Methyl 5,5-dimethoxy-6-oxonaphthalene-1-carboxylate | 187935-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 5,5-dimethoxy-6-oxonaphthalene-1-carboxylate
• CAS: 187935-47-3
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: PNWQXQISPYBXHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-氰苯酞 、 Methyl 5,5-dimethoxy-6-oxonaphthalene-1-carboxylate 在 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 以87%的产率得到6-hydroxy-4,4-dimethoxy-4H-11-oxabenzo[def]chrysene-5,12-dione
  参考文献：
  名称：

  为benzonaphthopyranones的汇集合成串列环策略：的chartarin和全合成ö -methylhayumicinone

  摘要：

  豪瑟（Hauser）引发的串联环已开发出来，用于通过一锅操作形成两个环来快速区域特异性合成苯并萘并吡喃酮。这种策略已经被推广以benzonaphthopyranones 26，29，32，和35。它也已被用于沙丁鱼酯（3）和O-甲基干草umi酮（67）的短合成中。

  DOI：

  10.1016/j.tet.2008.01.039
• 作为产物：
  描述：

  甲醇 、 6-羟基萘-1-甲酸甲酯 在 碘苯二乙酸 作用下， 反应 24.0h， 以43%的产率得到Methyl 5,5-dimethoxy-6-oxonaphthalene-1-carboxylate
  参考文献：
  名称：

  A rapid access to hydroxylated benz[a]anthraquinones: Hypervalent iodine oxidation of β-naphthols

  摘要：

  Anionic annulation of phthalide sulfones 3 with quinone monoketals 6, accessible by phenyliodonium diacetate oxidation of naphthols 5, offers a high yielding regiospecific entry to benz[a]anthraquinones 8. Similar annulation of cyanophthalide 13 with 12, followed by photooxygenation of 14 results in a complementary route to the basic skeleton 15 of nonaromatic A-ring angucyclines. (C) 1997, Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01119-2

文献信息

• A rapid access to hydroxylated benz[a]anthraquinones: Hypervalent iodine oxidation of β-naphthols
  作者：Dipakranjan Mal、Harendra N. Roy、Nirmal K. Hazra、Susanta Adhikari

  DOI：10.1016/s0040-4020(96)01119-2

  日期：1997.2

  Anionic annulation of phthalide sulfones 3 with quinone monoketals 6, accessible by phenyliodonium diacetate oxidation of naphthols 5, offers a high yielding regiospecific entry to benz[a]anthraquinones 8. Similar annulation of cyanophthalide 13 with 12, followed by photooxygenation of 14 results in a complementary route to the basic skeleton 15 of nonaromatic A-ring angucyclines. (C) 1997, Published by Elsevier Science Ltd.
• Convergent and rapid assembly of benzonaphthopyranone cores of chartreusin, chrymutasins and hayumicins
  作者：Dipakranjan Mal、Asit Patra、Haren Roy

  DOI：10.1016/j.tetlet.2004.08.142

  日期：2004.10

  A new methodology for the rapid regiospecific synthesis of benzonaphthopyranones has been developed, on the basis of a tactical extension of the Hauser-Kraus annulation. The prowess of the methodology has been illustrated by a short synthesis of chartarin (22b) and a facile entry to the chrymutasin scaffold (26). (C) 2004 Elsevier Ltd. All rights reserved.
• Tandem annulation strategy for the convergent synthesis of benzonaphthopyranones: total synthesis of chartarin and O-methylhayumicinone
  作者：Sutapa Ray、Asit Patra、Dipakranjan Mal

  DOI：10.1016/j.tet.2008.01.039

  日期：2008.3

  A Hauser-initiated tandem annulation has been developed for the rapid regiospecific synthesis of benzonaphthopyranones via formation of two rings in one-pot operation. This strategy has been generalized with benzonaphthopyranones 26, 29, 32, and 35. It has also been employed in a short synthesis of chartarin (3) and O-methylhayumicinone (67).

  豪瑟（Hauser）引发的串联环已开发出来，用于通过一锅操作形成两个环来快速区域特异性合成苯并萘并吡喃酮。这种策略已经被推广以benzonaphthopyranones 26，29，32，和35。它也已被用于沙丁鱼酯（3）和O-甲基干草umi酮（67）的短合成中。