7-benzyloxy-3-hydroxy-5,8-dioxo-5,8-dihydronaphthalene-1-carboxylic acid ethyl ester | 1002331-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-benzyloxy-3-hydroxy-5,8-dioxo-5,8-dihydronaphthalene-1-carboxylic acid ethyl ester
• 英文别名: Ethyl 3-hydroxy-5,8-dioxo-7-phenylmethoxynaphthalene-1-carboxylate
• CAS: 1002331-88-5
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: PRFJEJZDYJIWEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-3-hydroxy-5,8-dioxo-5,8-dihydronaphthalene-1-carboxylic acid ethyl ester 在 sodium dithionite 作用下， 以 水 、 丙酮 为溶剂， 反应 0.25h， 生成 C₂₀H₁₈O₆
  参考文献：
  名称：

  Total Synthesis of Norbadione A

  摘要：

  [GRAPHICS]A short, convergent synthesis of the mushroom pigment norbadione A is described. The construction of an appropriately substituted naphtholactone intermediate. involved a regioselective Diels-Alder reaction between a bis(triisopropylsilyloxy)diene and 2,6-dichlorobenzo-1,4-quinone. A double Suzuki-Miyaura cross-coupling between a diboronate and two identical enol triflates was another key feature of the synthesis.

  DOI：

  10.1021/jo702106u
• 作为产物：
  描述：

  7-chloro-3-hydroxy-5,8-dioxo-5,8-dihydro-naphthalene-1-carboxylic acid ethyl ester 、 苯甲醇 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 以77%的产率得到7-benzyloxy-3-hydroxy-5,8-dioxo-5,8-dihydronaphthalene-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Total Synthesis of Norbadione A

  摘要：

  [GRAPHICS]A short, convergent synthesis of the mushroom pigment norbadione A is described. The construction of an appropriately substituted naphtholactone intermediate. involved a regioselective Diels-Alder reaction between a bis(triisopropylsilyloxy)diene and 2,6-dichlorobenzo-1,4-quinone. A double Suzuki-Miyaura cross-coupling between a diboronate and two identical enol triflates was another key feature of the synthesis.

  DOI：

  10.1021/jo702106u

文献信息

• Total Synthesis of Norbadione A
  作者：Yann Bourdreux、Stéphanie Nowaczyk、Célia Billaud、Aurélie Mallinger、Catherine Willis、Marine Desage-El Murr、Loïc Toupet、Claude Lion、Thierry Le Gall、Charles Mioskowski

  DOI：10.1021/jo702106u

  日期：2008.1.1

  [GRAPHICS]A short, convergent synthesis of the mushroom pigment norbadione A is described. The construction of an appropriately substituted naphtholactone intermediate. involved a regioselective Diels-Alder reaction between a bis(triisopropylsilyloxy)diene and 2,6-dichlorobenzo-1,4-quinone. A double Suzuki-Miyaura cross-coupling between a diboronate and two identical enol triflates was another key feature of the synthesis.