furanaphin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: furanaphin
• 英文别名: 5,7-dihydroxy-3-methylnaphtho[2,3-c]furan-4(1H)-one；6,8-dihydroxy-1-methyl-3H-benzo[f][2]benzofuran-9-one
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: GYMFDZAJYXZWMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  furanaphin 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 0.1h， 生成 3-Methyl-1,3-dihydro-naphtho[2,3-c]furan-4,5,7-triol
  参考文献：
  名称：

  Furanaphin: a novel naphtho[2,3-c]furan-4(1H)-one derivative from the aphid Aphis spiraecola Patch

  摘要：

  A novel naphtho[2,3-c]furan-4(1H)-one derivative 1, named furanaphin, was isolated from the aphid A. spiraecola P. The structure of the compound was established by a single crystal X-ray analysis of its (S)-MTPA ester. Furanaphin was found to have cytotoxicity against HL-60 human tumor cells. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.061
• 作为产物：
  描述：

  [4,5-Bis[[tert-butyl(dimethyl)silyl]oxy]-3-[1-[tert-butyl(dimethyl)silyl]oxyethenyl]-7-methoxynaphthalen-2-yl]methanol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以50%的产率得到furanaphin
  参考文献：
  名称：

  三氟化硼-乙酸配合物辅助薯条重排全合成黄色蚜虫色素呋喃酚

  摘要：

  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。

  DOI：

  10.1055/s-0031-1290429

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。
• Furanaphin: a novel naphtho[2,3-c]furan-4(1H)-one derivative from the aphid Aphis spiraecola Patch
  作者：Mitsuyo Horikawa、Tadashi Noguchi、Shigeru Takaoka、Masaki Kawase、Masao Sato、Tetsuto Tsunoda

  DOI：10.1016/j.tet.2003.11.061

  日期：2004.1

  A novel naphtho[2,3-c]furan-4(1H)-one derivative 1, named furanaphin, was isolated from the aphid A. spiraecola P. The structure of the compound was established by a single crystal X-ray analysis of its (S)-MTPA ester. Furanaphin was found to have cytotoxicity against HL-60 human tumor cells. (C) 2003 Elsevier Ltd. All rights reserved.