4-((S)-2-hydroxybut-3-ynyloxy)benzoic acid | 245093-79-2

• 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: 4-((S)-2-hydroxybut-3-ynyloxy)benzoic acid
• 英文别名: 4-[(2S)-2-hydroxybut-3-ynoxy]benzoic acid
• CAS: 245093-79-2
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: BHYJLEDUCTYKHX-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((S)-2-hydroxybut-3-ynyloxy)benzoic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 正己烷 为溶剂， 反应 3.0h， 以93%的产率得到methyl 4-(2-hydroxybutynoxy)benzoate
  参考文献：
  名称：

  New Bioactive Rosigenin Analogues and Aromatic Polyketide Metabolites from the Freshwater Aquatic Fungus Massarina tunicata

  摘要：

  Four new rosigenin analogues (massarigenins A-D; 1-4) and two new aromatic polyketide-derived secondary metabolites (massarinins A and B; 6, 7) and have been isolated from the freshwater aquatic fungus Massarina tunicata. The structures of these compounds were determined primarily by analysis of NMR data, and that of compound 1 was verified by X-ray crystallography. The known compound 4-(2-hydroxybutynoxy)benzoic acid (11) was also obtained, and its absolute stereochemistry was assigned. Several of these metabolites showed antibiotic activity against Gram-positive bacteria.

  DOI：

  10.1021/np020342d
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到4-((S)-2-hydroxybut-3-ynyloxy)benzoic acid
  参考文献：
  名称：

  On the structure of penipratynolene and WA

  摘要：

  The antipode of the structure proposed for the natural product penipratynolene in the literature was synthesized in high enantiopurity via an chiron approach and fully characterized. However, substantial differences were observed between the physical and spectroscopic data of the synthetic sample and those reported for the natural penipratynolene. Possible causes for the discrepancies are proposed on the basis of acquisition and comparison of additional data. The present work also provides the only piece of synthetic evidence for ail antifungal natural product WA, the corresponding acid of the antipode of natural penipratynolene. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.073

文献信息

• On the structure of penipratynolene and WA
  作者：Ya-Jun Jian、Yikang Wu

  DOI：10.1016/j.tet.2009.11.073

  日期：2010.1

  The antipode of the structure proposed for the natural product penipratynolene in the literature was synthesized in high enantiopurity via an chiron approach and fully characterized. However, substantial differences were observed between the physical and spectroscopic data of the synthetic sample and those reported for the natural penipratynolene. Possible causes for the discrepancies are proposed on the basis of acquisition and comparison of additional data. The present work also provides the only piece of synthetic evidence for ail antifungal natural product WA, the corresponding acid of the antipode of natural penipratynolene. (C) 2009 Elsevier Ltd. All rights reserved.
• New Bioactive Rosigenin Analogues and Aromatic Polyketide Metabolites from the Freshwater Aquatic Fungus <i>Massarina </i><i>t</i><i>unicata</i>
  作者：Hyuncheol Oh、Dale C. Swenson、James B. Gloer、Carol A. Shearer

  DOI：10.1021/np020342d

  日期：2003.1.1

  Four new rosigenin analogues (massarigenins A-D; 1-4) and two new aromatic polyketide-derived secondary metabolites (massarinins A and B; 6, 7) and have been isolated from the freshwater aquatic fungus Massarina tunicata. The structures of these compounds were determined primarily by analysis of NMR data, and that of compound 1 was verified by X-ray crystallography. The known compound 4-(2-hydroxybutynoxy)benzoic acid (11) was also obtained, and its absolute stereochemistry was assigned. Several of these metabolites showed antibiotic activity against Gram-positive bacteria.