(9-Hydroxy-4-methoxy-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-acetic acid | 308277-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (9-Hydroxy-4-methoxy-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-acetic acid
• 英文别名: 2-(9-Hydroxy-4-methoxy-1,3-dihydrobenzo[f][2]benzofuran-1-yl)acetic acid
• CAS: 308277-86-3
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: IVYZBUZGYPGLDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (9-Hydroxy-4-methoxy-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-acetic acid 在 lead(IV) acetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以74%的产率得到(3aS,11aS)-6-Methoxy-3,3a-dihydro-5H-furo[3,2-b]naphtho[2,3-c]furan-2,11-dione
  参考文献：
  名称：

  Synthesis of the Functionalized Tricyclic Core of Lactonamycin by Oxidative Dearomatization

  摘要：

  [GRAPHICS]We report in this Letter a synthesis of the densely oxygenated CDEF ring system (27) corresponding to that found in the recently discovered antibiotic lactonamycin. The key steps in the synthesis consist of an intramolecular Wessely oxidative lactonization of acid 18, followed by a hydroxyl directed epoxidation of enol ether 21.

  DOI：

  10.1021/ol006531+
• 作为产物：
  描述：

  9-Hydroxy-4-methoxy-3H-naphtho[2,3-c]furan-1-one 在 10percent Pd/C 三乙基硅烷 、 1,4-环己二烯 、 potassium carbonate 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 17.75h， 生成 (9-Hydroxy-4-methoxy-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-acetic acid
  参考文献：
  名称：

  Synthesis of the Functionalized Tricyclic Core of Lactonamycin by Oxidative Dearomatization

  摘要：

  [GRAPHICS]We report in this Letter a synthesis of the densely oxygenated CDEF ring system (27) corresponding to that found in the recently discovered antibiotic lactonamycin. The key steps in the synthesis consist of an intramolecular Wessely oxidative lactonization of acid 18, followed by a hydroxyl directed epoxidation of enol ether 21.

  DOI：

  10.1021/ol006531+

文献信息

• Efficient Phenolic Oxidations to Construct ortho-Spirolactone Structures Using Oxo-Bridged Hypervalent Iodine(III) Compound
  作者：Yasuyuki Kita、Naoko Takenaga、Teruyoshi Uchiyama、Daishi Kato、Hiromichi Fujioka、Toshifumi Dohi

  DOI：10.3987/com-10-s(e)79

  日期：——

  The intramoleular ortho-spirocyclization of naphthols 1 bearing carboxylic acid moieties as internal nucleophiles using hypervalent iodine reagents is described. The use of the mu-oxo-bridged hypervalent iodine(III) compound is remarkably effective for this transformation, and spirolactones 2 were obtained in good to excellent yields using the mu-oxo-bis[trifluoroacetato(phenyl)iodine] 4 [PhI(OCOCF(3))O(OCOCF(3))IPh].
• Synthesis of the Functionalized Tricyclic Core of Lactonamycin by Oxidative Dearomatization
  作者：Christopher Cox、Samuel J. Danishefsky

  DOI：10.1021/ol006531+

  日期：2000.11.1

  [GRAPHICS]We report in this Letter a synthesis of the densely oxygenated CDEF ring system (27) corresponding to that found in the recently discovered antibiotic lactonamycin. The key steps in the synthesis consist of an intramolecular Wessely oxidative lactonization of acid 18, followed by a hydroxyl directed epoxidation of enol ether 21.