(+)-ambuic acid | 340774-69-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-ambuic acid
• 英文别名: ambuic acid；(E)-4-[(1R,5R,6R)-3-[(E)-hept-1-enyl]-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid
• CAS: 340774-69-8
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: UDSQZJMGPSRCEM-HDKVZZTHSA-N

物化性质

• 溶解度：
  DMSO：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1'R,4'S,4'aS,6'S,7'R,8'aR)-7'-allyl-1',4',4'a,8'a-tetrahydro-(1',4'-methanonaphtho-6',7'-epoxy)-5',8'-dione 在 咪唑 、 四(三苯基膦)钯 、 二苯醚 、 1,2-二溴四氯乙烷 、 氢氟酸 、 二异丁基氢化铝 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 26.05h， 生成 (+)-ambuic acid
  参考文献：
  名称：

  Total Synthsis of (+)-Ambuic Acid: α-Bromination with 1,2-Dibromotetrachloroethane

  摘要：

  Total synthesis of (+)-ambuic acid has been accomplished from the readily available stereocontrolled Diels-Alder adduct of cyclopentadiene and iodo-1,4-benzoquinone monoketal through an efficient series of steps. A new method for the highly commendable synthesis of alpha-brominated Diels-Alder adduct is described.

  DOI：

  10.1021/jo202357s

文献信息

• Total Synthesis of the Quinone Epoxide Dimer (+)-Torreyanic Acid:  Application of a Biomimetic Oxidation/Electrocyclization/Diels−Alder Dimerization Cascade¹
  作者：Chaomin Li、Richard P. Johnson、John A. Porco

  DOI：10.1021/ja021396c

  日期：2003.4.1

  An asymmetric synthesis of the quinone epoxide dimer (+)-torreyanic acid (48) has been accomplished employing [4 + 2] dimerization of diastereomeric 2H-pyran monomers. Synthesis of the related monomeric natural product (+)-ambuic acid (2) has also been achieved which establishes the biosynthetic relationship between these two natural products. A tartrate-mediated nucleophilic epoxidation involving

  醌环氧化物二聚体 (+)-torreyanic 酸 (48) 的不对称合成已使用非对映体 2H-吡喃单体的 [4 + 2] 二聚化完成。相关单体天然产物 (+)-安布酸 (2) 的合成也已实现，这建立了这两种天然产物之间的生物合成关系。涉及羟基方向的酒石酸盐介导的亲核环氧化促进了关键手性醌单环氧化物中间体的不对称合成。还对基于torreyanic酸核心结构的模型二聚体进行了热解实验，并且观察到了非对映异构体2H-吡喃的平衡逆向Diels-Alder反应过程。
• ANTI-VIRULANCE COMPOSITIONS AND METHODS
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US20150265550A1

  公开（公告）日：2015-09-24

  A method of reducing the virulence of a bacterium that expresses accessory gene regulator A (AgrA) or an ortholog of AgrA includes administering to the bacterium an amount of a pharmaceutical composition effective to inhibit the synthesis of one or more virulence factors by the bacterium, the pharmaceutical composition including an AgrA antagonist.

  一种减少表达附属基因调节器A（AgrA）或AgrA同源物的细菌的毒性的方法，包括向细菌投入一定量的药物组合物，以抑制细菌合成一种或多种毒力因子，所述药物组合物包括一种AgrA拮抗剂。
• Pestalotiopsis microsporia isolates and compounds derived therefrom
  申请人：——

  公开号：US20040009573A1

  公开（公告）日：2004-01-15

  The present invention relates to the novel isolated 12-30 strain of Pestalotiopsis microspora capable of producing novel antioxidant and antimycotic agents. The present invention also relates to the novel isolated 3,5,7 trisubstituted isobenzofuranone and derivatives thereof, methods of isolating the novel isobenzofuranone from cultures P. microspora 12-30, and to novel uses of the compound as an antioxidant and antimycotic agent. The present invention further relates to a novel 1,5,7 trisubstituted 1,3-dihydroisobenzofuran and derivatives thereof, methods of isolating this novel compound from cultures of Pestalotiopsis microspora 12-30, and to uses thereof.

  本发明涉及分离出的 12-30 株新型 Pestalotiopsis microspora 本发明涉及能够产生新型抗氧化剂和抗霉菌剂的新型分离菌株 Pestalotiopsis microspora 12-30。本发明还涉及新型分离的 3,5,7-三取代异苯并呋喃酮及其衍生物、从微孢子虫培养物中分离新型异苯并呋喃酮的方法。 P. microspora 12-30 中分离新型异苯并呋喃酮的方法，以及该化合物作为抗氧化剂和抗真菌剂的新用途。本发明进一步涉及一种新型的 1，5，7 三取代的 1，3-二氢异苯并呋喃及其衍生物，从小孢子虫 Pestalotiopsis 的培养物中分离这种新型化合物的方法。 Pestalotiopsis microspora 12-30 及其用途。
• NMR Crystallography Methods for Three-Dimensional Structure Determination
  申请人：HEIDER Elizabeth M.

  公开号：US20130328558A1

  公开（公告）日：2013-12-12

  The invention relates to new uses of nuclear magnetic resonance (NMR) crystallography methods to determine and/or characterize the three-dimensional structure of compounds of interest.
• ANTI-VIRULENCE COMPOSITIONS AND METHODS
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US20180021277A1

  公开（公告）日：2018-01-25

  A method of treating a bacterial infection in a subject in need thereof includes administering to the subject an AgrA antagonist.