1-乙酰氧基-6,8-二甲氧基-3-甲基-萘 | 106593-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-乙酰氧基-6,8-二甲氧基-3-甲基-萘
• 英文名称: 1-acetoxy-6,8-dimethoxy-3-methyl-naphthalene
• 英文别名: 1-Acetoxy-6,8-dimethoxy-3-methyl-naphthalin；(6,8-Dimethoxy-3-methylnaphthalen-1-yl) acetate；(6,8-dimethoxy-3-methylnaphthalen-1-yl) acetate
• CAS: 106593-01-5
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: KAWVXNUCVZNLBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  402.8±40.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-乙酰氧基-6,8-二甲氧基-3-甲基-萘 在 boron trifluoride diacetate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到1-(1-羟基-6,8-二甲氧基-3-甲基萘-2-基)乙酮
  参考文献：
  名称：

  Xanthouroleuconaphin: a yellowish pigment from the aphid Uroleucon nigrotuberculatum and its total synthesis

  摘要：

  A novel yellowish pigment, xanthouroleuconaphin, was isolated from the aphid Uroleucon nigrotuberculatum. Its structure was established by detailed analyses of 1D and 2D NMR spectra and EI-HRMS. Furthermore, the total synthesis of (+/-)-xanthouroleuconaphin was accomplished via oxidative phenolic coupling of 6-hydroxymusizin, which was prepared by the Fries rearrangement using BF3 center dot 2AcOH complex. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.070
• 作为产物：
  描述：

  4-(3,5-dimethoxy-phenyl)-3-methyl-butyric acid 在 二硫化碳 、 PPA 、 溴 、 sodium acetate 作用下， 生成 1-乙酰氧基-6,8-二甲氧基-3-甲基-萘
  参考文献：
  名称：

  Frei; Schmid, Justus Liebigs Annalen der Chemie, 1957, vol. 603, p. 169,176

  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。
• Xanthouroleuconaphin: a yellowish pigment from the aphid Uroleucon nigrotuberculatum and its total synthesis
  作者：Taichi Nishimura、Mitsuyo Horikawa、Kouji Yamada、Ayaka Sogabe、Takeshi Nishii、Hiroto Kaku、Makoto Inai、Masami Tanaka、Shigeru Takahashi、Tetsuto Tsunoda

  DOI：10.1016/j.tet.2012.12.070

  日期：2013.2

  A novel yellowish pigment, xanthouroleuconaphin, was isolated from the aphid Uroleucon nigrotuberculatum. Its structure was established by detailed analyses of 1D and 2D NMR spectra and EI-HRMS. Furthermore, the total synthesis of (+/-)-xanthouroleuconaphin was accomplished via oxidative phenolic coupling of 6-hydroxymusizin, which was prepared by the Fries rearrangement using BF3 center dot 2AcOH complex. (C) 2013 Elsevier Ltd. All rights reserved.
• Frei; Schmid, Justus Liebigs Annalen der Chemie, 1957, vol. 603, p. 169,176
  作者：Frei、Schmid

  DOI：——

  日期：——