monaspilosin | 1040756-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: monaspilosin
• 英文别名: 2-(4-hydroxyphenyl)ethyl 2-phenylacetate
• CAS: 1040756-53-3
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: LEHFWRIESDDBMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 生成 monaspilosin
  参考文献：
  名称：

  Cytotoxic naphthoquinone and a new succinate ester from the soil fungus Fusarium solani PSU-RSPG227

  摘要：

  A new naphthoquinone, solaninaphthoquione (1), and a new succinate ester derivative, 4-(4-hydroxyphenethoxy)-4-oxobutanoic acid (2), were isolated from the soil fungus Fusarium solani PSU-RSPG227 together with five previously reported compounds; javanicin (3), monaspilosin (4), aspergillol B (5), tyrosol (6) and 4- hydroxyphenylacetic acid (7). Their structures were elucidated primarily by NMR spectroscopic data. Due to paucity of materials, compounds 2, 4 and 5 as well as analogues of 5 were prepared for biological activity evaluation. Compound 1 showed significant cytotoxic activity against breast cancer (MCF-7) cells and mild cytotoxic activity against oral human carcinoma (KB) cells (IC50 values of 21.3 and 22.6 mu M, respectively) compared to standard compounds. Compound 1 also displayed weak antimalarial activity (IC50 of 26.1 mu M). (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2014.11.018

文献信息

• A Lewis acid-promoted Pinner reaction
  作者：Dominik Pfaff、Gregor Nemecek、Joachim Podlech

  DOI：10.3762/bjoc.9.179

  日期：——

  Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward synthesis of acrylates and benzoates starting with acrylonitrile and benzonitrile, respectively, is similarly possible. Phenols are not acylated under these reaction conditions. The method has been used for the first total synthesis of the natural product monaspilosin. In the reaction of benzyl alcohols variable amounts of amides are formed in a Ritter-type side reaction.

  Carbonitriles和醇在Lewis酸促进的Pinner反应中反应生成羧酸酯。最佳结果是使用两当量的三甲基硅酰三氟甲烷作为Lewis酸。一次醇和脂肪族或苄基腈可以获得良好产率，但使用丙烯腈和苯甲腈分别合成丙烯酸酯和苯甲酸酯也同样可行。苯酚在这些反应条件下不会酰化。该方法已被用于天然产物单孢氨基脂的首次全合成。在苄醇的反应中，会形成不同量的酰胺，这是一种Ritter型的副反应。
• Kinetic Analysis as an Optimization Tool for Catalytic Esterification with a Moisture-Tolerant Zirconium Complex
  作者：Piret Villo、Oscar Dalla-Santa、Zoltán Szabó、Helena Lundberg

  DOI：10.1021/acs.joc.0c00235

  日期：2020.6.5

  This work describes the use of kinetics as a tool for rational optimization of an esterification process with down to equimolar ratios of reagents using a recyclable commercially available zirconocene complex in catalytic amounts. In contrast to previously reported group IV metal-catalyzed esterification protocols, the work presented herein circumvents the use of water scavengers and perfluorooctane

  这项工作描述了使用动力学作为合理优化酯化工艺的工具，使用可循环使用的市售锆茂复合物以催化量降低试剂的等摩尔比。与先前报道的第四族金属催化的酯化方案相反，本文介绍的工作规避了水清除剂和全氟辛烷磺酸盐（PFOS）配体的使用。提出了对运作机制的见解。