(9-Benzyloxy-1-hydroxy-4-methoxy-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-acetic acid tert-butyl ester | 1026372-60-0

• 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-Benzyloxy-1-hydroxy-4-methoxy-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-acetic acid tert-butyl ester
• 英文别名: tert-butyl 2-(3-hydroxy-9-methoxy-4-phenylmethoxy-1H-benzo[f][2]benzofuran-3-yl)acetate
• CAS: 1026372-60-0
• 化学式: C₂₆H₂₈O₆
• 分子量: 436.505
• InChiKey: TYUCHAJDLCOCCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (9-Benzyloxy-1-hydroxy-4-methoxy-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-acetic acid tert-butyl ester 在 10percent Pd/C 三乙基硅烷 、 1,4-环己二烯 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 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+
• 作为产物：
  描述：

  9-Hydroxy-4-methoxy-3H-naphtho[2,3-c]furan-1-one 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 12.75h， 生成 (9-Benzyloxy-1-hydroxy-4-methoxy-1,3-dihydro-naphtho[2,3-c]furan-1-yl)-acetic acid tert-butyl ester
  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

• 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.