[4-(8-benzyloxy-4-{5-[(4-benzyloxyphenyl)methoxycarbonylmethylene]-4-methoxy-2-oxo-2,5-dihydrofuran-3-yl}-2-oxo-2H-naphtho[1,8-bc]furan-6-yl)-3-methoxy-5-oxo-5H-furan-2-ylidene](4-benzyloxyphenyl)acetic acid methyl ester | 1002331-93-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [4-(8-benzyloxy-4-{5-[(4-benzyloxyphenyl)methoxycarbonylmethylene]-4-methoxy-2-oxo-2,5-dihydrofuran-3-yl}-2-oxo-2H-naphtho[1,8-bc]furan-6-yl)-3-methoxy-5-oxo-5H-furan-2-ylidene](4-benzyloxyphenyl)acetic acid methyl ester
• 英文别名: methyl (2E)-2-[3-methoxy-4-[9-[(5E)-4-methoxy-5-[2-methoxy-2-oxo-1-(4-phenylmethoxyphenyl)ethylidene]-2-oxofuran-3-yl]-3-oxo-11-phenylmethoxy-2-oxatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaen-6-yl]-5-oxofuran-2-ylidene]-2-(4-phenylmethoxyphenyl)acetate
• CAS: 1002331-93-2
• 化学式: C₆₀H₄₄O₁₅
• 分子量: 1005.0
• InChiKey: GYUVFHFTSAVSMA-IELRNQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  75
• 可旋转键数：
  19
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  178
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [4-(8-benzyloxy-4-{5-[(4-benzyloxyphenyl)methoxycarbonylmethylene]-4-methoxy-2-oxo-2,5-dihydrofuran-3-yl}-2-oxo-2H-naphtho[1,8-bc]furan-6-yl)-3-methoxy-5-oxo-5H-furan-2-ylidene](4-benzyloxyphenyl)acetic acid methyl ester 在 碘代三甲硅烷 作用下， 以 氘代氯仿 为溶剂， 反应 264.0h， 以28%的产率得到8-羟基-4,6-双[(5E)-5-(alpha-羧基-4-羟基苄亚基)-4-羟基-2,5-二氢-2-氧代呋喃-3-基]-2H-萘并[1,8-bc]呋喃-2-酮
  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：

  {4-[3-benzyloxy-7-{5-[(4-benzyloxyphenyl)methoxycarbonylmethylene]-4-methoxy-2-oxo-2,5-dihydrofuran-3-yl}-4-hydroxy-5-(pyrrolidine-1-carbonyl)naphthalen-1-yl]-3-methoxy-5-oxo-5H-furan-2-ylidene}(4-benzyloxyphenyl)acetic acid methyl ester 在 溶剂黄146 作用下， 反应 2.0h， 以74%的产率得到[4-(8-benzyloxy-4-{5-[(4-benzyloxyphenyl)methoxycarbonylmethylene]-4-methoxy-2-oxo-2,5-dihydrofuran-3-yl}-2-oxo-2H-naphtho[1,8-bc]furan-6-yl)-3-methoxy-5-oxo-5H-furan-2-ylidene](4-benzyloxyphenyl)acetic acid methyl 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.