄栌素、4-甲基黄栌素和4-苯基黄栌素的方法，该方法通过在适当的7-羟基香豆素衍生物的8位位置用碘阻断，并进行1,1-二甲基-2-丙炔基化，然后进行环化反应。
• Constituents of Domestic Citrus Plants. Part XVI. Five New Pyranocoumarins from Some Citrus Plants.
  作者：Yuko TAKEMURA、Yumiko NAKATA、Miki AZUMA、Motoharu JU-ICHI、Masayoshi OKANO、Narihiko FUKAMIYA、Mitsuo OMURA、Chihiro ITO、Kiyomi NAKAGAWA、Hiroshi FURUKAWA

  DOI：10.1248/cpb.41.1530

  日期：——

  Five new pyranocoumarins, named cis-5-methoxydecursidinol (1), trans-5-methoxydecursidinol (2), cis-hassanin (4), trans-hassanin (5), and hassanidin (7), were isolated from the roots of some Citrus plants and their structures were elucidated by spectroscopic methods and chemical derivation from known coumarins.

  从一些柑橘类植物的根中分离出了五种新的吡喃香豆素，分别命名为顺式-5-甲氧基癸基香豆素醇（1）、反式-5-甲氧基癸基香豆素醇（2）、顺式-哈萨宁（4）、反式-哈萨宁（5）和哈萨宁（7），并通过光谱方法和已知香豆素的化学衍生方法阐明了它们的结构。
• Process for production of vinyl chloride polymer
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP0172427A2

  公开（公告）日：1986-02-26

  This process is a process for production of a vinyl chloride polymer by suspension polymerization or emulsion polymerization of vinyl chloride monomer or a mixture of vinyl chloride monomer with a vinyl monomer copolymerizable with said vinyl chloride monomer in an aqueous medium, characterized in that the polymerization is carried out in a polymerizer, the inner wall surface and portions of the auxiliary equipment thereof which may come into contact with the monomer during polymerization being previously coated with a scaling preventive comprising at least one selected from dyes, pigments and aromatic or heterocyclic compounds having at least 5 conjugated π bonds, while controlling the chloride ion concentration in the reaction mixture to not higher than 100 ppm. According to said process, scaling onto the inner wall surface of a polymerizer, etc. during polymerization can be prevented effectively and surely.

  该工艺是通过氯乙烯单体或氯乙烯单体与可与所述氯乙烯单体共聚的乙烯基单体混合物在水介质中进行悬浮聚合或乳液聚合来生产氯乙烯聚合物的工艺，其特征在于聚合是在聚合器中进行的、内壁表面及其辅助设备中可能在聚合过程中与单体接触的部分事先涂上一层防垢剂，该防垢剂至少包括一种选自染料、颜料和至少有 5 个共轭 π 键的芳香族或杂环化合物的防垢剂，同时控制反应混合物中的氯离子浓度不高于 100 ppm。根据上述工艺，可有效、可靠地防止聚合过程中聚合器等内壁表面结垢。

表征谱图