7-chloro-3-hydroxy-5,8-dioxo-5,8-dihydro-naphthalene-1-carboxylic acid ethyl ester | 1002331-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-chloro-3-hydroxy-5,8-dioxo-5,8-dihydro-naphthalene-1-carboxylic acid ethyl ester
• 英文别名: Ethyl 7-chloro-3-hydroxy-5,8-dioxonaphthalene-1-carboxylate
• CAS: 1002331-87-4
• 化学式: C₁₃H₉ClO₅
• 分子量: 280.664
• InChiKey: HGWLFASISXTYOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	7-benzyloxy-3-hydroxy-5,8-dioxo-5,8-dihydronaphthalene-1-carboxylic acid ethyl ester	1002331-88-5	C20H16O6	352.343

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  C₃₁H₅₂Cl₂O₆Si₂ 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以3.76 g的产率得到7-chloro-3-hydroxy-5,8-dioxo-5,8-dihydro-naphthalene-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.