4-羟基-5,7-二甲氧基-2-萘羧酸乙酯 | 94002-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-羟基-5,7-二甲氧基-2-萘羧酸乙酯
• 英文名称: 4-Hydroxy-5,7-dimethoxy-naphthoesaeure-ethylester
• 英文别名: 4-hydroxy-5,7-dimethoxy-[2]naphthoic acid ethyl ester；4-Hydroxy-5,7-dimethoxy-[2]naphthoesaeure-aethylester；4-Hydroxy-5,7-dimethoxy-2-naphthalenecarboxylic acid ethyl ester；ethyl 4-hydroxy-5,7-dimethoxynaphthalene-2-carboxylate
• CAS: 94002-68-3
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: VEJIXTZHZCCQFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-羟基-5,7-二甲氧基-2-萘羧酸乙酯 在 氢氧化钾 作用下， 生成 4-羟基-5,7-二甲氧基-2-萘羧酸
  参考文献：
  名称：

  Effect of water density inversion on the plane-parallel flow and heat transfer in a channel of constant width

  摘要：

  DOI：

  10.1007/bf02698787
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 二硫化碳 、 溴 作用下， 生成 4-羟基-5,7-二甲氧基-2-萘羧酸乙酯
  参考文献：
  名称：

  Horii et al., Chemical and pharmaceutical bulletin, 1963, vol. 11, p. 309,311

  摘要：

  DOI：

文献信息

• A Total Synthesis of Yellowish Aphid Pigment Furanaphin through Fries Rearrangement Assisted by Boron Trifluoride-Acetic Acid Complex
  作者：Tetsuto Tsunoda、Taichi Nishimura、Takeki Iwata、Hironori Maegawa、Takeshi Nishii、Masami Matsugasako、Hiroto Kaku、Mitsuyo Horikawa、Makoto Inai

  DOI：10.1055/s-0031-1290429

  日期：2012.7

  The yellowish aphid pigment furanaphin, isolated from Aphis spiraecola and possessing cytotoxicity against HL-60 (human promyelocytic leukemia-60) cells, was synthesized by utilizing the Fries rearrangement assisted with a BF3·2AcOH complex as a key step. It was confirmed that the complex effectively mediated the reaction even though the compounds had an electron-withdrawing substituent.

  以BF3·2AcOH复合物辅助的Fries重排为关键步骤，从Aphis spiraecola中分离出对HL-60（human promyelocyticemia-60）细胞具有细胞毒性的黄色蚜虫色素呋喃酚。证实即使化合物具有吸电子取代基，该配合物也有效地介导了反应。
• Total Synthesis and Structural Confirmation of the Antimalarial Naphthopyrone Lasionectrin
  作者：Vincent L. Poral、Daniel P. Furkert、Margaret A. Brimble

  DOI：10.1021/acs.orglett.5b03202

  日期：2015.12.18

  The total synthesis of lasionectrin, a naphthopyrone metabolite of an Acremonium-like fungus collected in Equatorial Guinea, is reported. Divergent access to four stereoisomers confirmed the natural product to be the enantiomer of the originally proposed structure. Highlights of the synthesis include ring opening of a chiral oxetane using a thiol, a highly E-selective Julia-Kocienski olefination, and a modified Sharpless/Upjohn dihydroxylation. Palladium-catalyzed carbonylative lactonization was used to assemble the fused naphthopyrone ring system.